# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email RMV@IITB.AC.IN _publ_contact_author_name 'Prof Ramaswamy Murugavel' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_address ; Department of Chemistry IIT-Bombay Powai Mumbai 400 076 INDIA ; _publ_section_title ; O-H Bond elongation in co-ordinated water through intramolecular P=O H-O bonding. 'Snap-shots' in phosphate ester hydrolysis ; loop_ _publ_author_name '' 'Ramaswamy Murugavel' 'R. Butcher' 'Ramasamy Pothiraja' 'Malaichamy Sathiyendiran' data_293K_structure_of_2 _database_code_CSD 211839 _chemical_name_common cu-phenanthroline-dtbp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H46 Cu N2 O9 P2' _chemical_formula_weight 680.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.7666(11) _cell_length_b 18.0616(10) _cell_length_c 17.5747(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.078(6) _cell_angle_gamma 90.00 _cell_volume 3391.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour blue _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1436 _exptl_absorpt_coefficient_mu 0.788 _exptl_absorpt_correction_type ? _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 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius Turbo CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6251 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.1009 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.94 _reflns_number_total 5914 _reflns_number_gt 3453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0568P)^2^+4.8418P] 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 5914 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1438 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1254 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.78435(5) 0.88703(4) 0.57095(3) 0.0381(2) Uani 1 1 d . . . P1 P 0.94531(13) 0.75616(9) 0.50044(9) 0.0470(4) Uani 1 1 d . . . P2 P 0.90208(13) 0.92119(8) 0.74066(8) 0.0404(4) Uani 1 1 d . . . O1 O 0.8331(3) 0.77889(19) 0.5374(2) 0.0452(9) Uani 1 1 d . . . O2 O 1.0398(4) 0.8137(3) 0.4942(3) 0.0901(17) Uani 1 1 d . . . O3 O 0.9095(4) 0.7232(3) 0.4198(3) 0.0939(18) Uani 1 1 d . . . O4 O 1.0038(7) 0.6842(4) 0.5378(3) 0.151(3) Uani 1 1 d . . . O5 O 0.7958(3) 0.8928(2) 0.68376(18) 0.0454(9) Uani 1 1 d . . . O6 O 1.0302(3) 0.9180(2) 0.7165(2) 0.0492(10) Uani 1 1 d . . . O7 O 0.8626(3) 1.0033(2) 0.7579(2) 0.0505(10) Uani 1 1 d . . . O8 O 0.9058(3) 0.8781(2) 0.81882(19) 0.0498(10) Uani 1 1 d . . . O9 O 0.9561(4) 0.9235(2) 0.5663(3) 0.0455(11) Uani 1 1 d . . . N1 N 0.6014(4) 0.8627(2) 0.5659(2) 0.0395(10) Uani 1 1 d . . . N2 N 0.7198(4) 0.9384(2) 0.4679(2) 0.0376(10) Uani 1 1 d . . . C1 C 0.5466(5) 0.8231(3) 0.6153(3) 0.0505(15) Uani 1 1 d . . . H1 H 0.5950 0.8049 0.6587 0.061 Uiso 1 1 calc R . . C2 C 0.4179(5) 0.8074(4) 0.6047(3) 0.0569(16) Uani 1 1 d . . . H2 H 0.3824 0.7782 0.6399 0.068 Uiso 1 1 calc R . . C3 C 0.3451(5) 0.8356(3) 0.5416(4) 0.0574(16) Uani 1 1 d . . . H3 H 0.2594 0.8265 0.5345 0.069 Uiso 1 1 calc R . . C4 C 0.4002(5) 0.8779(3) 0.4882(3) 0.0435(13) Uani 1 1 d . . . C5 C 0.5303(4) 0.8892(3) 0.5023(3) 0.0360(12) Uani 1 1 d . . . C6 C 0.5935(4) 0.9302(3) 0.4498(3) 0.0352(12) Uani 1 1 d . . . C7 C 0.5268(5) 0.9602(3) 0.3827(3) 0.0445(14) Uani 1 1 d . . . C8 C 0.3929(5) 0.9492(3) 0.3704(3) 0.0543(16) Uani 1 1 d . . . H8 H 0.3468 0.9695 0.3272 0.065 Uiso 1 1 calc R . . C9 C 0.3337(5) 0.9102(3) 0.4201(4) 0.0551(17) Uani 1 1 d . . . H9 H 0.2475 0.9039 0.4103 0.066 Uiso 1 1 calc R . . C10 C 0.5964(6) 0.9994(3) 0.3344(3) 0.0576(16) Uani 1 1 d . . . H10 H 0.5567 1.0204 0.2896 0.069 Uiso 1 1 calc R . . C11 C 0.7230(6) 1.0071(3) 0.3526(3) 0.0588(16) Uani 1 1 d . . . H11 H 0.7694 1.0333 0.3204 0.071 Uiso 1 1 calc R . . C12 C 0.7814(5) 0.9756(3) 0.4194(3) 0.0476(14) Uani 1 1 d . . . H12 H 0.8677 0.9807 0.4308 0.057 Uiso 1 1 calc R . . C13 C 0.7941(6) 0.6957(4) 0.3810(4) 0.0638(18) Uani 1 1 d . . . C14 C 0.7386(9) 0.6389(6) 0.4281(5) 0.129(4) Uani 1 1 d . . . H14A H 0.7131 0.6619 0.4729 0.194 Uiso 1 1 calc R . . H14B H 0.7997 0.6013 0.4432 0.194 Uiso 1 1 calc R . . H14C H 0.6672 0.6169 0.3984 0.194 Uiso 1 1 calc R . . C15 C 0.6979(9) 0.7567(5) 0.3664(5) 0.136(4) Uani 1 1 d . . . H15A H 0.7349 0.7986 0.3441 0.203 Uiso 1 1 calc R . . H15B H 0.6697 0.7711 0.4140 0.203 Uiso 1 1 calc R . . H15C H 0.6281 0.7392 0.3318 0.203 Uiso 1 1 calc R . . C16 C 0.8256(8) 0.6625(7) 0.3078(5) 0.146(5) Uani 1 1 d . . . H16A H 0.8690 0.6984 0.2806 0.219 Uiso 1 1 calc R . . H16B H 0.7499 0.6479 0.2767 0.219 Uiso 1 1 calc R . . H16C H 0.8780 0.6199 0.3190 0.219 Uiso 1 1 calc R . . C17 C 1.0397(6) 0.6592(4) 0.6132(4) 0.0637(18) Uani 1 1 d . . . C18 C 0.9693(10) 0.6932(8) 0.6732(5) 0.176(6) Uani 1 1 d . . . H18A H 0.9921 0.7445 0.6797 0.265 Uiso 1 1 calc R . . H18B H 0.9900 0.6676 0.7210 0.265 Uiso 1 1 calc R . . H18C H 0.8810 0.6894 0.6574 0.265 Uiso 1 1 calc R . . C19 C 1.1690(9) 0.6729(10) 0.6338(6) 0.221(8) Uani 1 1 d . . . H19A H 1.1825 0.7251 0.6410 0.332 Uiso 1 1 calc R . . H19B H 1.2148 0.6556 0.5937 0.332 Uiso 1 1 calc R . . H19C H 1.1974 0.6473 0.6806 0.332 Uiso 1 1 calc R . . C20 C 1.021(2) 0.5819(8) 0.6061(10) 0.330(14) Uani 1 1 d . . . H20A H 1.0418 0.5589 0.6553 0.494 Uiso 1 1 calc R . . H20B H 1.0744 0.5623 0.5709 0.494 Uiso 1 1 calc R . . H20C H 0.9355 0.5719 0.5873 0.494 Uiso 1 1 calc R . . C21 C 0.9435(6) 1.0625(3) 0.7937(4) 0.0594(17) Uani 1 1 d . . . C22 C 1.0090(7) 1.0989(5) 0.7316(4) 0.097(3) Uiso 1 1 d . . . H22A H 0.9477 1.1152 0.6906 0.146 Uiso 1 1 calc R . . H22B H 1.0643 1.0639 0.7122 0.146 Uiso 1 1 calc R . . H22C H 1.0563 1.1407 0.7527 0.146 Uiso 1 1 calc R . . C23 C 1.0380(8) 1.0337(4) 0.8575(4) 0.108(3) Uani 1 1 d . . . H23A H 1.0956 1.0012 0.8365 0.162 Uiso 1 1 calc R . . H23B H 0.9955 1.0071 0.8939 0.162 Uiso 1 1 calc R . . H23C H 1.0831 1.0745 0.8827 0.162 Uiso 1 1 calc R . . C24 C 0.8546(8) 1.1166(4) 0.8229(6) 0.121(3) Uani 1 1 d . . . H24A H 0.8123 1.0932 0.8614 0.181 Uiso 1 1 calc R . . H24B H 0.7943 1.1325 0.7813 0.181 Uiso 1 1 calc R . . H24C H 0.9005 1.1587 0.8447 0.181 Uiso 1 1 calc R . . C25 C 0.8030(6) 0.8520(4) 0.8597(3) 0.0582(16) Uani 1 1 d . . . C26 C 0.6926(7) 0.9041(4) 0.8504(5) 0.097(3) Uani 1 1 d . . . H26A H 0.6611 0.9082 0.7971 0.145 Uiso 1 1 calc R . . H26B H 0.7185 0.9520 0.8701 0.145 Uiso 1 1 calc R . . H26C H 0.6281 0.8852 0.8782 0.145 Uiso 1 1 calc R . . C27 C 0.7672(8) 0.7758(4) 0.8280(4) 0.096(3) Uani 1 1 d . . . H27A H 0.7393 0.7796 0.7741 0.144 Uiso 1 1 calc R . . H27B H 0.7010 0.7561 0.8539 0.144 Uiso 1 1 calc R . . H27C H 0.8386 0.7437 0.8359 0.144 Uiso 1 1 calc R . . C28 C 0.8613(8) 0.8457(5) 0.9419(4) 0.104(3) Uani 1 1 d . . . H28A H 0.8874 0.8938 0.9608 0.156 Uiso 1 1 calc R . . H28B H 0.9324 0.8133 0.9448 0.156 Uiso 1 1 calc R . . H28C H 0.8010 0.8259 0.9724 0.156 Uiso 1 1 calc R . . H9A H 1.006(8) 0.883(5) 0.537(4) 0.12(3) Uiso 1 1 d . . . H9B H 0.984(5) 0.920(3) 0.603(3) 0.029(18) 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 0.0284(3) 0.0437(4) 0.0401(4) 0.0023(3) -0.0040(2) -0.0059(3) P1 0.0350(8) 0.0564(10) 0.0473(9) -0.0078(7) -0.0043(6) 0.0034(7) P2 0.0360(7) 0.0434(8) 0.0389(8) 0.0004(6) -0.0069(6) -0.0007(6) O1 0.043(2) 0.041(2) 0.051(2) -0.0067(18) 0.0061(17) -0.0056(17) O2 0.044(3) 0.099(4) 0.133(4) -0.058(3) 0.036(3) -0.033(3) O3 0.041(2) 0.155(5) 0.087(3) -0.074(3) 0.013(2) -0.027(3) O4 0.179(6) 0.180(7) 0.102(4) 0.050(4) 0.046(4) 0.132(6) O5 0.0382(19) 0.058(2) 0.0378(19) 0.0008(18) -0.0044(16) -0.0095(18) O6 0.036(2) 0.060(2) 0.050(2) -0.0048(19) -0.0027(17) -0.0004(18) O7 0.040(2) 0.044(2) 0.063(2) -0.0029(19) -0.0109(18) -0.0026(18) O8 0.047(2) 0.060(3) 0.040(2) 0.0092(19) -0.0053(17) 0.001(2) O9 0.033(2) 0.058(3) 0.043(3) 0.003(2) -0.005(2) -0.0116(19) N1 0.031(2) 0.044(3) 0.043(3) 0.006(2) 0.000(2) -0.006(2) N2 0.034(2) 0.039(3) 0.038(2) 0.000(2) -0.0010(19) -0.004(2) C1 0.037(3) 0.057(4) 0.055(4) 0.006(3) -0.003(3) -0.010(3) C2 0.042(3) 0.068(4) 0.061(4) 0.007(3) 0.008(3) -0.010(3) C3 0.036(3) 0.067(4) 0.068(4) -0.012(3) 0.002(3) -0.007(3) C4 0.034(3) 0.046(3) 0.048(3) -0.012(3) -0.005(2) 0.001(3) C5 0.028(3) 0.037(3) 0.041(3) -0.011(3) -0.002(2) 0.000(2) C6 0.032(3) 0.034(3) 0.038(3) -0.009(2) 0.000(2) 0.005(2) C7 0.045(3) 0.042(3) 0.042(3) -0.006(3) -0.010(3) 0.008(3) C8 0.051(4) 0.056(4) 0.050(4) -0.009(3) -0.017(3) 0.013(3) C9 0.030(3) 0.064(4) 0.066(4) -0.021(3) -0.015(3) 0.010(3) C10 0.073(4) 0.050(4) 0.046(3) 0.006(3) -0.006(3) 0.003(3) C11 0.068(4) 0.062(4) 0.048(4) 0.013(3) 0.009(3) -0.007(3) C12 0.042(3) 0.051(4) 0.049(3) 0.005(3) 0.004(3) -0.003(3) C13 0.054(4) 0.072(5) 0.061(4) -0.024(4) -0.009(3) -0.002(4) C14 0.122(8) 0.127(8) 0.128(8) -0.010(7) -0.023(6) -0.062(7) C15 0.152(9) 0.129(8) 0.107(7) -0.026(6) -0.056(6) 0.053(7) C16 0.084(6) 0.253(13) 0.097(7) -0.112(8) -0.005(5) -0.010(7) C17 0.055(4) 0.078(5) 0.057(4) 0.023(4) 0.000(3) 0.005(4) C18 0.144(10) 0.294(17) 0.102(8) 0.077(9) 0.057(7) 0.075(10) C19 0.068(7) 0.47(3) 0.125(9) 0.028(13) -0.008(6) -0.055(11) C20 0.63(4) 0.134(13) 0.221(18) -0.012(12) 0.03(2) -0.14(2) C21 0.053(4) 0.048(4) 0.074(4) -0.012(3) -0.002(3) -0.001(3) C23 0.128(7) 0.077(5) 0.101(6) -0.013(5) -0.064(5) -0.024(5) C24 0.108(7) 0.070(6) 0.187(10) -0.047(6) 0.026(7) 0.001(5) C25 0.063(4) 0.064(4) 0.046(4) 0.007(3) 0.003(3) -0.006(3) C26 0.071(5) 0.105(7) 0.121(7) 0.035(5) 0.045(5) 0.015(5) C27 0.117(7) 0.069(5) 0.100(6) 0.010(5) 0.008(5) -0.026(5) C28 0.106(6) 0.155(8) 0.051(4) 0.024(5) 0.010(4) -0.010(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 Cu1 O5 1.974(3) . ? Cu1 O9 1.975(4) . ? Cu1 N1 2.009(4) . ? Cu1 N2 2.077(4) . ? Cu1 O1 2.125(3) . ? P1 O2 1.468(4) . ? P1 O1 1.498(4) . ? P1 O3 1.541(4) . ? P1 O4 1.554(6) . ? P2 O6 1.494(4) . ? P2 O5 1.514(3) . ? P2 O8 1.575(4) . ? P2 O7 1.581(4) . ? O3 C13 1.431(7) . ? O4 C17 1.409(7) . ? O7 C21 1.471(7) . ? O8 C25 1.469(7) . ? O9 H9A 1.07(9) . ? O9 H9B 0.69(5) . ? N1 C1 1.319(6) . ? N1 C5 1.361(6) . ? N2 C12 1.326(6) . ? N2 C6 1.365(6) . ? C1 C2 1.404(7) . ? C1 H1 0.9300 . ? C2 C3 1.374(8) . ? C2 H2 0.9300 . ? C3 C4 1.398(8) . ? C3 H3 0.9300 . ? C4 C5 1.407(7) . ? C4 C9 1.441(7) . ? C5 C6 1.422(7) . ? C6 C7 1.411(7) . ? C7 C10 1.393(8) . ? C7 C8 1.445(7) . ? C8 C9 1.342(8) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.368(8) . ? C10 H10 0.9300 . ? C11 C12 1.385(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.488(10) . ? C13 C16 1.495(9) . ? C13 C15 1.513(10) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C20 1.415(14) . ? C17 C19 1.416(10) . ? C17 C18 1.503(11) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C24 1.501(9) . ? C21 C23 1.512(9) . ? C21 C22 1.520(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C28 1.506(8) . ? C25 C26 1.509(9) . ? C25 C27 1.516(9) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 O5 Cu1 O9 94.66(17) . . ? O5 Cu1 N1 89.74(15) . . ? O9 Cu1 N1 171.59(18) . . ? O5 Cu1 N2 145.58(16) . . ? O9 Cu1 N2 91.70(17) . . ? N1 Cu1 N2 80.67(16) . . ? O5 Cu1 O1 109.92(15) . . ? O9 Cu1 O1 91.75(17) . . ? N1 Cu1 O1 93.49(15) . . ? N2 Cu1 O1 103.65(15) . . ? O2 P1 O1 116.2(2) . . ? O2 P1 O3 107.5(3) . . ? O1 P1 O3 112.4(2) . . ? O2 P1 O4 112.0(4) . . ? O1 P1 O4 110.6(3) . . ? O3 P1 O4 96.2(4) . . ? O6 P2 O5 116.7(2) . . ? O6 P2 O8 107.7(2) . . ? O5 P2 O8 110.2(2) . . ? O6 P2 O7 111.7(2) . . ? O5 P2 O7 104.2(2) . . ? O8 P2 O7 105.9(2) . . ? P1 O1 Cu1 127.8(2) . . ? C13 O3 P1 132.5(4) . . ? C17 O4 P1 135.7(6) . . ? P2 O5 Cu1 129.0(2) . . ? C21 O7 P2 127.3(3) . . ? C25 O8 P2 130.2(3) . . ? Cu1 O9 H9A 109(4) . . ? Cu1 O9 H9B 104(4) . . ? H9A O9 H9B 102(6) . . ? C1 N1 C5 118.6(4) . . ? C1 N1 Cu1 127.2(4) . . ? C5 N1 Cu1 114.1(3) . . ? C12 N2 C6 117.9(4) . . ? C12 N2 Cu1 130.3(3) . . ? C6 N2 Cu1 111.9(3) . . ? N1 C1 C2 122.5(5) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.2(6) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.8(5) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 117.2(5) . . ? C3 C4 C9 124.8(5) . . ? C5 C4 C9 118.1(5) . . ? N1 C5 C4 122.8(5) . . ? N1 C5 C6 116.8(4) . . ? C4 C5 C6 120.5(5) . . ? N2 C6 C7 122.9(5) . . ? N2 C6 C5 116.6(4) . . ? C7 C6 C5 120.5(5) . . ? C10 C7 C6 116.5(5) . . ? C10 C7 C8 125.6(5) . . ? C6 C7 C8 117.9(5) . . ? C9 C8 C7 121.4(5) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C4 121.7(5) . . ? C8 C9 H9 119.2 . . ? C4 C9 H9 119.2 . . ? C11 C10 C7 120.3(5) . . ? C11 C10 H10 119.8 . . ? C7 C10 H10 119.8 . . ? C10 C11 C12 119.5(6) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N2 C12 C11 122.8(5) . . ? N2 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? O3 C13 C14 111.1(6) . . ? O3 C13 C16 105.9(6) . . ? C14 C13 C16 110.6(7) . . ? O3 C13 C15 111.3(6) . . ? C14 C13 C15 106.4(7) . . ? C16 C13 C15 111.6(7) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 C20 102.4(9) . . ? O4 C17 C19 109.3(7) . . ? C20 C17 C19 108.5(13) . . ? O4 C17 C18 115.2(6) . . ? C20 C17 C18 112.9(11) . . ? C19 C17 C18 108.3(9) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O7 C21 C24 104.6(5) . . ? O7 C21 C23 112.0(5) . . ? C24 C21 C23 111.7(7) . . ? O7 C21 C22 108.1(5) . . ? C24 C21 C22 109.7(6) . . ? C23 C21 C22 110.6(6) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 C28 104.1(5) . . ? O8 C25 C26 112.2(5) . . ? C28 C25 C26 112.3(6) . . ? O8 C25 C27 106.5(5) . . ? C28 C25 C27 109.9(6) . . ? C26 C25 C27 111.4(6) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O9 H9A O2 1.07(9) 1.53(9) 2.575(6) 162(7) . O9 H9B O6 0.69(5) 1.99(5) 2.664(6) 167(6) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.992 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.075 ##==END data_203K_structure_of_2 _database_code_CSD 211840 _chemical_name_common cu-phenanthroline-dtbp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H46 Cu N2 O9 P2' _chemical_formula_weight 680.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.569(2) _cell_length_b 17.705(4) _cell_length_c 17.346(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.62(3) _cell_angle_gamma 90.00 _cell_volume 3230.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1436 _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 STOE-AED-2 _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5971 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5460 _reflns_number_gt 4883 _reflns_threshold_expression >2sigma(I) _computing_data_collection DIF4 _computing_cell_refinement DIF4 _computing_data_reduction REDU4 _computing_structure_solution SHELXS-97 _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^)+(0.0936P)^2^+3.6666P] 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 5460 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.77642(3) 0.88756(2) 0.572361(19) 0.02150(15) Uani 1 1 d . . . P1 P 0.95244(7) 0.75970(5) 0.50244(4) 0.0236(2) Uani 1 1 d . . . P2 P 0.89785(7) 0.91679(5) 0.74190(4) 0.0223(2) Uani 1 1 d . . . O1 O 0.83615(18) 0.77706(12) 0.54179(12) 0.0242(5) Uani 1 1 d . . . O2 O 1.0194(2) 0.82618(14) 0.47193(13) 0.0341(5) Uani 1 1 d . . . O3 O 0.9235(2) 0.69835(14) 0.43708(13) 0.0360(6) Uani 1 1 d . . . O4 O 1.0608(2) 0.71918(14) 0.55827(13) 0.0342(5) Uani 1 1 d . . . O5 O 0.7894(2) 0.88791(13) 0.68599(12) 0.0280(5) Uani 1 1 d . . . O6 O 1.02708(19) 0.91520(13) 0.71548(12) 0.0284(5) Uani 1 1 d . . . O7 O 0.85527(19) 0.99986(12) 0.76123(12) 0.0265(5) Uani 1 1 d . . . O8 O 0.9031(2) 0.87178(13) 0.82046(12) 0.0280(5) Uani 1 1 d . . . O9 O 0.9486(2) 0.92893(13) 0.56579(14) 0.0268(5) Uani 1 1 d . . . N1 N 0.5911(2) 0.86159(15) 0.56968(15) 0.0250(6) Uani 1 1 d . . . N2 N 0.7132(2) 0.93472(14) 0.46766(14) 0.0234(5) Uani 1 1 d . . . C1 C 0.5337(3) 0.8237(2) 0.62197(19) 0.0323(7) Uani 1 1 d . . . H1 H 0.5823 0.8060 0.6666 0.039 Uiso 1 1 calc R . . C2 C 0.4032(3) 0.8090(2) 0.6129(2) 0.0376(8) Uani 1 1 d . . . H2 H 0.3659 0.7810 0.6508 0.045 Uiso 1 1 calc R . . C3 C 0.3297(3) 0.8351(2) 0.5494(2) 0.0355(8) Uani 1 1 d . . . H3 H 0.2417 0.8256 0.5433 0.043 Uiso 1 1 calc R . . C4 C 0.3879(3) 0.87648(19) 0.4933(2) 0.0292(7) Uani 1 1 d . . . C5 C 0.5191(3) 0.88754(16) 0.50607(18) 0.0241(7) Uani 1 1 d . . . C6 C 0.5856(3) 0.92733(17) 0.45071(17) 0.0223(6) Uani 1 1 d . . . C7 C 0.5183(3) 0.95635(18) 0.38373(18) 0.0281(7) Uani 1 1 d . . . C8 C 0.3832(3) 0.9458(2) 0.3726(2) 0.0349(8) Uani 1 1 d . . . H8 H 0.3369 0.9657 0.3282 0.042 Uiso 1 1 calc R . . C9 C 0.3217(3) 0.9080(2) 0.4246(2) 0.0343(8) Uani 1 1 d . . . H9 H 0.2331 0.9019 0.4158 0.041 Uiso 1 1 calc R . . C10 C 0.5903(3) 0.9946(2) 0.33216(19) 0.0337(8) Uani 1 1 d . . . H10 H 0.5501 1.0152 0.2861 0.040 Uiso 1 1 calc R . . C11 C 0.7191(3) 1.0021(2) 0.34906(19) 0.0345(8) Uani 1 1 d . . . H11 H 0.7677 1.0277 0.3147 0.041 Uiso 1 1 calc R . . C12 C 0.7775(3) 0.97127(19) 0.41777(18) 0.0294(7) Uani 1 1 d . . . H12 H 0.8659 0.9768 0.4289 0.035 Uiso 1 1 calc R . . C13 C 0.8035(3) 0.6902(2) 0.38688(19) 0.0343(8) Uani 1 1 d . . . C14 C 0.7096(4) 0.6504(3) 0.4316(3) 0.0644(14) Uani 1 1 d . . . H14A H 0.6945 0.6802 0.4768 0.097 Uiso 1 1 calc R . . H14B H 0.7429 0.6013 0.4480 0.097 Uiso 1 1 calc R . . H14C H 0.6303 0.6440 0.3991 0.097 Uiso 1 1 calc R . . C15 C 0.7566(6) 0.7654(3) 0.3569(3) 0.0807(18) Uani 1 1 d . . . H15A H 0.8227 0.7902 0.3312 0.121 Uiso 1 1 calc R . . H15B H 0.7345 0.7964 0.3997 0.121 Uiso 1 1 calc R . . H15C H 0.6820 0.7583 0.3203 0.121 Uiso 1 1 calc R . . C16 C 0.8378(5) 0.6403(4) 0.3217(3) 0.0768(17) Uani 1 1 d . . . H16A H 0.9055 0.6638 0.2963 0.115 Uiso 1 1 calc R . . H16B H 0.7639 0.6335 0.2845 0.115 Uiso 1 1 calc R . . H16C H 0.8661 0.5916 0.3422 0.115 Uiso 1 1 calc R . . C17 C 1.0437(3) 0.6627(2) 0.6176(2) 0.0330(8) Uani 1 1 d . . . C18 C 0.9802(4) 0.6999(3) 0.6828(2) 0.0484(10) Uani 1 1 d . . . H18A H 1.0276 0.7447 0.7002 0.073 Uiso 1 1 calc R . . H18B H 0.9788 0.6648 0.7256 0.073 Uiso 1 1 calc R . . H18C H 0.8939 0.7140 0.6643 0.073 Uiso 1 1 calc R . . C19 C 1.1783(4) 0.6388(3) 0.6446(3) 0.0683(14) Uani 1 1 d . . . H19A H 1.2249 0.6817 0.6678 0.102 Uiso 1 1 calc R . . H19B H 1.2198 0.6206 0.6008 0.102 Uiso 1 1 calc R . . H19C H 1.1763 0.5988 0.6827 0.102 Uiso 1 1 calc R . . C20 C 0.9675(4) 0.5973(3) 0.5840(3) 0.0546(11) Uani 1 1 d . . . H20A H 0.8799 0.6128 0.5715 0.082 Uiso 1 1 calc R . . H20B H 0.9709 0.5565 0.6215 0.082 Uiso 1 1 calc R . . H20C H 1.0023 0.5801 0.5374 0.082 Uiso 1 1 calc R . . C21 C 0.9359(3) 1.05930(19) 0.79872(19) 0.0306(7) Uani 1 1 d . . . C22 C 1.0066(4) 1.0973(2) 0.7373(2) 0.0436(9) Uiso 1 1 d . . . H22A H 0.9462 1.1147 0.6954 0.065 Uiso 1 1 calc R . . H22B H 1.0648 1.0616 0.7174 0.065 Uiso 1 1 calc R . . H22C H 1.0541 1.1401 0.7600 0.065 Uiso 1 1 calc R . . C23 C 1.0267(4) 1.0280(2) 0.8637(2) 0.0509(11) Uani 1 1 d . . . H23A H 1.0835 0.9920 0.8428 0.076 Uiso 1 1 calc R . . H23B H 0.9788 1.0030 0.9012 0.076 Uiso 1 1 calc R . . H23C H 1.0760 1.0689 0.8887 0.076 Uiso 1 1 calc R . . C24 C 0.8419(5) 1.1129(2) 0.8290(3) 0.0624(14) Uani 1 1 d . . . H24A H 0.7975 1.0876 0.8680 0.094 Uiso 1 1 calc R . . H24B H 0.7810 1.1290 0.7867 0.094 Uiso 1 1 calc R . . H24C H 0.8866 1.1566 0.8517 0.094 Uiso 1 1 calc R . . C25 C 0.7972(3) 0.8461(2) 0.86248(19) 0.0319(7) Uani 1 1 d . . . C26 C 0.6904(4) 0.9033(2) 0.8589(3) 0.0485(10) Uani 1 1 d . . . H26A H 0.6560 0.9103 0.8054 0.073 Uiso 1 1 calc R . . H26B H 0.7228 0.9510 0.8799 0.073 Uiso 1 1 calc R . . H26C H 0.6239 0.8851 0.8890 0.073 Uiso 1 1 calc R . . C27 C 0.7519(4) 0.7709(2) 0.8285(2) 0.0495(10) Uani 1 1 d . . . H27A H 0.7170 0.7780 0.7752 0.074 Uiso 1 1 calc R . . H27B H 0.6867 0.7505 0.8583 0.074 Uiso 1 1 calc R . . H27C H 0.8228 0.7360 0.8303 0.074 Uiso 1 1 calc R . . C28 C 0.8544(4) 0.8360(3) 0.9451(2) 0.0512(10) Uani 1 1 d . . . H28A H 0.8871 0.8840 0.9653 0.077 Uiso 1 1 calc R . . H28B H 0.9232 0.7996 0.9466 0.077 Uiso 1 1 calc R . . H28C H 0.7897 0.8178 0.9765 0.077 Uiso 1 1 calc R . . H9A H 0.989(4) 0.897(2) 0.534(3) 0.045(12) Uiso 1 1 d . . . H9B H 0.984(4) 0.919(3) 0.608(3) 0.047(12) 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 0.0147(2) 0.0246(3) 0.0238(2) 0.00128(13) -0.00561(15) -0.00298(13) P1 0.0149(4) 0.0298(5) 0.0249(4) -0.0018(3) -0.0042(3) -0.0007(3) P2 0.0179(4) 0.0255(5) 0.0222(4) 0.0003(3) -0.0053(3) -0.0006(3) O1 0.0173(10) 0.0253(12) 0.0288(11) -0.0027(9) -0.0032(8) -0.0015(8) O2 0.0249(11) 0.0388(14) 0.0388(13) -0.0011(10) 0.0045(10) -0.0069(10) O3 0.0222(11) 0.0483(15) 0.0362(13) -0.0146(11) -0.0044(9) -0.0023(10) O4 0.0204(11) 0.0424(14) 0.0380(12) 0.0055(11) -0.0060(9) -0.0019(10) O5 0.0227(11) 0.0372(14) 0.0230(11) -0.0011(9) -0.0036(9) -0.0077(9) O6 0.0190(10) 0.0361(13) 0.0290(11) -0.0013(9) -0.0030(9) 0.0003(9) O7 0.0179(10) 0.0252(12) 0.0347(12) -0.0017(9) -0.0068(8) 0.0010(8) O8 0.0231(11) 0.0317(12) 0.0279(11) 0.0055(9) -0.0042(9) 0.0028(9) O9 0.0211(11) 0.0316(14) 0.0268(12) 0.0010(10) -0.0031(9) -0.0053(9) N1 0.0204(13) 0.0231(14) 0.0300(13) 0.0001(11) -0.0046(10) 0.0004(10) N2 0.0215(12) 0.0205(14) 0.0270(13) 0.0001(10) -0.0039(10) 0.0005(10) C1 0.0265(16) 0.0330(19) 0.0361(17) 0.0056(14) -0.0031(13) -0.0056(14) C2 0.0299(18) 0.034(2) 0.049(2) -0.0016(16) 0.0037(15) -0.0093(14) C3 0.0185(15) 0.035(2) 0.052(2) -0.0108(16) 0.0001(14) -0.0060(13) C4 0.0196(15) 0.0274(18) 0.0386(18) -0.0114(14) -0.0071(13) 0.0012(12) C5 0.0212(15) 0.0188(17) 0.0308(16) -0.0061(12) -0.0045(12) 0.0026(11) C6 0.0209(15) 0.0196(16) 0.0251(14) -0.0040(11) -0.0051(11) 0.0009(11) C7 0.0290(16) 0.0245(18) 0.0284(16) -0.0056(13) -0.0088(12) 0.0049(13) C8 0.0312(18) 0.034(2) 0.0354(18) -0.0076(15) -0.0179(14) 0.0128(15) C9 0.0202(16) 0.036(2) 0.043(2) -0.0142(16) -0.0140(14) 0.0062(14) C10 0.0413(19) 0.0309(19) 0.0265(16) 0.0015(13) -0.0084(14) 0.0065(15) C11 0.040(2) 0.031(2) 0.0322(17) 0.0053(14) 0.0002(14) 0.0021(15) C12 0.0244(16) 0.0301(18) 0.0327(16) 0.0021(13) -0.0019(13) -0.0009(13) C13 0.0243(16) 0.043(2) 0.0330(17) -0.0111(15) -0.0112(13) -0.0022(14) C14 0.041(2) 0.086(4) 0.063(3) -0.017(2) -0.009(2) -0.028(2) C15 0.101(4) 0.066(3) 0.062(3) 0.005(3) -0.055(3) 0.002(3) C16 0.047(3) 0.121(5) 0.059(3) -0.054(3) -0.010(2) 0.002(3) C17 0.0209(15) 0.039(2) 0.0376(18) 0.0112(15) -0.0043(13) -0.0017(13) C18 0.054(2) 0.055(3) 0.0344(19) 0.0082(17) -0.0018(17) -0.0045(19) C19 0.033(2) 0.090(4) 0.079(3) 0.038(3) -0.008(2) 0.008(2) C20 0.054(3) 0.047(3) 0.062(3) 0.003(2) 0.000(2) -0.010(2) C21 0.0236(16) 0.0275(18) 0.0400(18) -0.0059(14) -0.0013(13) -0.0038(13) C23 0.059(3) 0.047(2) 0.041(2) -0.0050(18) -0.0216(18) -0.0151(19) C24 0.050(3) 0.040(3) 0.100(4) -0.027(2) 0.023(3) -0.0052(19) C25 0.0311(17) 0.0315(19) 0.0326(17) 0.0057(14) 0.0015(13) -0.0042(14) C26 0.036(2) 0.044(2) 0.068(3) 0.010(2) 0.0196(19) 0.0053(17) C27 0.060(3) 0.040(2) 0.048(2) 0.0061(18) 0.0028(19) -0.0138(19) C28 0.054(2) 0.066(3) 0.0328(19) 0.0102(19) 0.0040(17) -0.007(2) _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 O5 1.962(2) . ? Cu1 O9 1.976(2) . ? Cu1 N1 2.008(3) . ? Cu1 N2 2.050(2) . ? Cu1 O1 2.138(2) . ? P1 O1 1.495(2) . ? P1 O2 1.497(2) . ? P1 O3 1.578(2) . ? P1 O4 1.596(2) . ? P2 O6 1.483(2) . ? P2 O5 1.516(2) . ? P2 O8 1.575(2) . ? P2 O7 1.584(2) . ? O3 C13 1.473(4) . ? O4 C17 1.458(4) . ? O7 C21 1.465(4) . ? O8 C25 1.467(4) . ? O9 H9A 0.92(5) . ? O9 H9B 0.81(5) . ? N1 C1 1.322(4) . ? N1 C5 1.357(4) . ? N2 C12 1.321(4) . ? N2 C6 1.358(4) . ? C1 C2 1.397(5) . ? C1 H1 0.9400 . ? C2 C3 1.365(5) . ? C2 H2 0.9400 . ? C3 C4 1.408(5) . ? C3 H3 0.9400 . ? C4 C5 1.397(4) . ? C4 C9 1.433(5) . ? C5 C6 1.430(4) . ? C6 C7 1.399(4) . ? C7 C10 1.404(5) . ? C7 C8 1.435(5) . ? C8 C9 1.341(5) . ? C8 H8 0.9400 . ? C9 H9 0.9400 . ? C10 C11 1.371(5) . ? C10 H10 0.9400 . ? C11 C12 1.398(4) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 C14 1.494(6) . ? C13 C15 1.496(6) . ? C13 C16 1.507(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 H16C 0.9700 . ? C17 C20 1.496(5) . ? C17 C19 1.514(5) . ? C17 C18 1.521(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 H20C 0.9700 . ? C21 C24 1.504(5) . ? C21 C23 1.512(5) . ? C21 C22 1.518(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 C28 1.511(5) . ? C25 C26 1.513(5) . ? C25 C27 1.515(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 H26C 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? 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 O5 Cu1 O9 94.75(10) . . ? O5 Cu1 N1 89.77(10) . . ? O9 Cu1 N1 170.28(10) . . ? O5 Cu1 N2 150.80(10) . . ? O9 Cu1 N2 91.15(10) . . ? N1 Cu1 N2 80.81(10) . . ? O5 Cu1 O1 105.00(9) . . ? O9 Cu1 O1 91.65(9) . . ? N1 Cu1 O1 95.50(9) . . ? N2 Cu1 O1 103.38(9) . . ? O1 P1 O2 115.98(13) . . ? O1 P1 O3 111.05(12) . . ? O2 P1 O3 110.64(14) . . ? O1 P1 O4 112.86(13) . . ? O2 P1 O4 103.42(13) . . ? O3 P1 O4 101.76(13) . . ? O6 P2 O5 117.23(13) . . ? O6 P2 O8 107.61(12) . . ? O5 P2 O8 110.06(13) . . ? O6 P2 O7 111.87(13) . . ? O5 P2 O7 103.64(12) . . ? O8 P2 O7 105.86(12) . . ? P1 O1 Cu1 125.25(13) . . ? C13 O3 P1 126.0(2) . . ? C17 O4 P1 127.23(19) . . ? P2 O5 Cu1 128.14(13) . . ? C21 O7 P2 126.59(19) . . ? C25 O8 P2 128.55(19) . . ? Cu1 O9 H9A 107(3) . . ? Cu1 O9 H9B 103(3) . . ? H9A O9 H9B 102(4) . . ? C1 N1 C5 118.1(3) . . ? C1 N1 Cu1 127.7(2) . . ? C5 N1 Cu1 114.1(2) . . ? C12 N2 C6 118.0(3) . . ? C12 N2 Cu1 129.5(2) . . ? C6 N2 Cu1 112.5(2) . . ? N1 C1 C2 122.0(3) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 117.2(3) . . ? C5 C4 C9 118.3(3) . . ? C3 C4 C9 124.5(3) . . ? N1 C5 C4 123.4(3) . . ? N1 C5 C6 116.1(3) . . ? C4 C5 C6 120.5(3) . . ? N2 C6 C7 123.9(3) . . ? N2 C6 C5 116.4(3) . . ? C7 C6 C5 119.7(3) . . ? C6 C7 C10 116.4(3) . . ? C6 C7 C8 118.8(3) . . ? C10 C7 C8 124.9(3) . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C4 121.6(3) . . ? C8 C9 H9 119.2 . . ? C4 C9 H9 119.2 . . ? C11 C10 C7 119.9(3) . . ? C11 C10 H10 120.0 . . ? C7 C10 H10 120.0 . . ? C10 C11 C12 119.4(3) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N2 C12 C11 122.5(3) . . ? N2 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? O3 C13 C14 108.5(3) . . ? O3 C13 C15 110.8(3) . . ? C14 C13 C15 112.7(4) . . ? O3 C13 C16 104.1(3) . . ? C14 C13 C16 109.6(4) . . ? C15 C13 C16 110.8(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 C20 110.8(3) . . ? O4 C17 C19 103.5(3) . . ? C20 C17 C19 110.9(4) . . ? O4 C17 C18 108.8(3) . . ? C20 C17 C18 111.4(3) . . ? C19 C17 C18 111.1(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O7 C21 C24 103.5(3) . . ? O7 C21 C23 111.5(3) . . ? C24 C21 C23 111.3(4) . . ? O7 C21 C22 108.2(3) . . ? C24 C21 C22 110.6(3) . . ? C23 C21 C22 111.4(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 C28 104.7(3) . . ? O8 C25 C26 112.0(3) . . ? C28 C25 C26 110.3(3) . . ? O8 C25 C27 107.9(3) . . ? C28 C25 C27 110.3(3) . . ? C26 C25 C27 111.5(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O9 H9A O2 0.92(5) 1.71(5) 2.599(3) 162(4) . O9 H9B O6 0.81(5) 1.88(5) 2.658(3) 163(4) . _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.829 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.091 ##==END data_93K_structure_of_2 _database_code_CSD 211841 _chemical_name_common cu-phenanthroline-dtbp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H46 Cu N2 O9 P2' _chemical_formula_weight 680.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.5402(8) _cell_length_b 17.5622(12) _cell_length_c 17.3494(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.2700(10) _cell_angle_gamma 90.00 _cell_volume 3198.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1436 _exptl_absorpt_coefficient_mu 0.836 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0 _exptl_absorpt_correction_T_max 0 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24146 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 29.06 _reflns_number_total 7993 _reflns_number_gt 6736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution SHELXS-97 _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^)+(0.0255P)^2^+5.3986P] 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 7993 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 0.77521(3) 0.887340(17) 0.573281(17) 0.01021(8) Uani 1 1 d . . . P1 P 0.95421(6) 0.75899(4) 0.50259(4) 0.01098(13) Uani 1 1 d . . . P2 P 0.89883(6) 0.91631(4) 0.74217(4) 0.01099(13) Uani 1 1 d . . . O1 O 0.83625(16) 0.77530(10) 0.54230(10) 0.0123(4) Uani 1 1 d . . . O2 O 1.01852(17) 0.82678(10) 0.47059(10) 0.0149(4) Uani 1 1 d . . . O3 O 0.92654(17) 0.69474(11) 0.43833(10) 0.0151(4) Uani 1 1 d . . . O4 O 1.06313(16) 0.71896(10) 0.55866(10) 0.0139(4) Uani 1 1 d . . . O5 O 0.79120(17) 0.88558(11) 0.68678(10) 0.0139(4) Uani 1 1 d . . . O6 O 1.02920(17) 0.91590(10) 0.71507(10) 0.0142(4) Uani 1 1 d . . . O7 O 0.85309(17) 1.00034(10) 0.76075(10) 0.0135(4) Uani 1 1 d . . . O8 O 0.90549(17) 0.87083(10) 0.82118(10) 0.0136(4) Uani 1 1 d . . . O9 O 0.94769(18) 0.93031(11) 0.56559(12) 0.0143(4) Uani 1 1 d . . . N1 N 0.5887(2) 0.86207(12) 0.57228(12) 0.0121(4) Uani 1 1 d . . . N2 N 0.7124(2) 0.93286(12) 0.46789(12) 0.0122(4) Uani 1 1 d . . . C1 C 0.5305(3) 0.82549(14) 0.62590(16) 0.0153(5) Uani 1 1 d . . . H1 H 0.5796 0.8085 0.6713 0.018 Uiso 1 1 calc R . . C2 C 0.3989(3) 0.81090(16) 0.61791(17) 0.0183(5) Uani 1 1 d . . . H2 H 0.3607 0.7836 0.6570 0.022 Uiso 1 1 calc R . . C3 C 0.3253(3) 0.83634(16) 0.55317(16) 0.0184(6) Uani 1 1 d . . . H3 H 0.2362 0.8269 0.5473 0.022 Uiso 1 1 calc R . . C4 C 0.3843(2) 0.87635(14) 0.49619(15) 0.0137(5) Uani 1 1 d . . . C5 C 0.5170(2) 0.88684(14) 0.50815(14) 0.0120(5) Uani 1 1 d . . . C6 C 0.5837(2) 0.92563(13) 0.45176(14) 0.0117(5) Uani 1 1 d . . . C7 C 0.5168(2) 0.95436(14) 0.38410(15) 0.0144(5) Uani 1 1 d . . . C8 C 0.3803(3) 0.94435(15) 0.37360(16) 0.0175(5) Uani 1 1 d . . . H8 H 0.3338 0.9641 0.3285 0.021 Uiso 1 1 calc R . . C9 C 0.3178(3) 0.90724(15) 0.42697(16) 0.0179(6) Uani 1 1 d . . . H9 H 0.2280 0.9014 0.4186 0.021 Uiso 1 1 calc R . . C10 C 0.5889(3) 0.99144(15) 0.33118(15) 0.0169(5) Uani 1 1 d . . . H10 H 0.5482 1.0115 0.2844 0.020 Uiso 1 1 calc R . . C11 C 0.7187(3) 0.99868(15) 0.34734(16) 0.0172(5) Uani 1 1 d . . . H11 H 0.7680 1.0241 0.3120 0.021 Uiso 1 1 calc R . . C12 C 0.7778(3) 0.96812(14) 0.41676(15) 0.0144(5) Uani 1 1 d . . . H12 H 0.8675 0.9730 0.4272 0.017 Uiso 1 1 calc R . . C13 C 0.8066(2) 0.68528(16) 0.38861(15) 0.0170(5) Uani 1 1 d . . . C14 C 0.7087(3) 0.64651(18) 0.43416(18) 0.0251(6) Uani 1 1 d . . . H14A H 0.6924 0.6781 0.4787 0.038 Uiso 1 1 calc R . . H14B H 0.7412 0.5968 0.4523 0.038 Uiso 1 1 calc R . . H14C H 0.6293 0.6396 0.4009 0.038 Uiso 1 1 calc R . . C15 C 0.7578(3) 0.76147(18) 0.35702(18) 0.0290(7) Uani 1 1 d . . . H15A H 0.8255 0.7874 0.3321 0.043 Uiso 1 1 calc R . . H15B H 0.7320 0.7929 0.3995 0.043 Uiso 1 1 calc R . . H15C H 0.6845 0.7532 0.3190 0.043 Uiso 1 1 calc R . . C16 C 0.8423(3) 0.6338(2) 0.32384(18) 0.0310(7) Uani 1 1 d . . . H16A H 0.9073 0.6588 0.2958 0.047 Uiso 1 1 calc R . . H16B H 0.7667 0.6236 0.2882 0.047 Uiso 1 1 calc R . . H16C H 0.8761 0.5857 0.3457 0.047 Uiso 1 1 calc R . . C17 C 1.0461(3) 0.66231(15) 0.61888(16) 0.0168(5) Uani 1 1 d . . . C18 C 0.9841(3) 0.70019(17) 0.68463(16) 0.0230(6) Uani 1 1 d . . . H18A H 1.0328 0.7457 0.7016 0.034 Uiso 1 1 calc R . . H18B H 0.9830 0.6645 0.7280 0.034 Uiso 1 1 calc R . . H18C H 0.8966 0.7148 0.6667 0.034 Uiso 1 1 calc R . . C19 C 1.1811(3) 0.6374(2) 0.6453(2) 0.0311(8) Uani 1 1 d . . . H19A H 1.2303 0.6813 0.6661 0.047 Uiso 1 1 calc R . . H19B H 1.2213 0.6163 0.6012 0.047 Uiso 1 1 calc R . . H19C H 1.1789 0.5984 0.6856 0.047 Uiso 1 1 calc R . . C20 C 0.9700(3) 0.59460(16) 0.58507(18) 0.0232(6) Uani 1 1 d . . . H20A H 0.8837 0.6112 0.5668 0.035 Uiso 1 1 calc R . . H20B H 0.9655 0.5555 0.6250 0.035 Uiso 1 1 calc R . . H20C H 1.0118 0.5735 0.5416 0.035 Uiso 1 1 calc R . . C21 C 0.9321(3) 1.06137(14) 0.79809(15) 0.0149(5) Uani 1 1 d . . . C22 C 1.0047(3) 1.09976(16) 0.73747(16) 0.0200(6) Uiso 1 1 d . . . H22A H 0.9444 1.1188 0.6955 0.030 Uiso 1 1 calc R . . H22B H 1.0625 1.0629 0.7166 0.030 Uiso 1 1 calc R . . H22C H 1.0541 1.1424 0.7610 0.030 Uiso 1 1 calc R . . C23 C 1.0219(3) 1.03082(17) 0.86498(17) 0.0232(6) Uani 1 1 d . . . H23A H 1.0857 0.9976 0.8446 0.035 Uiso 1 1 calc R . . H23B H 0.9730 1.0017 0.9003 0.035 Uiso 1 1 calc R . . H23C H 1.0647 1.0735 0.8930 0.035 Uiso 1 1 calc R . . C24 C 0.8358(3) 1.11556(17) 0.8279(2) 0.0297(7) Uani 1 1 d . . . H24A H 0.7883 1.0893 0.8659 0.044 Uiso 1 1 calc R . . H24B H 0.7766 1.1329 0.7846 0.044 Uiso 1 1 calc R . . H24C H 0.8803 1.1595 0.8523 0.044 Uiso 1 1 calc R . . C25 C 0.7985(3) 0.84504(15) 0.86380(15) 0.0153(5) Uani 1 1 d . . . C26 C 0.6927(3) 0.90393(16) 0.86201(18) 0.0223(6) Uani 1 1 d . . . H26A H 0.6572 0.9120 0.8084 0.033 Uiso 1 1 calc R . . H26B H 0.7272 0.9520 0.8836 0.033 Uiso 1 1 calc R . . H26C H 0.6255 0.8858 0.8929 0.033 Uiso 1 1 calc R . . C27 C 0.7509(3) 0.76982(16) 0.82920(17) 0.0235(6) Uani 1 1 d . . . H27A H 0.7162 0.7778 0.7755 0.035 Uiso 1 1 calc R . . H27B H 0.6841 0.7496 0.8592 0.035 Uiso 1 1 calc R . . H27C H 0.8217 0.7335 0.8306 0.035 Uiso 1 1 calc R . . C28 C 0.8584(3) 0.83383(18) 0.94634(16) 0.0237(6) Uani 1 1 d . . . H28A H 0.8916 0.8826 0.9669 0.036 Uiso 1 1 calc R . . H28B H 0.9282 0.7970 0.9464 0.036 Uiso 1 1 calc R . . H28C H 0.7939 0.8148 0.9787 0.036 Uiso 1 1 calc R . . H9A H 0.988(4) 0.899(2) 0.534(2) 0.036(10) Uiso 1 1 d . . . H9B H 0.979(4) 0.927(2) 0.608(2) 0.041(12) 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 0.00630(14) 0.01194(14) 0.01176(14) 0.00061(11) -0.00264(10) -0.00155(12) P1 0.0070(3) 0.0130(3) 0.0124(3) -0.0005(2) -0.0021(2) -0.0009(2) P2 0.0084(3) 0.0124(3) 0.0116(3) 0.0006(2) -0.0026(2) -0.0006(2) O1 0.0087(8) 0.0134(8) 0.0145(8) -0.0013(7) -0.0011(7) -0.0005(7) O2 0.0104(9) 0.0171(9) 0.0168(9) 0.0017(7) -0.0006(7) -0.0023(7) O3 0.0090(8) 0.0193(9) 0.0160(9) -0.0058(7) -0.0036(7) -0.0001(7) O4 0.0071(8) 0.0171(9) 0.0168(9) 0.0033(7) -0.0037(7) -0.0016(7) O5 0.0107(8) 0.0189(9) 0.0117(8) -0.0010(7) -0.0021(7) -0.0055(7) O6 0.0104(9) 0.0166(9) 0.0153(9) 0.0002(7) -0.0011(7) 0.0000(7) O7 0.0081(8) 0.0117(8) 0.0197(9) -0.0009(7) -0.0038(7) 0.0001(7) O8 0.0120(9) 0.0154(9) 0.0131(8) 0.0030(7) -0.0010(7) 0.0004(7) O9 0.0110(9) 0.0164(9) 0.0151(9) 0.0008(7) -0.0014(8) -0.0024(7) N1 0.0104(10) 0.0094(9) 0.0162(10) -0.0012(8) -0.0008(8) -0.0001(8) N2 0.0095(10) 0.0112(10) 0.0153(10) -0.0005(8) -0.0016(8) 0.0017(8) C1 0.0133(12) 0.0131(12) 0.0190(13) -0.0006(10) -0.0019(10) -0.0016(10) C2 0.0133(13) 0.0171(13) 0.0247(14) -0.0008(10) 0.0037(11) -0.0049(10) C3 0.0093(12) 0.0181(13) 0.0274(15) -0.0070(11) -0.0013(11) -0.0025(10) C4 0.0091(11) 0.0113(12) 0.0202(13) -0.0065(9) -0.0018(10) 0.0007(9) C5 0.0097(11) 0.0112(11) 0.0144(11) -0.0034(9) -0.0027(9) -0.0001(9) C6 0.0108(12) 0.0080(11) 0.0157(12) -0.0034(9) -0.0024(9) 0.0026(9) C7 0.0126(12) 0.0137(12) 0.0161(12) -0.0041(9) -0.0037(10) 0.0034(10) C8 0.0160(13) 0.0152(12) 0.0195(13) -0.0052(10) -0.0074(10) 0.0033(10) C9 0.0114(12) 0.0159(12) 0.0248(14) -0.0095(10) -0.0065(11) 0.0024(10) C10 0.0216(14) 0.0150(12) 0.0131(12) -0.0006(9) -0.0036(10) 0.0042(11) C11 0.0188(13) 0.0171(12) 0.0157(12) 0.0005(10) 0.0016(10) 0.0020(11) C12 0.0118(12) 0.0141(12) 0.0170(12) -0.0018(9) 0.0004(10) -0.0005(10) C13 0.0095(12) 0.0231(14) 0.0171(13) -0.0066(10) -0.0064(10) -0.0010(10) C14 0.0153(14) 0.0322(16) 0.0266(15) -0.0059(12) -0.0045(12) -0.0064(12) C15 0.0311(17) 0.0269(16) 0.0260(15) 0.0027(12) -0.0139(13) 0.0013(13) C16 0.0234(16) 0.0441(19) 0.0238(15) -0.0157(14) -0.0071(13) 0.0024(14) C17 0.0115(12) 0.0169(12) 0.0213(13) 0.0072(10) -0.0034(10) -0.0003(10) C18 0.0247(15) 0.0262(15) 0.0175(13) 0.0027(11) -0.0008(11) -0.0033(12) C19 0.0125(14) 0.0408(18) 0.0386(18) 0.0236(15) -0.0058(13) 0.0010(13) C20 0.0236(15) 0.0161(13) 0.0296(15) 0.0024(11) 0.0008(12) -0.0051(11) C21 0.0138(12) 0.0113(11) 0.0191(12) -0.0027(9) -0.0009(10) -0.0041(10) C23 0.0241(15) 0.0224(14) 0.0211(14) 0.0008(11) -0.0082(12) -0.0088(12) C24 0.0253(16) 0.0177(14) 0.048(2) -0.0085(13) 0.0121(14) -0.0031(13) C25 0.0137(12) 0.0157(12) 0.0167(12) 0.0036(10) 0.0017(10) -0.0022(10) C26 0.0149(13) 0.0192(14) 0.0337(16) 0.0039(11) 0.0074(12) 0.0009(11) C27 0.0269(16) 0.0166(13) 0.0264(15) 0.0023(11) -0.0005(12) -0.0068(12) C28 0.0239(15) 0.0304(16) 0.0165(13) 0.0065(11) -0.0003(11) -0.0069(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 Cu1 O5 1.9611(17) . ? Cu1 O9 1.9842(19) . ? Cu1 N1 2.014(2) . ? Cu1 N2 2.049(2) . ? Cu1 O1 2.1537(18) . ? P1 O2 1.5015(19) . ? P1 O1 1.5032(19) . ? P1 O3 1.5943(19) . ? P1 O4 1.5979(18) . ? P2 O6 1.4926(19) . ? P2 O5 1.5170(18) . ? P2 O8 1.5825(18) . ? P2 O7 1.5947(19) . ? O3 C13 1.473(3) . ? O4 C17 1.466(3) . ? O7 C21 1.471(3) . ? O8 C25 1.475(3) . ? O9 H9A 0.92(4) . ? O9 H9B 0.78(4) . ? N1 C1 1.326(3) . ? N1 C5 1.358(3) . ? N2 C12 1.326(3) . ? N2 C6 1.366(3) . ? C1 C2 1.405(4) . ? C1 H1 0.9500 . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? C3 C4 1.403(4) . ? C3 H3 0.9500 . ? C4 C5 1.408(3) . ? C4 C9 1.440(4) . ? C5 C6 1.429(4) . ? C6 C7 1.406(3) . ? C7 C10 1.405(4) . ? C7 C8 1.444(4) . ? C8 C9 1.353(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.377(4) . ? C10 H10 0.9500 . ? C11 C12 1.410(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C16 1.517(4) . ? C13 C14 1.517(4) . ? C13 C15 1.518(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.519(4) . ? C17 C18 1.519(4) . ? C17 C20 1.522(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.515(4) . ? C21 C24 1.516(4) . ? C21 C23 1.526(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C27 1.517(4) . ? C25 C26 1.519(4) . ? C25 C28 1.524(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? 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 O5 Cu1 O9 94.52(8) . . ? O5 Cu1 N1 89.94(8) . . ? O9 Cu1 N1 169.41(8) . . ? O5 Cu1 N2 153.27(8) . . ? O9 Cu1 N2 90.82(8) . . ? N1 Cu1 N2 80.99(9) . . ? O5 Cu1 O1 103.66(7) . . ? O9 Cu1 O1 91.95(7) . . ? N1 Cu1 O1 96.33(8) . . ? N2 Cu1 O1 102.31(8) . . ? O2 P1 O1 116.03(11) . . ? O2 P1 O3 111.25(11) . . ? O1 P1 O3 110.46(10) . . ? O2 P1 O4 104.50(10) . . ? O1 P1 O4 112.53(10) . . ? O3 P1 O4 100.92(10) . . ? O6 P2 O5 117.09(11) . . ? O6 P2 O8 107.55(10) . . ? O5 P2 O8 109.89(10) . . ? O6 P2 O7 111.85(10) . . ? O5 P2 O7 103.58(10) . . ? O8 P2 O7 106.38(10) . . ? P1 O1 Cu1 124.55(10) . . ? C13 O3 P1 125.55(16) . . ? C17 O4 P1 127.19(16) . . ? P2 O5 Cu1 128.37(11) . . ? C21 O7 P2 126.45(16) . . ? C25 O8 P2 127.87(16) . . ? Cu1 O9 H9A 107(2) . . ? Cu1 O9 H9B 103(3) . . ? H9A O9 H9B 109(4) . . ? C1 N1 C5 118.1(2) . . ? C1 N1 Cu1 127.93(18) . . ? C5 N1 Cu1 113.93(17) . . ? C12 N2 C6 118.3(2) . . ? C12 N2 Cu1 129.37(18) . . ? C6 N2 Cu1 112.32(17) . . ? N1 C1 C2 122.4(2) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 118.9(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 117.4(2) . . ? C3 C4 C9 124.3(2) . . ? C5 C4 C9 118.3(2) . . ? N1 C5 C4 123.3(2) . . ? N1 C5 C6 116.3(2) . . ? C4 C5 C6 120.4(2) . . ? N2 C6 C7 123.4(2) . . ? N2 C6 C5 116.5(2) . . ? C7 C6 C5 120.2(2) . . ? C10 C7 C6 116.9(2) . . ? C10 C7 C8 124.5(2) . . ? C6 C7 C8 118.6(2) . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C4 121.5(2) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? C11 C10 C7 119.8(2) . . ? C11 C10 H10 120.1 . . ? C7 C10 H10 120.1 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N2 C12 C11 122.2(2) . . ? N2 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? O3 C13 C16 104.0(2) . . ? O3 C13 C14 109.5(2) . . ? C16 C13 C14 110.2(2) . . ? O3 C13 C15 110.9(2) . . ? C16 C13 C15 110.9(3) . . ? C14 C13 C15 111.1(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 C19 103.8(2) . . ? O4 C17 C18 109.1(2) . . ? C19 C17 C18 110.8(2) . . ? O4 C17 C20 110.5(2) . . ? C19 C17 C20 109.7(2) . . ? C18 C17 C20 112.6(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O7 C21 C22 108.7(2) . . ? O7 C21 C24 103.8(2) . . ? C22 C21 C24 110.7(2) . . ? O7 C21 C23 111.4(2) . . ? C22 C21 C23 111.5(2) . . ? C24 C21 C23 110.5(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 C27 108.0(2) . . ? O8 C25 C26 112.0(2) . . ? C27 C25 C26 111.7(2) . . ? O8 C25 C28 103.9(2) . . ? C27 C25 C28 110.6(2) . . ? C26 C25 C28 110.3(2) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O2 P1 O1 Cu1 -11.32(16) . . . . ? O3 P1 O1 Cu1 -139.11(11) . . . . ? O4 P1 O1 Cu1 108.96(12) . . . . ? O5 Cu1 O1 P1 -113.94(12) . . . . ? O9 Cu1 O1 P1 -18.82(13) . . . . ? N1 Cu1 O1 P1 154.57(13) . . . . ? N2 Cu1 O1 P1 72.45(13) . . . . ? O2 P1 O3 C13 -94.1(2) . . . . ? O1 P1 O3 C13 36.2(2) . . . . ? O4 P1 O3 C13 155.5(2) . . . . ? O2 P1 O4 C17 163.5(2) . . . . ? O1 P1 O4 C17 36.8(2) . . . . ? O3 P1 O4 C17 -81.0(2) . . . . ? O6 P2 O5 Cu1 -30.39(19) . . . . ? O8 P2 O5 Cu1 -153.44(13) . . . . ? O7 P2 O5 Cu1 93.23(15) . . . . ? O9 Cu1 O5 P2 5.44(15) . . . . ? N1 Cu1 O5 P2 -164.95(15) . . . . ? N2 Cu1 O5 P2 -95.4(2) . . . . ? O1 Cu1 O5 P2 98.55(15) . . . . ? O6 P2 O7 C21 -39.1(2) . . . . ? O5 P2 O7 C21 -166.10(19) . . . . ? O8 P2 O7 C21 78.1(2) . . . . ? O6 P2 O8 C25 -169.25(19) . . . . ? O5 P2 O8 C25 -40.8(2) . . . . ? O7 P2 O8 C25 70.8(2) . . . . ? O5 Cu1 N1 C1 -26.0(2) . . . . ? O9 Cu1 N1 C1 -141.1(4) . . . . ? N2 Cu1 N1 C1 179.2(2) . . . . ? O1 Cu1 N1 C1 77.7(2) . . . . ? O5 Cu1 N1 C5 153.55(18) . . . . ? O9 Cu1 N1 C5 38.5(6) . . . . ? N2 Cu1 N1 C5 -1.21(17) . . . . ? O1 Cu1 N1 C5 -102.71(17) . . . . ? O5 Cu1 N2 C12 108.6(3) . . . . ? O9 Cu1 N2 C12 6.8(2) . . . . ? N1 Cu1 N2 C12 -179.9(2) . . . . ? O1 Cu1 N2 C12 -85.4(2) . . . . ? O5 Cu1 N2 C6 -69.9(3) . . . . ? O9 Cu1 N2 C6 -171.66(17) . . . . ? N1 Cu1 N2 C6 1.59(16) . . . . ? O1 Cu1 N2 C6 96.16(17) . . . . ? C5 N1 C1 C2 0.9(4) . . . . ? Cu1 N1 C1 C2 -179.54(19) . . . . ? N1 C1 C2 C3 -1.3(4) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 C9 -178.6(2) . . . . ? C1 N1 C5 C4 0.7(4) . . . . ? Cu1 N1 C5 C4 -178.94(19) . . . . ? C1 N1 C5 C6 -179.7(2) . . . . ? Cu1 N1 C5 C6 0.6(3) . . . . ? C3 C4 C5 N1 -1.8(4) . . . . ? C9 C4 C5 N1 178.1(2) . . . . ? C3 C4 C5 C6 178.7(2) . . . . ? C9 C4 C5 C6 -1.5(4) . . . . ? C12 N2 C6 C7 -0.7(4) . . . . ? Cu1 N2 C6 C7 177.98(19) . . . . ? C12 N2 C6 C5 179.6(2) . . . . ? Cu1 N2 C6 C5 -1.7(3) . . . . ? N1 C5 C6 N2 0.8(3) . . . . ? C4 C5 C6 N2 -179.6(2) . . . . ? N1 C5 C6 C7 -179.0(2) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? N2 C6 C7 C10 0.6(4) . . . . ? C5 C6 C7 C10 -179.7(2) . . . . ? N2 C6 C7 C8 -179.1(2) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C10 C7 C8 C9 179.3(3) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? C3 C4 C9 C8 -179.0(3) . . . . ? C5 C4 C9 C8 1.2(4) . . . . ? C6 C7 C10 C11 -0.5(4) . . . . ? C8 C7 C10 C11 179.2(3) . . . . ? C7 C10 C11 C12 0.5(4) . . . . ? C6 N2 C12 C11 0.6(4) . . . . ? Cu1 N2 C12 C11 -177.76(19) . . . . ? C10 C11 C12 N2 -0.6(4) . . . . ? P1 O3 C13 C16 163.6(2) . . . . ? P1 O3 C13 C14 -78.6(3) . . . . ? P1 O3 C13 C15 44.3(3) . . . . ? P1 O4 C17 C19 172.7(2) . . . . ? P1 O4 C17 C18 -69.1(3) . . . . ? P1 O4 C17 C20 55.1(3) . . . . ? P2 O7 C21 C22 82.4(2) . . . . ? P2 O7 C21 C24 -159.7(2) . . . . ? P2 O7 C21 C23 -40.8(3) . . . . ? P2 O8 C25 C27 83.9(2) . . . . ? P2 O8 C25 C26 -39.5(3) . . . . ? P2 O8 C25 C28 -158.54(19) . . . . ? 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 H9A O2 0.92(4) 1.72(4) 2.609(3) 162(4) . O9 H9B O6 0.78(4) 1.90(4) 2.668(3) 171(4) . _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.687 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.085