data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Vickie McKee' _publ_contact_author_address ; Chemistry Department Loughborough University Loughborough LE11 3TU UK ; _publ_contact_author_email v.mckee@lboro.ac.uk _publ_section_title ; Bis-Phenanthroline Copper(II) Phthalate Complexes are Potent in vitro Antitumour Agents with 'Self-Activating' Metallo-Nuclease and DNA Binding Properties ; _publ_author_name 'Vickie McKee' # Attachment '- complex 4.cif' data_x82656_0m _database_code_depnum_ccdc_archive 'CCDC 783510' #TrackingRef '- complex 4.cif' _audit_update_record ; 2009-03-10 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H20 Cu N4 O4, 2(C2 H6 O), 3(H2 O)' _chemical_formula_sum 'C36 H38 Cu N4 O9' _chemical_formula_weight 734.24 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.335(6) _cell_length_b 12.183(6) _cell_length_c 14.539(7) _cell_angle_alpha 113.97(2) _cell_angle_beta 92.95(3) _cell_angle_gamma 108.81(3) _cell_volume 1697.5(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7702 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 30.23 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 766 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6731 _exptl_absorpt_correction_T_max 0.7753 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33406 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 32.44 _reflns_number_total 10772 _reflns_number_gt 8566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0443P)^2^+0.6519P] 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 10772 _refine_ls_number_parameters 473 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.032 _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 0.129907(18) 0.265930(17) 0.253368(13) 0.01145(5) Uani 1 1 d . . . N11 N 0.23938(13) 0.27101(12) 0.14984(9) 0.0129(2) Uani 1 1 d . . . N12 N -0.01809(13) 0.15668(12) 0.11024(9) 0.0127(2) Uani 1 1 d . . . N21 N 0.09484(12) 0.43029(12) 0.27125(9) 0.0130(2) Uani 1 1 d . . . N22 N 0.00233(12) 0.25792(12) 0.34291(9) 0.0118(2) Uani 1 1 d . . . O1 O 0.20886(10) 0.17055(10) 0.30380(8) 0.0117(2) Uani 1 1 d . . . O2 O 0.31988(11) 0.37919(10) 0.39781(8) 0.0159(2) Uani 1 1 d . . . O3 O 0.22737(11) -0.08730(10) 0.29226(8) 0.0163(2) Uani 1 1 d . . . O4 O 0.11380(11) -0.00992(11) 0.40693(8) 0.0165(2) Uani 1 1 d . . . C1 C 0.29534(14) 0.26471(14) 0.37974(11) 0.0112(3) Uani 1 1 d . . . C2 C 0.36814(14) 0.23362(13) 0.44851(11) 0.0110(3) Uani 1 1 d . . . C3 C 0.33393(14) 0.11024(14) 0.44325(10) 0.0108(3) Uani 1 1 d . . . C4 C 0.40677(15) 0.09074(15) 0.51102(11) 0.0141(3) Uani 1 1 d . . . H4 H 0.3844 0.0066 0.5072 0.017 Uiso 1 1 calc R . . C5 C 0.51114(16) 0.19203(15) 0.58375(11) 0.0164(3) Uani 1 1 d . . . H5 H 0.5600 0.1777 0.6297 0.020 Uiso 1 1 calc R . . C6 C 0.54389(15) 0.31445(15) 0.58907(11) 0.0163(3) Uani 1 1 d . . . H6 H 0.6151 0.3847 0.6392 0.020 Uiso 1 1 calc R . . C7 C 0.47326(15) 0.33471(14) 0.52165(11) 0.0140(3) Uani 1 1 d . . . H7 H 0.4969 0.4189 0.5254 0.017 Uiso 1 1 calc R . . C8 C 0.21579(15) -0.00421(14) 0.37334(11) 0.0126(3) Uani 1 1 d . . . C111 C 0.36608(15) 0.32189(15) 0.16989(12) 0.0168(3) Uani 1 1 d . . . H111 H 0.4109 0.3588 0.2390 0.020 Uiso 1 1 calc R . . C112 C 0.43691(17) 0.32359(16) 0.09325(13) 0.0203(3) Uani 1 1 d . . . H112 H 0.5275 0.3594 0.1104 0.024 Uiso 1 1 calc R . . C113 C 0.37349(17) 0.27299(16) -0.00602(13) 0.0196(3) Uani 1 1 d . . . H113 H 0.4195 0.2737 -0.0587 0.023 Uiso 1 1 calc R . . C114 C 0.23906(16) 0.21966(15) -0.02966(12) 0.0158(3) Uani 1 1 d . . . C115 C 0.16538(17) 0.16723(15) -0.13093(12) 0.0179(3) Uani 1 1 d . . . H115 H 0.2073 0.1671 -0.1859 0.022 Uiso 1 1 calc R . . C116 C 0.03594(17) 0.11755(15) -0.14954(11) 0.0175(3) Uani 1 1 d . . . H116 H -0.0112 0.0855 -0.2171 0.021 Uiso 1 1 calc R . . C117 C -0.03136(16) 0.11249(14) -0.06900(11) 0.0141(3) Uani 1 1 d . . . C118 C -0.16563(16) 0.05838(14) -0.08485(12) 0.0168(3) Uani 1 1 d . . . H118 H -0.2170 0.0244 -0.1512 0.020 Uiso 1 1 calc R . . C119 C -0.22169(16) 0.05520(15) -0.00348(12) 0.0175(3) Uani 1 1 d . . . H119 H -0.3119 0.0196 -0.0130 0.021 Uiso 1 1 calc R . . C120 C -0.14422(15) 0.10487(14) 0.09288(12) 0.0150(3) Uani 1 1 d . . . H120 H -0.1834 0.1015 0.1484 0.018 Uiso 1 1 calc R . . C121 C 0.03827(15) 0.16182(13) 0.03077(11) 0.0125(3) Uani 1 1 d . . . C122 C 0.17539(15) 0.21917(14) 0.05110(11) 0.0133(3) Uani 1 1 d . . . C211 C 0.14662(16) 0.51818(14) 0.23802(12) 0.0167(3) Uani 1 1 d . . . H211 H 0.2142 0.5122 0.2027 0.020 Uiso 1 1 calc R . . C212 C 0.10445(18) 0.61947(15) 0.25355(13) 0.0212(3) Uani 1 1 d . . . H212 H 0.1443 0.6819 0.2302 0.025 Uiso 1 1 calc R . . C213 C 0.00485(18) 0.62782(15) 0.30288(12) 0.0220(4) Uani 1 1 d . . . H213 H -0.0249 0.6955 0.3127 0.026 Uiso 1 1 calc R . . C214 C -0.05321(17) 0.53579(15) 0.33887(12) 0.0176(3) Uani 1 1 d . . . C215 C -0.15559(18) 0.53774(16) 0.39322(13) 0.0220(4) Uani 1 1 d . . . H215 H -0.1908 0.6018 0.4036 0.026 Uiso 1 1 calc R . . C216 C -0.20317(17) 0.44966(17) 0.43020(13) 0.0211(3) Uani 1 1 d . . . H216 H -0.2705 0.4531 0.4662 0.025 Uiso 1 1 calc R . . C217 C -0.15163(15) 0.35166(15) 0.41475(11) 0.0158(3) Uani 1 1 d . . . C218 C -0.19373(16) 0.25891(16) 0.45293(12) 0.0190(3) Uani 1 1 d . . . H218 H -0.2606 0.2578 0.4897 0.023 Uiso 1 1 calc R . . C219 C -0.13671(16) 0.17039(16) 0.43618(12) 0.0188(3) Uani 1 1 d . . . H219 H -0.1635 0.1081 0.4619 0.023 Uiso 1 1 calc R . . C220 C -0.03841(15) 0.17259(14) 0.38070(11) 0.0145(3) Uani 1 1 d . . . H220 H 0.0003 0.1110 0.3698 0.017 Uiso 1 1 calc R . . C221 C -0.05300(15) 0.34657(14) 0.36038(11) 0.0126(3) Uani 1 1 d . . . C222 C -0.00262(15) 0.43978(14) 0.32158(11) 0.0139(3) Uani 1 1 d . . . C1S C 0.5354(2) 0.0920(2) 0.21166(17) 0.0374(5) Uani 1 1 d . . . H1S1 H 0.5285 0.0521 0.1369 0.056 Uiso 1 1 calc R . . H1S2 H 0.6142 0.1692 0.2445 0.056 Uiso 1 1 calc R . . H1S3 H 0.4621 0.1168 0.2274 0.056 Uiso 1 1 calc R . . C2S C 0.53753(18) -0.00333(19) 0.25173(14) 0.0268(4) Uani 1 1 d . . . H2S1 H 0.6127 -0.0268 0.2368 0.032 Uiso 1 1 calc R . . H2S2 H 0.5463 0.0380 0.3274 0.032 Uiso 1 1 calc R . . O1S O 0.42513(12) -0.11789(12) 0.20683(10) 0.0255(3) Uani 1 1 d . . . H1S H 0.3653 -0.1031 0.2347 0.038 Uiso 1 1 calc R . . C3S C 0.8253(3) 0.3774(2) 0.0416(2) 0.0608(9) Uani 1 1 d . . . H3S1 H 0.8011 0.3753 0.1048 0.091 Uiso 1 1 calc R . . H3S2 H 0.9105 0.3744 0.0395 0.091 Uiso 1 1 calc R . . H3S3 H 0.7637 0.3025 -0.0184 0.091 Uiso 1 1 calc R . . C4S C 0.82615(18) 0.49914(18) 0.03985(14) 0.0260(4) Uani 1 1 d . . . H4S1 H 0.8893 0.5747 0.0999 0.031 Uiso 1 1 calc R . . H4S2 H 0.8522 0.5019 -0.0234 0.031 Uiso 1 1 calc R . . O2S O 0.70353(13) 0.50726(13) 0.04263(10) 0.0265(3) Uani 1 1 d . . . H2S H 0.6589 0.4674 -0.0174 0.040 Uiso 1 1 calc R . . O1W O 0.85843(12) 0.84862(12) 0.38175(9) 0.0227(3) Uani 1 1 d D . . H11W H 0.855(2) 0.884(2) 0.4445(12) 0.027 Uiso 1 1 d D . . H12W H 0.9365(15) 0.881(2) 0.3787(16) 0.027 Uiso 1 1 d D . . O2W O 0.41797(13) 0.63434(13) 0.15944(10) 0.0252(3) Uani 1 1 d D . . H21W H 0.4914(17) 0.635(2) 0.1814(17) 0.030 Uiso 1 1 d D . . H22W H 0.423(2) 0.7118(16) 0.1737(17) 0.030 Uiso 1 1 d D . . O3W O 0.65031(15) 0.63060(14) 0.23157(10) 0.0325(3) Uani 1 1 d D . . H31W H 0.677(2) 0.606(2) 0.1776(14) 0.039 Uiso 1 1 d D . . H32W H 0.705(2) 0.6982(18) 0.2805(15) 0.039 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 0.01236(10) 0.01317(9) 0.01124(9) 0.00686(7) 0.00293(6) 0.00584(7) N11 0.0141(6) 0.0133(6) 0.0124(6) 0.0067(5) 0.0022(5) 0.0052(5) N12 0.0152(7) 0.0113(5) 0.0120(5) 0.0053(4) 0.0034(5) 0.0052(5) N21 0.0130(6) 0.0117(5) 0.0121(5) 0.0050(4) -0.0011(5) 0.0029(5) N22 0.0127(6) 0.0108(5) 0.0106(5) 0.0037(4) 0.0011(4) 0.0046(5) O1 0.0124(5) 0.0106(4) 0.0104(4) 0.0039(4) -0.0002(4) 0.0037(4) O2 0.0183(6) 0.0104(5) 0.0167(5) 0.0052(4) -0.0008(4) 0.0045(4) O3 0.0185(6) 0.0111(5) 0.0157(5) 0.0036(4) 0.0010(4) 0.0048(4) O4 0.0129(6) 0.0170(5) 0.0166(5) 0.0076(4) 0.0026(4) 0.0019(4) C1 0.0107(7) 0.0130(6) 0.0105(6) 0.0054(5) 0.0034(5) 0.0048(5) C2 0.0111(7) 0.0109(6) 0.0109(6) 0.0046(5) 0.0025(5) 0.0044(5) C3 0.0099(7) 0.0121(6) 0.0096(6) 0.0042(5) 0.0023(5) 0.0040(5) C4 0.0154(8) 0.0149(7) 0.0136(6) 0.0071(5) 0.0035(5) 0.0067(6) C5 0.0164(8) 0.0209(7) 0.0127(7) 0.0075(6) 0.0008(6) 0.0084(6) C6 0.0131(8) 0.0175(7) 0.0129(7) 0.0039(5) -0.0017(5) 0.0034(6) C7 0.0140(7) 0.0115(6) 0.0134(6) 0.0041(5) 0.0008(5) 0.0032(5) C8 0.0152(7) 0.0106(6) 0.0124(6) 0.0070(5) 0.0002(5) 0.0032(5) C111 0.0141(8) 0.0183(7) 0.0175(7) 0.0091(6) 0.0018(6) 0.0043(6) C112 0.0151(8) 0.0226(8) 0.0237(8) 0.0122(7) 0.0056(6) 0.0051(6) C113 0.0210(9) 0.0195(7) 0.0197(7) 0.0107(6) 0.0094(6) 0.0063(6) C114 0.0208(8) 0.0144(7) 0.0143(7) 0.0081(6) 0.0060(6) 0.0067(6) C115 0.0252(9) 0.0172(7) 0.0130(7) 0.0074(6) 0.0066(6) 0.0088(6) C116 0.0278(9) 0.0152(7) 0.0101(6) 0.0058(5) 0.0032(6) 0.0086(6) C117 0.0200(8) 0.0102(6) 0.0116(6) 0.0042(5) 0.0013(6) 0.0064(6) C118 0.0203(8) 0.0131(7) 0.0137(7) 0.0039(5) -0.0018(6) 0.0059(6) C119 0.0151(8) 0.0148(7) 0.0181(7) 0.0050(6) -0.0006(6) 0.0040(6) C120 0.0152(8) 0.0133(6) 0.0142(7) 0.0051(5) 0.0029(6) 0.0040(6) C121 0.0158(7) 0.0099(6) 0.0114(6) 0.0043(5) 0.0016(5) 0.0051(5) C122 0.0168(8) 0.0119(6) 0.0128(6) 0.0066(5) 0.0034(5) 0.0059(6) C211 0.0175(8) 0.0135(7) 0.0152(7) 0.0066(5) -0.0027(6) 0.0018(6) C212 0.0291(10) 0.0117(7) 0.0190(7) 0.0079(6) -0.0035(7) 0.0033(6) C213 0.0329(10) 0.0128(7) 0.0181(7) 0.0041(6) -0.0031(7) 0.0106(7) C214 0.0232(9) 0.0143(7) 0.0133(7) 0.0027(5) -0.0018(6) 0.0098(6) C215 0.0263(9) 0.0208(8) 0.0189(8) 0.0036(6) 0.0019(7) 0.0162(7) C216 0.0203(9) 0.0248(8) 0.0168(7) 0.0036(6) 0.0043(6) 0.0141(7) C217 0.0146(8) 0.0162(7) 0.0120(6) 0.0021(5) 0.0009(5) 0.0060(6) C218 0.0163(8) 0.0220(8) 0.0164(7) 0.0064(6) 0.0059(6) 0.0068(6) C219 0.0191(8) 0.0190(7) 0.0178(7) 0.0097(6) 0.0054(6) 0.0045(6) C220 0.0159(8) 0.0137(6) 0.0139(7) 0.0061(5) 0.0024(6) 0.0055(6) C221 0.0119(7) 0.0126(6) 0.0098(6) 0.0023(5) -0.0010(5) 0.0044(5) C222 0.0163(8) 0.0108(6) 0.0106(6) 0.0020(5) -0.0015(5) 0.0044(5) C1S 0.0285(11) 0.0390(11) 0.0386(11) 0.0208(9) 0.0012(9) 0.0019(9) C2S 0.0179(9) 0.0328(10) 0.0253(9) 0.0110(7) 0.0012(7) 0.0072(7) O1S 0.0212(7) 0.0239(6) 0.0274(6) 0.0070(5) 0.0053(5) 0.0095(5) C3S 0.0504(16) 0.0234(10) 0.0812(19) 0.0010(11) -0.0326(14) 0.0170(10) C4S 0.0240(10) 0.0291(9) 0.0203(8) 0.0071(7) 0.0004(7) 0.0105(7) O2S 0.0264(7) 0.0265(6) 0.0214(6) 0.0036(5) -0.0009(5) 0.0138(6) O1W 0.0143(6) 0.0210(6) 0.0192(6) 0.0003(5) 0.0037(5) 0.0013(5) O2W 0.0257(7) 0.0238(6) 0.0218(6) 0.0076(5) 0.0063(5) 0.0075(5) O3W 0.0354(9) 0.0271(7) 0.0182(6) 0.0039(5) 0.0009(6) 0.0002(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 O1 1.9961(12) . ? Cu1 N22 2.0004(15) . ? Cu1 N11 2.0069(15) . ? Cu1 N21 2.0824(16) . ? Cu1 N12 2.2060(17) . ? N11 C111 1.330(2) . ? N11 C122 1.359(2) . ? N12 C120 1.326(2) . ? N12 C121 1.362(2) . ? N21 C211 1.330(2) . ? N21 C222 1.366(2) . ? N22 C220 1.333(2) . ? N22 C221 1.362(2) . ? O1 C1 1.2768(18) . ? O2 C1 1.2394(19) . ? O3 C8 1.2504(19) . ? O4 C8 1.270(2) . ? C1 C2 1.500(2) . ? C2 C7 1.388(2) . ? C2 C3 1.394(2) . ? C3 C4 1.394(2) . ? C3 C8 1.508(2) . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 C7 1.381(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C111 C112 1.409(2) . ? C111 H111 0.9500 . ? C112 C113 1.365(2) . ? C112 H112 0.9500 . ? C113 C114 1.410(3) . ? C113 H113 0.9500 . ? C114 C122 1.411(2) . ? C114 C115 1.428(2) . ? C115 C116 1.359(3) . ? C115 H115 0.9500 . ? C116 C117 1.441(2) . ? C116 H116 0.9500 . ? C117 C121 1.399(2) . ? C117 C118 1.413(2) . ? C118 C119 1.380(2) . ? C118 H118 0.9500 . ? C119 C120 1.394(2) . ? C119 H119 0.9500 . ? C120 H120 0.9500 . ? C121 C122 1.441(2) . ? C211 C212 1.403(2) . ? C211 H211 0.9500 . ? C212 C213 1.377(3) . ? C212 H212 0.9500 . ? C213 C214 1.414(2) . ? C213 H213 0.9500 . ? C214 C222 1.403(2) . ? C214 C215 1.438(3) . ? C215 C216 1.363(3) . ? C215 H215 0.9500 . ? C216 C217 1.436(2) . ? C216 H216 0.9500 . ? C217 C221 1.405(2) . ? C217 C218 1.415(2) . ? C218 C219 1.376(2) . ? C218 H218 0.9500 . ? C219 C220 1.408(2) . ? C219 H219 0.9500 . ? C220 H220 0.9500 . ? C221 C222 1.439(2) . ? C1S C2S 1.501(3) . ? C1S H1S1 0.9800 . ? C1S H1S2 0.9800 . ? C1S H1S3 0.9800 . ? C2S O1S 1.423(2) . ? C2S H2S1 0.9900 . ? C2S H2S2 0.9900 . ? O1S H1S 0.8400 . ? C3S C4S 1.490(3) . ? C3S H3S1 0.9800 . ? C3S H3S2 0.9800 . ? C3S H3S3 0.9800 . ? C4S O2S 1.426(2) . ? C4S H4S1 0.9900 . ? C4S H4S2 0.9900 . ? O2S H2S 0.8400 . ? O1W H11W 0.844(15) . ? O1W H12W 0.857(15) . ? O2W H21W 0.873(15) . ? O2W H22W 0.859(15) . ? O3W H31W 0.831(15) . ? O3W H32W 0.849(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N22 91.46(6) . . ? O1 Cu1 N11 94.65(6) . . ? N22 Cu1 N11 172.44(5) . . ? O1 Cu1 N21 152.58(5) . . ? N22 Cu1 N21 81.21(6) . . ? N11 Cu1 N21 95.26(6) . . ? O1 Cu1 N12 119.26(5) . . ? N22 Cu1 N12 93.21(6) . . ? N11 Cu1 N12 79.91(6) . . ? N21 Cu1 N12 87.67(6) . . ? C111 N11 C122 118.46(14) . . ? C111 N11 Cu1 126.03(11) . . ? C122 N11 Cu1 115.50(11) . . ? C120 N12 C121 118.76(13) . . ? C120 N12 Cu1 132.18(11) . . ? C121 N12 Cu1 108.51(10) . . ? C211 N21 C222 118.39(14) . . ? C211 N21 Cu1 130.69(12) . . ? C222 N21 Cu1 110.82(10) . . ? C220 N22 C221 118.04(14) . . ? C220 N22 Cu1 127.65(11) . . ? C221 N22 Cu1 114.18(10) . . ? C1 O1 Cu1 100.90(10) . . ? O2 C1 O1 122.14(14) . . ? O2 C1 C2 119.84(13) . . ? O1 C1 C2 118.02(13) . . ? C7 C2 C3 119.39(14) . . ? C7 C2 C1 117.30(13) . . ? C3 C2 C1 123.30(13) . . ? C4 C3 C2 119.25(14) . . ? C4 C3 C8 116.45(13) . . ? C2 C3 C8 124.14(13) . . ? C5 C4 C3 120.96(14) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.46(14) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 120.12(15) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 120.81(14) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O3 C8 O4 126.16(14) . . ? O3 C8 C3 118.35(14) . . ? O4 C8 C3 115.34(13) . . ? N11 C111 C112 122.96(15) . . ? N11 C111 H111 118.5 . . ? C112 C111 H111 118.5 . . ? C113 C112 C111 119.03(16) . . ? C113 C112 H112 120.5 . . ? C111 C112 H112 120.5 . . ? C112 C113 C114 119.41(15) . . ? C112 C113 H113 120.3 . . ? C114 C113 H113 120.3 . . ? C113 C114 C122 118.02(14) . . ? C113 C114 C115 123.01(15) . . ? C122 C114 C115 118.97(15) . . ? C116 C115 C114 120.69(15) . . ? C116 C115 H115 119.7 . . ? C114 C115 H115 119.7 . . ? C115 C116 C117 121.42(14) . . ? C115 C116 H116 119.3 . . ? C117 C116 H116 119.3 . . ? C121 C117 C118 117.13(14) . . ? C121 C117 C116 119.17(15) . . ? C118 C117 C116 123.69(14) . . ? C119 C118 C117 119.64(14) . . ? C119 C118 H118 120.2 . . ? C117 C118 H118 120.2 . . ? C118 C119 C120 119.08(16) . . ? C118 C119 H119 120.5 . . ? C120 C119 H119 120.5 . . ? N12 C120 C119 122.68(15) . . ? N12 C120 H120 118.7 . . ? C119 C120 H120 118.7 . . ? N12 C121 C117 122.70(15) . . ? N12 C121 C122 118.06(13) . . ? C117 C121 C122 119.24(14) . . ? N11 C122 C114 122.09(15) . . ? N11 C122 C121 117.49(14) . . ? C114 C122 C121 120.42(14) . . ? N21 C211 C212 121.99(17) . . ? N21 C211 H211 119.0 . . ? C212 C211 H211 119.0 . . ? C213 C212 C211 119.59(15) . . ? C213 C212 H212 120.2 . . ? C211 C212 H212 120.2 . . ? C212 C213 C214 120.11(15) . . ? C212 C213 H213 119.9 . . ? C214 C213 H213 119.9 . . ? C222 C214 C213 116.07(16) . . ? C222 C214 C215 119.52(15) . . ? C213 C214 C215 124.39(15) . . ? C216 C215 C214 121.41(15) . . ? C216 C215 H215 119.3 . . ? C214 C215 H215 119.3 . . ? C215 C216 C217 120.06(16) . . ? C215 C216 H216 120.0 . . ? C217 C216 H216 120.0 . . ? C221 C217 C218 117.07(15) . . ? C221 C217 C216 119.52(15) . . ? C218 C217 C216 123.41(16) . . ? C219 C218 C217 119.27(16) . . ? C219 C218 H218 120.4 . . ? C217 C218 H218 120.4 . . ? C218 C219 C220 119.69(15) . . ? C218 C219 H219 120.2 . . ? C220 C219 H219 120.2 . . ? N22 C220 C219 122.38(15) . . ? N22 C220 H220 118.8 . . ? C219 C220 H220 118.8 . . ? N22 C221 C217 123.55(14) . . ? N22 C221 C222 116.06(14) . . ? C217 C221 C222 120.38(14) . . ? N21 C222 C214 123.83(15) . . ? N21 C222 C221 117.05(14) . . ? C214 C222 C221 119.10(15) . . ? C2S C1S H1S1 109.5 . . ? C2S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? C2S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? O1S C2S C1S 112.12(16) . . ? O1S C2S H2S1 109.2 . . ? C1S C2S H2S1 109.2 . . ? O1S C2S H2S2 109.2 . . ? C1S C2S H2S2 109.2 . . ? H2S1 C2S H2S2 107.9 . . ? C2S O1S H1S 109.5 . . ? C4S C3S H3S1 109.5 . . ? C4S C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? C4S C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? O2S C4S C3S 111.29(19) . . ? O2S C4S H4S1 109.4 . . ? C3S C4S H4S1 109.4 . . ? O2S C4S H4S2 109.4 . . ? C3S C4S H4S2 109.4 . . ? H4S1 C4S H4S2 108.0 . . ? C4S O2S H2S 109.5 . . ? H11W O1W H12W 106.1(19) . . ? H21W O2W H22W 110(2) . . ? H31W O3W H32W 113(2) . . ? 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 O1 Cu1 N11 C111 -57.49(13) . . . . ? N21 Cu1 N11 C111 96.91(13) . . . . ? N12 Cu1 N11 C111 -176.41(13) . . . . ? O1 Cu1 N11 C122 123.85(11) . . . . ? N21 Cu1 N11 C122 -81.75(11) . . . . ? N12 Cu1 N11 C122 4.93(10) . . . . ? O1 Cu1 N12 C120 92.73(14) . . . . ? N22 Cu1 N12 C120 -0.74(14) . . . . ? N11 Cu1 N12 C120 -177.57(14) . . . . ? N21 Cu1 N12 C120 -81.80(14) . . . . ? O1 Cu1 N12 C121 -96.12(10) . . . . ? N22 Cu1 N12 C121 170.40(10) . . . . ? N11 Cu1 N12 C121 -6.43(9) . . . . ? N21 Cu1 N12 C121 89.34(10) . . . . ? O1 Cu1 N21 C211 100.75(16) . . . . ? N22 Cu1 N21 C211 176.75(14) . . . . ? N11 Cu1 N21 C211 -10.00(14) . . . . ? N12 Cu1 N21 C211 -89.64(14) . . . . ? O1 Cu1 N21 C222 -82.87(15) . . . . ? N22 Cu1 N21 C222 -6.87(10) . . . . ? N11 Cu1 N21 C222 166.39(10) . . . . ? N12 Cu1 N21 C222 86.74(11) . . . . ? O1 Cu1 N22 C220 -23.76(13) . . . . ? N21 Cu1 N22 C220 -177.21(13) . . . . ? N12 Cu1 N22 C220 95.65(13) . . . . ? O1 Cu1 N22 C221 160.59(10) . . . . ? N21 Cu1 N22 C221 7.14(10) . . . . ? N12 Cu1 N22 C221 -79.99(11) . . . . ? N22 Cu1 O1 C1 -91.39(10) . . . . ? N11 Cu1 O1 C1 93.07(10) . . . . ? N21 Cu1 O1 C1 -17.81(15) . . . . ? N12 Cu1 O1 C1 174.11(9) . . . . ? Cu1 O1 C1 O2 -7.35(16) . . . . ? Cu1 O1 C1 C2 172.46(11) . . . . ? O2 C1 C2 C7 -9.0(2) . . . . ? O1 C1 C2 C7 171.17(13) . . . . ? O2 C1 C2 C3 169.86(14) . . . . ? O1 C1 C2 C3 -10.0(2) . . . . ? C7 C2 C3 C4 -0.6(2) . . . . ? C1 C2 C3 C4 -179.43(14) . . . . ? C7 C2 C3 C8 174.67(14) . . . . ? C1 C2 C3 C8 -4.2(2) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C8 C3 C4 C5 -174.88(14) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 C7 -0.5(2) . . . . ? C5 C6 C7 C2 0.6(2) . . . . ? C3 C2 C7 C6 -0.1(2) . . . . ? C1 C2 C7 C6 178.83(14) . . . . ? C4 C3 C8 O3 -82.87(18) . . . . ? C2 C3 C8 O3 101.76(18) . . . . ? C4 C3 C8 O4 93.07(17) . . . . ? C2 C3 C8 O4 -82.30(18) . . . . ? C122 N11 C111 C112 -0.5(2) . . . . ? Cu1 N11 C111 C112 -179.12(12) . . . . ? N11 C111 C112 C113 1.2(3) . . . . ? C111 C112 C113 C114 -0.4(2) . . . . ? C112 C113 C114 C122 -1.0(2) . . . . ? C112 C113 C114 C115 178.68(16) . . . . ? C113 C114 C115 C116 -179.65(15) . . . . ? C122 C114 C115 C116 0.0(2) . . . . ? C114 C115 C116 C117 -1.8(2) . . . . ? C115 C116 C117 C121 1.1(2) . . . . ? C115 C116 C117 C118 -178.05(15) . . . . ? C121 C117 C118 C119 -0.6(2) . . . . ? C116 C117 C118 C119 178.56(14) . . . . ? C117 C118 C119 C120 -0.4(2) . . . . ? C121 N12 C120 C119 0.1(2) . . . . ? Cu1 N12 C120 C119 170.49(11) . . . . ? C118 C119 C120 N12 0.7(2) . . . . ? C120 N12 C121 C117 -1.2(2) . . . . ? Cu1 N12 C121 C117 -173.72(11) . . . . ? C120 N12 C121 C122 179.62(13) . . . . ? Cu1 N12 C121 C122 7.09(15) . . . . ? C118 C117 C121 N12 1.4(2) . . . . ? C116 C117 C121 N12 -177.75(13) . . . . ? C118 C117 C121 C122 -179.39(13) . . . . ? C116 C117 C121 C122 1.4(2) . . . . ? C111 N11 C122 C114 -1.0(2) . . . . ? Cu1 N11 C122 C114 177.79(11) . . . . ? C111 N11 C122 C121 178.55(13) . . . . ? Cu1 N11 C122 C121 -2.68(17) . . . . ? C113 C114 C122 N11 1.7(2) . . . . ? C115 C114 C122 N11 -177.96(14) . . . . ? C113 C114 C122 C121 -177.81(14) . . . . ? C115 C114 C122 C121 2.5(2) . . . . ? N12 C121 C122 N11 -3.6(2) . . . . ? C117 C121 C122 N11 177.23(13) . . . . ? N12 C121 C122 C114 175.99(13) . . . . ? C117 C121 C122 C114 -3.2(2) . . . . ? C222 N21 C211 C212 0.3(2) . . . . ? Cu1 N21 C211 C212 176.41(11) . . . . ? N21 C211 C212 C213 -1.3(2) . . . . ? C211 C212 C213 C214 0.9(2) . . . . ? C212 C213 C214 C222 0.4(2) . . . . ? C212 C213 C214 C215 178.52(15) . . . . ? C222 C214 C215 C216 1.3(2) . . . . ? C213 C214 C215 C216 -176.78(16) . . . . ? C214 C215 C216 C217 -0.4(3) . . . . ? C215 C216 C217 C221 -0.7(2) . . . . ? C215 C216 C217 C218 178.40(16) . . . . ? C221 C217 C218 C219 0.5(2) . . . . ? C216 C217 C218 C219 -178.61(15) . . . . ? C217 C218 C219 C220 -0.6(2) . . . . ? C221 N22 C220 C219 0.9(2) . . . . ? Cu1 N22 C220 C219 -174.64(11) . . . . ? C218 C219 C220 N22 -0.1(2) . . . . ? C220 N22 C221 C217 -0.9(2) . . . . ? Cu1 N22 C221 C217 175.19(11) . . . . ? C220 N22 C221 C222 177.69(13) . . . . ? Cu1 N22 C221 C222 -6.22(16) . . . . ? C218 C217 C221 N22 0.2(2) . . . . ? C216 C217 C221 N22 179.38(14) . . . . ? C218 C217 C221 C222 -178.31(14) . . . . ? C216 C217 C221 C222 0.8(2) . . . . ? C211 N21 C222 C214 1.2(2) . . . . ? Cu1 N21 C222 C214 -175.71(12) . . . . ? C211 N21 C222 C221 -177.45(13) . . . . ? Cu1 N21 C222 C221 5.67(16) . . . . ? C213 C214 C222 N21 -1.5(2) . . . . ? C215 C214 C222 N21 -179.69(14) . . . . ? C213 C214 C222 C221 177.11(14) . . . . ? C215 C214 C222 C221 -1.1(2) . . . . ? N22 C221 C222 N21 0.11(19) . . . . ? C217 C221 C222 N21 178.75(13) . . . . ? N22 C221 C222 C214 -178.58(13) . . . . ? C217 C221 C222 C214 0.1(2) . . . . ? 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 O1S H1S O3 0.84 1.84 2.675(2) 174.5 . O2S H2S O2W 0.84 1.90 2.727(2) 169.6 2_665 O1W H11W O4 0.844(15) 2.007(16) 2.828(2) 164(2) 2_666 O1W H12W O4 0.857(15) 1.928(16) 2.765(2) 165(2) 1_665 O2W H21W O3W 0.873(15) 1.933(15) 2.805(3) 178(2) . O2W H22W O1S 0.859(15) 1.924(15) 2.782(2) 176(2) 1_565 O3W H31W O2S 0.831(15) 1.938(16) 2.751(2) 165(2) . O3W H32W O1W 0.849(16) 2.008(16) 2.847(2) 170(2) . _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.595 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.072 # Attachment '- complex 5.cif' data_x80561 _database_code_depnum_ccdc_archive 'CCDC 783511' #TrackingRef '- complex 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34.50 H38 Cu N4 O10.50' _chemical_formula_weight 740.23 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' 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 10.9068(7) _cell_length_b 11.8165(8) _cell_length_c 14.7457(10) _cell_angle_alpha 74.650(4) _cell_angle_beta 79.904(3) _cell_angle_gamma 68.909(2) _cell_volume 1703.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3012 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 32.38 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8375 _exptl_absorpt_correction_T_max 0.9014 _exptl_absorpt_process_details 'Sheldrick, 2002; 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 53727 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28.39 _reflns_number_total 8301 _reflns_number_gt 7310 _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^)+(0.0818P)^2^+1.5614P] 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 8301 _refine_ls_number_parameters 500 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.007 _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 0.87067(2) 0.715370(19) 0.734518(15) 0.01753(8) Uani 1 1 d . . . N1 N 0.99101(15) 0.77559(14) 0.62986(11) 0.0191(3) Uani 1 1 d . . . N2 N 0.83276(15) 0.65024(14) 0.63118(11) 0.0190(3) Uani 1 1 d . . . N3 N 0.73767(16) 0.66488(14) 0.83487(11) 0.0192(3) Uani 1 1 d . . . N4 N 0.99710(17) 0.53367(15) 0.81211(12) 0.0214(3) Uani 1 1 d . . . C11 C 0.78751(18) 0.93592(17) 0.77554(13) 0.0190(3) Uani 1 1 d . . . O11 O 0.87654(13) 0.83375(12) 0.80761(10) 0.0208(3) Uani 1 1 d . . . C12 C 0.77675(19) 1.04836(17) 0.80961(13) 0.0198(3) Uani 1 1 d . . . O12 O 0.71221(14) 0.94603(12) 0.71726(10) 0.0227(3) Uani 1 1 d . . . C13 C 0.67532(18) 1.15940(16) 0.78073(13) 0.0189(3) Uani 1 1 d . . . H13 H 0.6126 1.1613 0.7425 0.023 Uiso 1 1 calc R . . C14 C 0.66516(19) 1.26724(17) 0.80731(13) 0.0205(4) Uani 1 1 d . . . C15 C 0.7575(2) 1.26275(19) 0.86385(16) 0.0282(4) Uani 1 1 d . . . H15 H 0.7516 1.3358 0.8824 0.034 Uiso 1 1 calc R . . C16 C 0.8579(3) 1.1526(2) 0.89320(18) 0.0362(5) Uani 1 1 d . . . H16 H 0.9195 1.1505 0.9323 0.043 Uiso 1 1 calc R . . C17 C 0.8690(2) 1.04503(19) 0.86588(16) 0.0291(4) Uani 1 1 d . . . H17 H 0.9387 0.9700 0.8853 0.035 Uiso 1 1 calc R . . C18 C 0.55775(19) 1.38845(17) 0.77252(13) 0.0206(4) Uani 1 1 d . . . O19 O 0.55657(15) 1.48366(12) 0.79607(10) 0.0252(3) Uani 1 1 d . . . O20 O 0.47729(15) 1.38473(14) 0.72261(11) 0.0294(3) Uani 1 1 d . . . C112 C 1.06789(19) 0.84027(17) 0.63206(15) 0.0224(4) Uani 1 1 d . . . H112 H 1.0722 0.8585 0.6902 0.027 Uiso 1 1 calc R . . C113 C 1.14254(19) 0.88220(18) 0.55167(15) 0.0246(4) Uani 1 1 d . . . H113 H 1.1954 0.9292 0.5555 0.030 Uiso 1 1 calc R . . C114 C 1.13936(19) 0.85537(18) 0.46691(15) 0.0243(4) Uani 1 1 d . . . H114 H 1.1905 0.8827 0.4121 0.029 Uiso 1 1 calc R . . C115 C 1.05883(18) 0.78657(18) 0.46275(14) 0.0224(4) Uani 1 1 d . . . C116 C 1.0459(2) 0.7542(2) 0.37835(14) 0.0264(4) Uani 1 1 d . . . H116 H 1.0942 0.7790 0.3210 0.032 Uiso 1 1 calc R . . C117 C 0.9655(2) 0.6887(2) 0.37954(14) 0.0268(4) Uani 1 1 d . . . H117 H 0.9592 0.6679 0.3229 0.032 Uiso 1 1 calc R . . C118 C 0.89007(19) 0.65025(18) 0.46414(14) 0.0229(4) Uani 1 1 d . . . C119 C 0.8036(2) 0.58282(19) 0.47057(15) 0.0261(4) Uani 1 1 d . . . H119 H 0.7920 0.5600 0.4163 0.031 Uiso 1 1 calc R . . C120 C 0.7364(2) 0.5506(2) 0.55593(16) 0.0270(4) Uani 1 1 d . . . H120 H 0.6791 0.5043 0.5612 0.032 Uiso 1 1 calc R . . C121 C 0.75281(19) 0.58636(18) 0.63522(14) 0.0226(4) Uani 1 1 d . . . H121 H 0.7052 0.5642 0.6937 0.027 Uiso 1 1 calc R . . C122 C 0.90075(18) 0.68072(16) 0.54755(13) 0.0190(3) Uani 1 1 d . . . C123 C 0.98670(18) 0.74925(16) 0.54637(13) 0.0191(3) Uani 1 1 d . . . C211 C 0.6108(2) 0.73229(18) 0.84512(14) 0.0238(4) Uani 1 1 d . . . H211 H 0.5757 0.8034 0.7971 0.029 Uiso 1 1 calc R . . C212 C 0.5269(2) 0.7019(2) 0.92449(16) 0.0285(4) Uani 1 1 d . . . H212 H 0.4369 0.7524 0.9304 0.034 Uiso 1 1 calc R . . C213 C 0.5767(2) 0.5983(2) 0.99337(15) 0.0284(4) Uani 1 1 d . . . H213 H 0.5215 0.5769 1.0477 0.034 Uiso 1 1 calc R . . C214 C 0.7095(2) 0.52398(19) 0.98339(14) 0.0253(4) Uani 1 1 d . . . C215 C 0.7677(3) 0.4127(2) 1.05174(15) 0.0303(5) Uani 1 1 d . . . H215 H 0.7152 0.3869 1.1063 0.036 Uiso 1 1 calc R . . C216 C 0.8966(3) 0.3445(2) 1.03892(15) 0.0332(5) Uani 1 1 d . . . H216 H 0.9332 0.2714 1.0849 0.040 Uiso 1 1 calc R . . C217 C 0.9791(2) 0.38037(18) 0.95721(15) 0.0267(4) Uani 1 1 d . . . C218 C 1.1134(2) 0.3130(2) 0.94028(17) 0.0333(5) Uani 1 1 d . . . H218 H 1.1543 0.2382 0.9834 0.040 Uiso 1 1 calc R . . C219 C 1.1854(2) 0.3560(2) 0.86079(19) 0.0338(5) Uani 1 1 d . . . H219 H 1.2755 0.3101 0.8479 0.041 Uiso 1 1 calc R . . C220 C 1.1240(2) 0.46844(19) 0.79894(16) 0.0271(4) Uani 1 1 d . . . H220 H 1.1754 0.4990 0.7456 0.033 Uiso 1 1 calc R . . C221 C 0.9250(2) 0.49038(17) 0.88923(13) 0.0211(4) Uani 1 1 d . . . C222 C 0.7875(2) 0.56115(17) 0.90234(13) 0.0208(4) Uani 1 1 d . . . C1S C 0.3382(4) 1.0560(5) 0.7134(4) 0.0953(17) Uani 1 1 d . . . H1S1 H 0.3071 1.1439 0.6812 0.143 Uiso 1 1 calc R A . H1S2 H 0.3892 1.0059 0.6676 0.143 Uiso 1 1 calc R . . H1S3 H 0.3942 1.0451 0.7624 0.143 Uiso 1 1 calc R . . C2S C 0.2271(5) 1.0169(4) 0.7560(5) 0.0644(14) Uani 0.75 1 d P A -1 H2S1 H 0.1708 1.0784 0.7933 0.077 Uiso 0.75 1 calc PR A -1 H2S2 H 0.1760 1.0254 0.7039 0.077 Uiso 0.75 1 calc PR A -1 C2T C 0.2365(14) 0.9943(17) 0.8112(8) 0.059(3) Uani 0.25 1 d PU A -2 H2T1 H 0.2643 0.9964 0.8710 0.071 Uiso 0.25 1 calc PR A -2 H2T2 H 0.1438 1.0497 0.8066 0.071 Uiso 0.25 1 calc PR A -2 O1S O 0.2408(5) 0.8991(3) 0.8144(2) 0.1289(17) Uani 1 1 d U . . H1S H 0.2760 0.8446 0.7823 0.193 Uiso 1 1 calc R A . O1W O 0.67485(17) 0.94243(16) 0.53606(12) 0.0349(4) Uani 1 1 d D . . H11W H 0.683(3) 0.946(3) 0.5979(14) 0.042 Uiso 1 1 d D . . H21W H 0.605(2) 0.9138(19) 0.5315(19) 0.042 Uiso 1 1 d D . . O2W O 0.49308(18) 0.82829(16) 0.54445(13) 0.0363(4) Uani 1 1 d D . . H12W H 0.465(3) 0.800(3) 0.6078(13) 0.044 Uiso 1 1 d D . . H22W H 0.4283(18) 0.8948(17) 0.5122(19) 0.044 Uiso 1 1 d D . . O3W O 0.38820(17) 0.71354(14) 0.72045(12) 0.0322(3) Uani 1 1 d D . . H13W H 0.348(3) 0.689(3) 0.6862(18) 0.039 Uiso 1 1 d D . . H23W H 0.447(2) 0.646(2) 0.7480(19) 0.039 Uiso 1 1 d D . . O4W O 0.30932(16) 0.58674(14) 0.61781(12) 0.0312(3) Uani 1 1 d D . . H14W H 0.368(2) 0.518(2) 0.6486(18) 0.037 Uiso 1 1 d D . . H24W H 0.348(3) 0.608(3) 0.5616(14) 0.037 Uiso 1 1 d D . . O5W O 0.5613(2) 0.32261(19) 0.54885(14) 0.0426(4) Uani 1 1 d . . . H15W H 0.529(3) 0.337(3) 0.607(2) 0.051 Uiso 1 1 d D . . H25W H 0.535(3) 0.273(3) 0.543(2) 0.051 Uiso 1 1 d D . . O2S O 0.5369(5) 0.9705(5) 0.0435(5) 0.087(2) Uani 0.50 1 d P B -1 H2S H 0.5379 0.8970 0.0660 0.105 Uiso 0.50 1 calc PR B -1 C3S C 0.6699(5) 0.9775(6) 0.0445(4) 0.0459(12) Uani 0.50 1 d P B -1 H31S H 0.6615 1.0617 0.0479 0.069 Uiso 0.50 1 calc PR B -1 H32S H 0.7241 0.9575 -0.0132 0.069 Uiso 0.50 1 calc PR B -1 H33S H 0.7118 0.9179 0.0996 0.069 Uiso 0.50 1 calc PR B -1 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 0.02051(13) 0.01389(12) 0.01848(13) -0.00310(8) -0.00323(8) -0.00565(9) N1 0.0183(7) 0.0151(7) 0.0228(8) -0.0035(6) -0.0042(6) -0.0037(6) N2 0.0195(7) 0.0172(7) 0.0210(7) -0.0049(6) -0.0029(6) -0.0057(6) N3 0.0243(8) 0.0150(7) 0.0186(7) -0.0037(6) -0.0023(6) -0.0068(6) N4 0.0255(8) 0.0159(7) 0.0244(8) -0.0061(6) -0.0084(6) -0.0048(6) C11 0.0218(8) 0.0157(8) 0.0194(8) -0.0032(6) -0.0026(7) -0.0061(7) O11 0.0234(6) 0.0148(6) 0.0231(7) -0.0037(5) -0.0065(5) -0.0034(5) C12 0.0233(9) 0.0147(8) 0.0217(9) -0.0041(7) -0.0037(7) -0.0056(7) O12 0.0274(7) 0.0170(6) 0.0255(7) -0.0044(5) -0.0092(5) -0.0063(5) C13 0.0214(8) 0.0155(8) 0.0197(8) -0.0040(6) -0.0026(7) -0.0057(7) C14 0.0238(9) 0.0167(8) 0.0197(8) -0.0042(7) 0.0012(7) -0.0063(7) C15 0.0367(11) 0.0190(9) 0.0321(11) -0.0103(8) -0.0090(9) -0.0072(8) C16 0.0431(13) 0.0249(10) 0.0456(13) -0.0124(10) -0.0242(11) -0.0044(9) C17 0.0325(11) 0.0202(9) 0.0356(11) -0.0075(8) -0.0163(9) -0.0028(8) C18 0.0241(9) 0.0149(8) 0.0188(8) -0.0031(6) 0.0029(7) -0.0042(7) O19 0.0324(7) 0.0153(6) 0.0262(7) -0.0058(5) 0.0019(6) -0.0071(5) O20 0.0318(8) 0.0199(7) 0.0336(8) -0.0073(6) -0.0091(6) -0.0012(6) C112 0.0214(9) 0.0167(8) 0.0284(10) -0.0041(7) -0.0057(7) -0.0046(7) C113 0.0190(8) 0.0173(8) 0.0349(11) -0.0018(8) -0.0043(7) -0.0050(7) C114 0.0182(8) 0.0190(9) 0.0300(10) 0.0002(7) 0.0001(7) -0.0046(7) C115 0.0176(8) 0.0191(8) 0.0254(9) -0.0023(7) -0.0023(7) -0.0016(7) C116 0.0240(9) 0.0279(10) 0.0215(9) -0.0034(8) 0.0015(7) -0.0049(8) C117 0.0274(10) 0.0304(10) 0.0208(9) -0.0090(8) -0.0024(7) -0.0048(8) C118 0.0217(9) 0.0228(9) 0.0227(9) -0.0070(7) -0.0038(7) -0.0033(7) C119 0.0280(10) 0.0268(10) 0.0269(10) -0.0105(8) -0.0072(8) -0.0077(8) C120 0.0265(10) 0.0257(10) 0.0339(11) -0.0107(8) -0.0059(8) -0.0102(8) C121 0.0230(9) 0.0204(9) 0.0246(9) -0.0035(7) -0.0021(7) -0.0083(7) C122 0.0182(8) 0.0157(8) 0.0214(8) -0.0032(7) -0.0042(6) -0.0031(6) C123 0.0171(8) 0.0149(8) 0.0228(9) -0.0030(7) -0.0039(7) -0.0023(6) C211 0.0252(9) 0.0202(9) 0.0257(9) -0.0054(7) -0.0018(7) -0.0074(7) C212 0.0288(10) 0.0272(10) 0.0308(10) -0.0121(8) 0.0046(8) -0.0102(8) C213 0.0396(12) 0.0299(10) 0.0220(9) -0.0114(8) 0.0065(8) -0.0189(9) C214 0.0413(11) 0.0237(9) 0.0170(8) -0.0053(7) -0.0040(8) -0.0168(9) C215 0.0527(14) 0.0250(10) 0.0181(9) -0.0012(8) -0.0066(9) -0.0192(10) C216 0.0603(15) 0.0218(9) 0.0220(10) 0.0028(8) -0.0183(10) -0.0177(10) C217 0.0399(11) 0.0175(9) 0.0266(10) -0.0018(7) -0.0180(8) -0.0092(8) C218 0.0411(12) 0.0194(9) 0.0410(12) -0.0014(9) -0.0232(10) -0.0065(9) C219 0.0302(11) 0.0223(10) 0.0505(14) -0.0118(9) -0.0193(10) -0.0005(8) C220 0.0268(10) 0.0230(9) 0.0346(11) -0.0100(8) -0.0102(8) -0.0057(8) C221 0.0302(10) 0.0153(8) 0.0206(9) -0.0037(7) -0.0100(7) -0.0072(7) C222 0.0319(10) 0.0169(8) 0.0168(8) -0.0040(7) -0.0050(7) -0.0103(7) C1S 0.071(3) 0.086(3) 0.126(4) -0.057(3) -0.042(3) 0.018(2) C2S 0.057(3) 0.039(2) 0.091(4) -0.028(2) -0.038(3) 0.0157(19) C2T 0.065(7) 0.090(8) 0.042(6) -0.018(6) -0.017(5) -0.040(6) O1S 0.187(4) 0.0565(17) 0.0680(19) -0.0138(15) 0.028(2) 0.030(2) O1W 0.0335(8) 0.0388(9) 0.0350(9) -0.0060(7) -0.0081(7) -0.0142(7) O2W 0.0405(9) 0.0306(8) 0.0384(9) -0.0008(7) -0.0104(7) -0.0141(7) O3W 0.0342(8) 0.0246(8) 0.0363(9) -0.0039(6) -0.0105(7) -0.0064(6) O4W 0.0279(8) 0.0225(7) 0.0399(9) -0.0045(7) -0.0111(7) -0.0024(6) O5W 0.0484(11) 0.0437(11) 0.0353(9) -0.0161(8) -0.0029(8) -0.0097(8) O2S 0.041(3) 0.063(3) 0.133(6) 0.009(3) 0.005(3) -0.017(2) C3S 0.040(3) 0.054(3) 0.040(3) -0.013(2) 0.003(2) -0.013(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 N1 1.9979(17) . ? Cu1 O11 2.0024(13) . ? Cu1 N3 2.0131(16) . ? Cu1 N2 2.0387(16) . ? Cu1 N4 2.2231(16) . ? N1 C112 1.331(2) . ? N1 C123 1.359(2) . ? N2 C121 1.329(2) . ? N2 C122 1.355(2) . ? N3 C211 1.330(3) . ? N3 C222 1.361(2) . ? N4 C220 1.329(3) . ? N4 C221 1.357(3) . ? C11 O12 1.245(2) . ? C11 O11 1.280(2) . ? C11 C12 1.501(2) . ? C12 C17 1.396(3) . ? C12 C13 1.397(3) . ? C13 C14 1.392(2) . ? C13 H13 0.9500 . ? C14 C15 1.395(3) . ? C14 C18 1.517(3) . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C16 C17 1.391(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 O19 1.258(2) . ? C18 O20 1.259(3) . ? C112 C113 1.398(3) . ? C112 H112 0.9500 . ? C113 C114 1.377(3) . ? C113 H113 0.9500 . ? C114 C115 1.412(3) . ? C114 H114 0.9500 . ? C115 C123 1.398(3) . ? C115 C116 1.438(3) . ? C116 C117 1.358(3) . ? C116 H116 0.9500 . ? C117 C118 1.431(3) . ? C117 H117 0.9500 . ? C118 C122 1.404(3) . ? C118 C119 1.415(3) . ? C119 C120 1.375(3) . ? C119 H119 0.9500 . ? C120 C121 1.403(3) . ? C120 H120 0.9500 . ? C121 H121 0.9500 . ? C122 C123 1.438(3) . ? C211 C212 1.405(3) . ? C211 H211 0.9500 . ? C212 C213 1.372(3) . ? C212 H212 0.9500 . ? C213 C214 1.403(3) . ? C213 H213 0.9500 . ? C214 C222 1.407(3) . ? C214 C215 1.438(3) . ? C215 C216 1.354(4) . ? C215 H215 0.9500 . ? C216 C217 1.437(3) . ? C216 H216 0.9500 . ? C217 C218 1.407(3) . ? C217 C221 1.417(3) . ? C218 C219 1.377(4) . ? C218 H218 0.9500 . ? C219 C220 1.406(3) . ? C219 H219 0.9500 . ? C220 H220 0.9500 . ? C221 C222 1.438(3) . ? C1S C2S 1.435(8) . ? C1S C2T 1.818(9) . ? C1S H1S1 0.9800 . ? C1S H1S2 0.9800 . ? C1S H1S3 0.9800 . ? C2S O1S 1.401(6) . ? C2S H2S1 0.9900 . ? C2S H2S2 0.9900 . ? C2T O1S 1.098(16) . ? C2T H2T1 0.9900 . ? C2T H2T2 0.9900 . ? O1S H1S 0.8400 . ? O1W H11W 0.945(17) . ? O1W H21W 0.960(13) . ? O2W H12W 0.940(17) . ? O2W H22W 0.930(15) . ? O3W H13W 0.886(17) . ? O3W H23W 0.876(17) . ? O4W H14W 0.898(17) . ? O4W H24W 0.880(17) . ? O5W H15W 0.91(3) . ? O5W H25W 0.77(3) . ? O2S C3S 1.486(7) . ? O2S H2S 0.8400 . ? C3S H31S 0.9800 . ? C3S H32S 0.9800 . ? C3S H33S 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 N1 Cu1 O11 90.64(6) . . ? N1 Cu1 N3 175.59(6) . . ? O11 Cu1 N3 89.38(6) . . ? N1 Cu1 N2 81.81(6) . . ? O11 Cu1 N2 160.60(6) . . ? N3 Cu1 N2 96.80(6) . . ? N1 Cu1 N4 105.16(6) . . ? O11 Cu1 N4 102.36(6) . . ? N3 Cu1 N4 79.14(6) . . ? N2 Cu1 N4 96.87(6) . . ? C112 N1 C123 118.26(17) . . ? C112 N1 Cu1 128.19(14) . . ? C123 N1 Cu1 113.49(12) . . ? C121 N2 C122 118.46(16) . . ? C121 N2 Cu1 129.57(14) . . ? C122 N2 Cu1 111.97(12) . . ? C211 N3 C222 119.01(17) . . ? C211 N3 Cu1 124.79(13) . . ? C222 N3 Cu1 115.72(13) . . ? C220 N4 C221 118.31(17) . . ? C220 N4 Cu1 132.55(15) . . ? C221 N4 Cu1 109.05(12) . . ? O12 C11 O11 123.27(17) . . ? O12 C11 C12 119.34(16) . . ? O11 C11 C12 117.38(16) . . ? C11 O11 Cu1 104.37(11) . . ? C17 C12 C13 119.85(17) . . ? C17 C12 C11 121.26(17) . . ? C13 C12 C11 118.83(16) . . ? C14 C13 C12 120.70(17) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 118.97(18) . . ? C13 C14 C18 120.28(17) . . ? C15 C14 C18 120.72(17) . . ? C16 C15 C14 120.53(18) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 119.35(19) . . ? C16 C17 H17 120.3 . . ? C12 C17 H17 120.3 . . ? O19 C18 O20 125.69(18) . . ? O19 C18 C14 117.34(18) . . ? O20 C18 C14 116.96(16) . . ? N1 C112 C113 122.18(19) . . ? N1 C112 H112 118.9 . . ? C113 C112 H112 118.9 . . ? C114 C113 C112 119.96(18) . . ? C114 C113 H113 120.0 . . ? C112 C113 H113 120.0 . . ? C113 C114 C115 118.97(19) . . ? C113 C114 H114 120.5 . . ? C115 C114 H114 120.5 . . ? C123 C115 C114 117.23(18) . . ? C123 C115 C116 118.61(18) . . ? C114 C115 C116 124.16(19) . . ? C117 C116 C115 120.87(19) . . ? C117 C116 H116 119.6 . . ? C115 C116 H116 119.6 . . ? C116 C117 C118 121.50(19) . . ? C116 C117 H117 119.3 . . ? C118 C117 H117 119.3 . . ? C122 C118 C119 116.53(18) . . ? C122 C118 C117 118.81(18) . . ? C119 C118 C117 124.66(18) . . ? C120 C119 C118 119.50(18) . . ? C120 C119 H119 120.2 . . ? C118 C119 H119 120.3 . . ? C119 C120 C121 119.71(19) . . ? C119 C120 H120 120.1 . . ? C121 C120 H120 120.1 . . ? N2 C121 C120 122.11(19) . . ? N2 C121 H121 118.9 . . ? C120 C121 H121 118.9 . . ? N2 C122 C118 123.68(17) . . ? N2 C122 C123 116.67(16) . . ? C118 C122 C123 119.65(18) . . ? N1 C123 C115 123.40(17) . . ? N1 C123 C122 116.03(17) . . ? C115 C123 C122 120.56(17) . . ? N3 C211 C212 122.28(19) . . ? N3 C211 H211 118.9 . . ? C212 C211 H211 118.9 . . ? C213 C212 C211 119.1(2) . . ? C213 C212 H212 120.5 . . ? C211 C212 H212 120.5 . . ? C212 C213 C214 119.86(19) . . ? C212 C213 H213 120.1 . . ? C214 C213 H213 120.1 . . ? C213 C214 C222 117.70(18) . . ? C213 C214 C215 122.9(2) . . ? C222 C214 C215 119.4(2) . . ? C216 C215 C214 120.6(2) . . ? C216 C215 H215 119.7 . . ? C214 C215 H215 119.7 . . ? C215 C216 C217 121.41(19) . . ? C215 C216 H216 119.3 . . ? C217 C216 H216 119.3 . . ? C218 C217 C221 116.9(2) . . ? C218 C217 C216 123.79(19) . . ? C221 C217 C216 119.3(2) . . ? C219 C218 C217 119.7(2) . . ? C219 C218 H218 120.2 . . ? C217 C218 H218 120.2 . . ? C218 C219 C220 119.3(2) . . ? C218 C219 H219 120.3 . . ? C220 C219 H219 120.3 . . ? N4 C220 C219 122.6(2) . . ? N4 C220 H220 118.7 . . ? C219 C220 H220 118.7 . . ? N4 C221 C217 123.15(19) . . ? N4 C221 C222 117.83(16) . . ? C217 C221 C222 119.01(19) . . ? N3 C222 C214 122.07(18) . . ? N3 C222 C221 117.66(17) . . ? C214 C222 C221 120.26(18) . . ? C2S C1S H1S1 109.5 . . ? C2T C1S H1S1 120.2 . . ? C2S C1S H1S2 109.5 . . ? C2T C1S H1S2 120.0 . . ? H1S1 C1S H1S2 109.5 . . ? C2S C1S H1S3 109.5 . . ? C2T C1S H1S3 84.4 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? O1S C2S C1S 122.6(4) . . ? O1S C2S H2S1 106.7 . . ? C1S C2S H2S1 106.7 . . ? O1S C2S H2S2 106.7 . . ? C1S C2S H2S2 106.7 . . ? H2S1 C2S H2S2 106.6 . . ? O1S C2T C1S 114.9(10) . . ? O1S C2T H2T1 108.6 . . ? C1S C2T H2T1 108.6 . . ? O1S C2T H2T2 108.5 . . ? C1S C2T H2T2 108.5 . . ? H2T1 C2T H2T2 107.5 . . ? C2T O1S H1S 138.0 . . ? C2S O1S H1S 109.5 . . ? H11W O1W H21W 114(2) . . ? H12W O2W H22W 113(2) . . ? H13W O3W H23W 105(2) . . ? H14W O4W H24W 106(2) . . ? H15W O5W H25W 106(3) . . ? C3S O2S H2S 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 O11 Cu1 N1 C112 16.86(16) . . . . ? N2 Cu1 N1 C112 178.93(17) . . . . ? N4 Cu1 N1 C112 -86.13(16) . . . . ? O11 Cu1 N1 C123 -160.36(13) . . . . ? N2 Cu1 N1 C123 1.71(12) . . . . ? N4 Cu1 N1 C123 96.65(13) . . . . ? N1 Cu1 N2 C121 179.34(18) . . . . ? O11 Cu1 N2 C121 -112.7(2) . . . . ? N3 Cu1 N2 C121 -4.88(18) . . . . ? N4 Cu1 N2 C121 74.93(17) . . . . ? N1 Cu1 N2 C122 -1.50(12) . . . . ? O11 Cu1 N2 C122 66.5(2) . . . . ? N3 Cu1 N2 C122 174.27(12) . . . . ? N4 Cu1 N2 C122 -105.91(13) . . . . ? O11 Cu1 N3 C211 76.31(16) . . . . ? N2 Cu1 N3 C211 -85.25(16) . . . . ? N4 Cu1 N3 C211 179.02(16) . . . . ? O11 Cu1 N3 C222 -95.67(13) . . . . ? N2 Cu1 N3 C222 102.77(13) . . . . ? N4 Cu1 N3 C222 7.04(12) . . . . ? N1 Cu1 N4 C220 -0.92(19) . . . . ? O11 Cu1 N4 C220 -95.00(18) . . . . ? N3 Cu1 N4 C220 178.06(18) . . . . ? N2 Cu1 N4 C220 82.41(18) . . . . ? N1 Cu1 N4 C221 175.35(12) . . . . ? O11 Cu1 N4 C221 81.26(12) . . . . ? N3 Cu1 N4 C221 -5.68(12) . . . . ? N2 Cu1 N4 C221 -101.32(12) . . . . ? O12 C11 O11 Cu1 5.1(2) . . . . ? C12 C11 O11 Cu1 -173.80(13) . . . . ? N1 Cu1 O11 C11 85.03(12) . . . . ? N3 Cu1 O11 C11 -90.56(13) . . . . ? N2 Cu1 O11 C11 18.5(2) . . . . ? N4 Cu1 O11 C11 -169.30(12) . . . . ? O12 C11 C12 C17 -172.17(19) . . . . ? O11 C11 C12 C17 6.8(3) . . . . ? O12 C11 C12 C13 5.1(3) . . . . ? O11 C11 C12 C13 -175.96(17) . . . . ? C17 C12 C13 C14 0.1(3) . . . . ? C11 C12 C13 C14 -177.19(17) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C12 C13 C14 C18 177.68(17) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C18 C14 C15 C16 -178.1(2) . . . . ? C14 C15 C16 C17 0.7(4) . . . . ? C15 C16 C17 C12 -1.0(4) . . . . ? C13 C12 C17 C16 0.6(3) . . . . ? C11 C12 C17 C16 177.8(2) . . . . ? C13 C14 C18 O19 -177.44(17) . . . . ? C15 C14 C18 O19 0.6(3) . . . . ? C13 C14 C18 O20 2.7(3) . . . . ? C15 C14 C18 O20 -179.29(19) . . . . ? C123 N1 C112 C113 0.5(3) . . . . ? Cu1 N1 C112 C113 -176.57(13) . . . . ? N1 C112 C113 C114 -0.9(3) . . . . ? C112 C113 C114 C115 0.7(3) . . . . ? C113 C114 C115 C123 -0.2(3) . . . . ? C113 C114 C115 C116 179.15(18) . . . . ? C123 C115 C116 C117 -0.1(3) . . . . ? C114 C115 C116 C117 -179.40(19) . . . . ? C115 C116 C117 C118 0.5(3) . . . . ? C116 C117 C118 C122 -0.4(3) . . . . ? C116 C117 C118 C119 179.4(2) . . . . ? C122 C118 C119 C120 -0.3(3) . . . . ? C117 C118 C119 C120 179.82(19) . . . . ? C118 C119 C120 C121 0.9(3) . . . . ? C122 N2 C121 C120 -0.4(3) . . . . ? Cu1 N2 C121 C120 178.73(15) . . . . ? C119 C120 C121 N2 -0.6(3) . . . . ? C121 N2 C122 C118 1.0(3) . . . . ? Cu1 N2 C122 C118 -178.23(15) . . . . ? C121 N2 C122 C123 -179.67(16) . . . . ? Cu1 N2 C122 C123 1.1(2) . . . . ? C119 C118 C122 N2 -0.7(3) . . . . ? C117 C118 C122 N2 179.20(17) . . . . ? C119 C118 C122 C123 -179.95(17) . . . . ? C117 C118 C122 C123 -0.1(3) . . . . ? C112 N1 C123 C115 0.0(3) . . . . ? Cu1 N1 C123 C115 177.53(14) . . . . ? C112 N1 C123 C122 -179.16(16) . . . . ? Cu1 N1 C123 C122 -1.6(2) . . . . ? C114 C115 C123 N1 -0.2(3) . . . . ? C116 C115 C123 N1 -179.55(17) . . . . ? C114 C115 C123 C122 178.95(17) . . . . ? C116 C115 C123 C122 -0.4(3) . . . . ? N2 C122 C123 N1 0.4(2) . . . . ? C118 C122 C123 N1 179.69(16) . . . . ? N2 C122 C123 C115 -178.83(16) . . . . ? C118 C122 C123 C115 0.5(3) . . . . ? C222 N3 C211 C212 1.6(3) . . . . ? Cu1 N3 C211 C212 -170.12(15) . . . . ? N3 C211 C212 C213 -0.9(3) . . . . ? C211 C212 C213 C214 -0.5(3) . . . . ? C212 C213 C214 C222 1.1(3) . . . . ? C212 C213 C214 C215 -178.68(19) . . . . ? C213 C214 C215 C216 -179.75(19) . . . . ? C222 C214 C215 C216 0.5(3) . . . . ? C214 C215 C216 C217 -0.1(3) . . . . ? C215 C216 C217 C218 -179.9(2) . . . . ? C215 C216 C217 C221 0.9(3) . . . . ? C221 C217 C218 C219 0.5(3) . . . . ? C216 C217 C218 C219 -178.71(19) . . . . ? C217 C218 C219 C220 1.6(3) . . . . ? C221 N4 C220 C219 1.0(3) . . . . ? Cu1 N4 C220 C219 177.02(15) . . . . ? C218 C219 C220 N4 -2.5(3) . . . . ? C220 N4 C221 C217 1.3(3) . . . . ? Cu1 N4 C221 C217 -175.62(14) . . . . ? C220 N4 C221 C222 -179.49(17) . . . . ? Cu1 N4 C221 C222 3.64(19) . . . . ? C218 C217 C221 N4 -2.0(3) . . . . ? C216 C217 C221 N4 177.24(17) . . . . ? C218 C217 C221 C222 178.73(17) . . . . ? C216 C217 C221 C222 -2.0(3) . . . . ? C211 N3 C222 C214 -1.0(3) . . . . ? Cu1 N3 C222 C214 171.47(14) . . . . ? C211 N3 C222 C221 -179.94(16) . . . . ? Cu1 N3 C222 C221 -7.5(2) . . . . ? C213 C214 C222 N3 -0.3(3) . . . . ? C215 C214 C222 N3 179.43(17) . . . . ? C213 C214 C222 C221 178.58(17) . . . . ? C215 C214 C222 C221 -1.7(3) . . . . ? N4 C221 C222 N3 2.1(2) . . . . ? C217 C221 C222 N3 -178.62(16) . . . . ? N4 C221 C222 C214 -176.88(16) . . . . ? C217 C221 C222 C214 2.4(3) . . . . ? C2T C1S C2S O1S -53.7(14) . . . . ? C2S C1S C2T O1S 72.8(12) . . . . ? C1S C2T O1S C2S -46.8(7) . . . . ? C1S C2S O1S C2T 83.8(13) . . . . ? 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 O1W H11W O12 0.945(17) 1.842(17) 2.786(2) 175(3) . O1W H21W O2W 0.960(13) 1.800(13) 2.741(2) 166(2) . O2W H12W O3W 0.940(17) 1.935(19) 2.845(3) 162(3) . O2W H22W O1W 0.930(15) 1.862(16) 2.755(2) 160.3(19) 2_676 O3W H13W O4W 0.886(17) 1.949(19) 2.804(2) 161(3) . O3W H23W O19 0.876(17) 1.879(18) 2.742(2) 168(3) 1_545 O4W H14W O20 0.898(17) 1.814(17) 2.708(2) 174(3) 1_545 O4W H24W O5W 0.880(17) 1.900(18) 2.767(3) 168(3) 2_666 O5W H15W O20 0.91(3) 1.86(3) 2.763(2) 171(3) 1_545 O5W H25W O2W 0.77(3) 2.10(3) 2.788(3) 150(3) 2_666 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.028 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.075 data_jgb88 _database_code_depnum_ccdc_archive 'CCDC 783512' #TrackingRef '- complex 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H79 Cu2 N8 O23.50' _chemical_formula_weight 1511.47 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' 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 12.598(2) _cell_length_b 12.866(2) _cell_length_c 13.330(3) _cell_angle_alpha 100.665(14) _cell_angle_beta 108.868(15) _cell_angle_gamma 107.973(12) _cell_volume 1844.7(6) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 4.85 _cell_measurement_theta_max 12.47 _exptl_crystal_description lozenge _exptl_crystal_colour blue _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 789 _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.6387 _exptl_absorpt_correction_T_max 0.8910 _exptl_absorpt_process_details 'Siemens XSCANS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6627 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6314 _reflns_number_gt 4973 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0869P)^2^+3.9663P] 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 6314 _refine_ls_number_parameters 505 _refine_ls_number_restraints 49 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1713 _refine_ls_wR_factor_gt 0.1583 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _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 Cu Cu 0.53664(5) 0.79685(4) 0.25174(4) 0.01929(18) Uani 1 1 d . . . N1A N 0.4468(3) 0.8712(3) 0.3174(3) 0.0215(8) Uani 1 1 d . . . C1A C 0.3466(4) 0.8212(4) 0.3328(4) 0.0278(10) Uani 1 1 d . . . H1A H 0.3140 0.7399 0.3166 0.033 Uiso 1 1 calc R . . C2A C 0.2873(5) 0.8843(5) 0.3722(4) 0.0357(12) Uani 1 1 d . . . H2A H 0.2159 0.8461 0.3826 0.043 Uiso 1 1 calc R . . C3A C 0.3326(5) 1.0008(5) 0.3954(4) 0.0361(12) Uani 1 1 d . . . H3A H 0.2931 1.0442 0.4226 0.043 Uiso 1 1 calc R . . C4A C 0.4378(5) 1.0568(4) 0.3792(4) 0.0304(11) Uani 1 1 d . . . C5A C 0.4935(6) 1.1785(5) 0.4008(5) 0.0446(14) Uani 1 1 d . . . H5A H 0.4567 1.2261 0.4259 0.054 Uiso 1 1 calc R . . C6A C 0.5963(6) 1.2275(4) 0.3866(4) 0.0430(14) Uani 1 1 d . . . H6A H 0.6316 1.3087 0.4032 0.052 Uiso 1 1 calc R . . C7A C 0.6530(5) 1.1578(4) 0.3465(4) 0.0337(12) Uani 1 1 d . . . C8A C 0.7599(5) 1.2024(4) 0.3276(4) 0.0403(13) Uani 1 1 d . . . H8A H 0.8009 1.2830 0.3443 0.048 Uiso 1 1 calc R . . C9A C 0.8030(5) 1.1276(5) 0.2851(5) 0.0404(13) Uani 1 1 d . . . H9A H 0.8738 1.1560 0.2706 0.048 Uiso 1 1 calc R . . C10A C 0.7432(4) 1.0094(4) 0.2628(4) 0.0309(11) Uani 1 1 d . . . H10A H 0.7751 0.9589 0.2337 0.037 Uiso 1 1 calc R . . N2A N 0.6442(3) 0.9652(3) 0.2807(3) 0.0229(8) Uani 1 1 d . . . C11A C 0.5994(4) 1.0384(4) 0.3222(3) 0.0245(10) Uani 1 1 d . . . C12A C 0.4918(4) 0.9881(4) 0.3402(3) 0.0235(10) Uani 1 1 d . . . N1B N 0.3994(3) 0.7316(3) 0.0795(3) 0.0242(8) Uani 1 1 d . . . C1B C 0.2883(4) 0.7301(5) 0.0361(4) 0.0355(12) Uani 1 1 d . . . H1B H 0.2591 0.7660 0.0839 0.043 Uiso 1 1 calc R . . C2B C 0.2121(5) 0.6773(5) -0.0781(5) 0.0444(14) Uani 1 1 d . . . H2B H 0.1326 0.6774 -0.1068 0.053 Uiso 1 1 calc R . . C3B C 0.2528(5) 0.6263(5) -0.1468(4) 0.0417(13) Uani 1 1 d . . . H3B H 0.2017 0.5904 -0.2242 0.050 Uiso 1 1 calc R . . C4B C 0.3711(5) 0.6260(4) -0.1045(4) 0.0325(11) Uani 1 1 d . . . C5B C 0.4215(5) 0.5727(5) -0.1700(4) 0.0409(13) Uani 1 1 d . . . H5B H 0.3750 0.5364 -0.2481 0.049 Uiso 1 1 calc R . . C6B C 0.5331(6) 0.5730(4) -0.1233(4) 0.0425(14) Uani 1 1 d . . . H6B H 0.5642 0.5370 -0.1691 0.051 Uiso 1 1 calc R . . C7B C 0.6064(5) 0.6262(4) -0.0061(4) 0.0308(11) Uani 1 1 d . . . C8B C 0.7228(5) 0.6271(4) 0.0468(4) 0.0360(12) Uani 1 1 d . . . H8B H 0.7575 0.5918 0.0044 0.043 Uiso 1 1 calc R . . C9B C 0.7864(5) 0.6788(4) 0.1599(5) 0.0348(12) Uani 1 1 d . . . H9B H 0.8655 0.6802 0.1965 0.042 Uiso 1 1 calc R . . C10B C 0.7332(4) 0.7298(4) 0.2209(4) 0.0265(10) Uani 1 1 d . . . H10B H 0.7777 0.7657 0.2993 0.032 Uiso 1 1 calc R . . N2B N 0.6229(3) 0.7297(3) 0.1730(3) 0.0217(8) Uani 1 1 d . . . C11B C 0.5591(4) 0.6796(4) 0.0608(4) 0.0234(10) Uani 1 1 d . . . C12B C 0.4399(4) 0.6793(4) 0.0107(4) 0.0236(10) Uani 1 1 d . . . O1 O 0.4777(3) 0.6593(2) 0.2985(2) 0.0230(7) Uani 1 1 d . . . O2 O 0.6633(3) 0.7519(3) 0.4344(3) 0.0291(7) Uani 1 1 d . . . C1 C 0.5604(4) 0.6697(4) 0.3894(3) 0.0198(9) Uani 1 1 d . . . C2 C 0.5296(4) 0.5810(4) 0.4455(3) 0.0196(9) Uani 1 1 d . . . C3 C 0.4107(4) 0.4986(4) 0.4056(4) 0.0254(10) Uani 1 1 d . . . H3 H 0.3490 0.4972 0.3407 0.031 Uiso 1 1 calc R . . C4 C 0.6181(4) 0.5805(4) 0.5410(4) 0.0254(10) Uani 1 1 d . . . H4 H 0.6995 0.6359 0.5694 0.031 Uiso 1 1 calc R . . O3 O 0.9565(3) 0.3577(3) -0.2945(3) 0.0365(8) Uani 1 1 d . . . O4 O 0.8806(4) 0.4924(3) -0.2842(3) 0.0425(9) Uani 1 1 d . . . C5 C 0.9312(4) 0.4371(4) -0.3239(4) 0.0274(10) Uani 1 1 d . . . C6 C 0.9670(4) 0.4695(4) -0.4156(4) 0.0235(10) Uani 1 1 d . . . C7 C 1.0575(4) 0.4426(4) -0.4390(4) 0.0248(10) Uani 1 1 d . . . H7 H 1.0974 0.4032 -0.3971 0.030 Uiso 1 1 calc R . . C8 C 0.9106(4) 0.5271(4) -0.4774(4) 0.0248(10) Uani 1 1 d . . . H8 H 0.8491 0.5462 -0.4622 0.030 Uiso 1 1 calc R . . O1W O 0.9027(3) 0.8064(3) -0.4357(3) 0.0394(9) Uani 1 1 d D . . H1WA H 0.905(5) 0.776(5) -0.387(4) 0.059 Uiso 1 1 d D . . H1WB H 0.833(3) 0.796(5) -0.475(4) 0.059 Uiso 1 1 d D . . O3W O 0.9473(4) 1.3107(4) 0.8984(4) 0.0567(12) Uani 1 1 d D . . H3WA H 0.953(7) 1.335(5) 0.847(4) 0.085 Uiso 1 1 d D . . H3WB H 0.946(8) 1.244(3) 0.885(6) 0.085 Uiso 1 1 d D . . O4W O 1.0337(4) 0.8312(3) 0.4303(4) 0.0508(10) Uani 1 1 d D . . H4WA H 0.990(6) 0.820(5) 0.466(5) 0.076 Uiso 1 1 d D . . H4WB H 1.020(6) 0.768(3) 0.388(5) 0.076 Uiso 1 1 d D . . O5W O 1.0064(4) 1.0345(4) 0.7018(4) 0.0562(11) Uani 1 1 d D . . H5WA H 1.004(7) 1.073(4) 0.657(4) 0.084 Uiso 1 1 d D . . H5WB H 0.969(6) 0.965(2) 0.663(5) 0.084 Uiso 1 1 d D . . O6W O 0.8653(5) 0.5121(5) -0.0816(4) 0.0832(17) Uani 1 1 d . . . H6WA H 0.8701 0.5054 -0.1444 0.125 Uiso 1 1 d . . . H6WB H 0.9229 0.5659 -0.0253 0.125 Uiso 1 1 d . . . O7W O 0.9599(7) 1.1002(5) 0.8841(5) 0.095(2) Uani 1 1 d D . . H7WB H 0.965(10) 1.050(7) 0.915(7) 0.143 Uiso 1 1 d D . . H7WA H 0.973(11) 1.082(8) 0.826(6) 0.143 Uiso 1 1 d D . . O20 O 0.9375(4) 0.7242(4) -0.2558(4) 0.0620(12) Uani 0.50 1 d PDU A -1 H20 H 0.9195 0.6520 -0.2645 0.093 Uiso 0.50 1 d P B -1 C20 C 0.9328(14) 0.7862(13) -0.1620(12) 0.068(4) Uani 0.50 1 d PDU A -1 H20A H 0.9750 0.8679 -0.1547 0.082 Uiso 0.50 1 calc PR A -1 H20B H 0.9876 0.7718 -0.0989 0.082 Uiso 0.50 1 calc PR A -1 C21 C 0.8300(13) 0.7831(12) -0.1353(15) 0.074(4) Uani 0.50 1 d PDU A -1 H21A H 0.8586 0.8413 -0.0630 0.111 Uiso 0.50 1 calc PR A -1 H21B H 0.7893 0.7066 -0.1311 0.111 Uiso 0.50 1 calc PR A -1 H21C H 0.7723 0.7992 -0.1934 0.111 Uiso 0.50 1 calc PR A -1 O30 O 0.579(2) 0.953(2) -0.039(2) 0.101(8) Uiso 0.25 1 d PDU C -1 C30 C 0.700(2) 0.976(2) -0.025(2) 0.057(6) Uiso 0.25 1 d PDU C -1 H30A H 0.7204 0.9100 -0.0124 0.068 Uiso 0.25 1 calc PR C -1 H30B H 0.7565 1.0447 0.0415 0.068 Uiso 0.25 1 calc PR C -1 C31 C 0.718(2) 0.997(2) -0.1215(18) 0.115(7) Uiso 0.25 1 d PDU C -1 H31A H 0.8045 1.0201 -0.1074 0.172 Uiso 0.25 1 calc PR C -1 H31B H 0.6921 1.0590 -0.1375 0.172 Uiso 0.25 1 calc PR C -1 H31C H 0.6691 0.9268 -0.1857 0.172 Uiso 0.25 1 calc PR C -1 O30' O 0.762(3) 0.853(3) -0.133(3) 0.141(11) Uiso 0.25 1 d PDU D -2 C30' C 0.713(4) 0.911(3) -0.068(3) 0.089(10) Uiso 0.25 1 d PDU D -2 H30C H 0.6286 0.8626 -0.0807 0.107 Uiso 0.25 1 calc PR D -2 H30D H 0.7662 0.9424 0.0129 0.107 Uiso 0.25 1 calc PR D -2 C31' C 0.718(2) 0.997(2) -0.1215(18) 0.115(7) Uiso 0.25 1 d PU D -2 H31D H 0.6842 1.0488 -0.0921 0.172 Uiso 0.25 1 calc PR D -2 H31E H 0.6700 0.9606 -0.2022 0.172 Uiso 0.25 1 calc PR D -2 H31F H 0.8030 1.0416 -0.1070 0.172 Uiso 0.25 1 calc PR D -2 O2W' O 0.8807(16) 0.8775(15) -0.0926(14) 0.054(4) Uiso 0.25 1 d P E -3 O2W O 0.9375(4) 0.7242(4) -0.2558(4) 0.0620(12) Uani 0.50 1 d P F -3 H2WA H 0.9195 0.6520 -0.2645 0.093 Uiso 0.50 1 d P G -3 H2WB H 0.9072 0.7673 -0.2296 0.093 Uiso 0.50 1 d P H -3 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 Cu 0.0199(3) 0.0189(3) 0.0206(3) 0.0056(2) 0.0095(2) 0.0088(2) N1A 0.0204(19) 0.0240(19) 0.0172(18) 0.0039(15) 0.0049(15) 0.0097(16) C1A 0.025(2) 0.029(3) 0.028(2) 0.006(2) 0.012(2) 0.009(2) C2A 0.026(3) 0.051(3) 0.034(3) 0.011(2) 0.015(2) 0.017(2) C3A 0.042(3) 0.049(3) 0.029(3) 0.007(2) 0.018(2) 0.032(3) C4A 0.041(3) 0.032(3) 0.022(2) 0.006(2) 0.011(2) 0.023(2) C5A 0.070(4) 0.035(3) 0.037(3) 0.008(2) 0.024(3) 0.031(3) C6A 0.069(4) 0.022(3) 0.035(3) 0.006(2) 0.021(3) 0.017(3) C7A 0.043(3) 0.024(2) 0.022(2) 0.0063(19) 0.006(2) 0.008(2) C8A 0.045(3) 0.026(3) 0.035(3) 0.013(2) 0.007(3) 0.002(2) C9A 0.026(3) 0.043(3) 0.045(3) 0.023(3) 0.011(2) 0.002(2) C10A 0.025(3) 0.031(3) 0.035(3) 0.014(2) 0.011(2) 0.008(2) N2A 0.0204(19) 0.0232(19) 0.0238(19) 0.0102(16) 0.0058(16) 0.0089(16) C11A 0.028(2) 0.025(2) 0.016(2) 0.0072(18) 0.0049(19) 0.009(2) C12A 0.026(2) 0.025(2) 0.017(2) 0.0042(18) 0.0043(18) 0.013(2) N1B 0.023(2) 0.028(2) 0.0204(19) 0.0098(16) 0.0074(16) 0.0087(17) C1B 0.027(3) 0.049(3) 0.031(3) 0.015(2) 0.008(2) 0.020(2) C2B 0.026(3) 0.059(4) 0.038(3) 0.016(3) 0.001(2) 0.015(3) C3B 0.039(3) 0.045(3) 0.022(3) 0.010(2) 0.000(2) 0.007(3) C4B 0.039(3) 0.026(2) 0.024(2) 0.009(2) 0.010(2) 0.005(2) C5B 0.053(4) 0.038(3) 0.021(2) 0.001(2) 0.014(2) 0.010(3) C6B 0.065(4) 0.029(3) 0.032(3) 0.001(2) 0.030(3) 0.010(3) C7B 0.041(3) 0.023(2) 0.034(3) 0.008(2) 0.024(2) 0.011(2) C8B 0.043(3) 0.033(3) 0.046(3) 0.011(2) 0.032(3) 0.019(2) C9B 0.033(3) 0.033(3) 0.050(3) 0.015(2) 0.024(3) 0.018(2) C10B 0.024(2) 0.026(2) 0.036(3) 0.011(2) 0.015(2) 0.013(2) N2B 0.0231(19) 0.0210(19) 0.0218(19) 0.0063(15) 0.0108(16) 0.0081(16) C11B 0.027(2) 0.017(2) 0.025(2) 0.0064(18) 0.013(2) 0.0051(18) C12B 0.026(2) 0.020(2) 0.021(2) 0.0075(18) 0.0087(19) 0.0046(19) O1 0.0256(17) 0.0236(16) 0.0219(16) 0.0089(13) 0.0100(14) 0.0111(13) O2 0.0282(18) 0.0246(17) 0.0291(17) 0.0097(14) 0.0096(15) 0.0052(15) C1 0.023(2) 0.019(2) 0.021(2) 0.0060(17) 0.0115(19) 0.0111(19) C2 0.022(2) 0.019(2) 0.019(2) 0.0033(17) 0.0099(18) 0.0099(18) C3 0.022(2) 0.028(2) 0.026(2) 0.0106(19) 0.0070(19) 0.012(2) C4 0.017(2) 0.024(2) 0.033(3) 0.0097(19) 0.0079(19) 0.0062(18) O3 0.048(2) 0.040(2) 0.037(2) 0.0218(16) 0.0251(18) 0.0243(18) O4 0.056(2) 0.060(2) 0.042(2) 0.0276(19) 0.0333(19) 0.040(2) C5 0.025(2) 0.032(3) 0.025(2) 0.010(2) 0.009(2) 0.011(2) C6 0.021(2) 0.023(2) 0.018(2) 0.0002(18) 0.0036(18) 0.0079(19) C7 0.024(2) 0.024(2) 0.020(2) 0.0047(18) 0.0030(19) 0.0097(19) C8 0.021(2) 0.028(2) 0.026(2) 0.0065(19) 0.0092(19) 0.0113(19) O1W 0.0270(19) 0.042(2) 0.047(2) 0.0162(18) 0.0105(17) 0.0148(17) O3W 0.057(3) 0.089(4) 0.049(3) 0.037(3) 0.033(2) 0.039(3) O4W 0.061(3) 0.046(2) 0.060(3) 0.019(2) 0.037(2) 0.025(2) O5W 0.056(3) 0.038(2) 0.068(3) 0.014(2) 0.017(2) 0.021(2) O6W 0.114(5) 0.090(4) 0.062(3) 0.014(3) 0.063(3) 0.038(3) O7W 0.144(6) 0.075(4) 0.071(4) 0.041(3) 0.047(4) 0.033(4) O20 0.065(3) 0.055(3) 0.059(3) 0.018(2) 0.020(2) 0.020(2) C20 0.080(9) 0.068(9) 0.060(8) 0.018(7) 0.030(8) 0.033(8) C21 0.056(8) 0.040(7) 0.127(13) 0.016(8) 0.048(9) 0.014(6) O2W 0.065(3) 0.055(3) 0.059(3) 0.018(2) 0.020(2) 0.020(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 Cu N1A 1.990(4) . y Cu O1 1.993(3) . y Cu N2B 2.002(4) . y Cu N2A 2.053(4) . y Cu N1B 2.188(4) . y N1A C1A 1.329(6) . ? N1A C12A 1.367(6) . ? C1A C2A 1.402(7) . ? C2A C3A 1.361(8) . ? C3A C4A 1.406(7) . ? C4A C12A 1.395(6) . ? C4A C5A 1.432(7) . ? C5A C6A 1.345(8) . ? C6A C7A 1.437(8) . ? C7A C11A 1.398(6) . ? C7A C8A 1.414(8) . ? C8A C9A 1.364(8) . ? C9A C10A 1.396(7) . ? C10A N2A 1.320(6) . ? N2A C11A 1.360(6) . ? C11A C12A 1.429(7) . ? N1B C1B 1.322(6) . ? N1B C12B 1.357(6) . ? C1B C2B 1.404(7) . ? C2B C3B 1.350(8) . ? C3B C4B 1.414(8) . ? C4B C12B 1.401(6) . ? C4B C5B 1.429(7) . ? C5B C6B 1.340(8) . ? C6B C7B 1.430(7) . ? C7B C8B 1.402(7) . ? C7B C11B 1.411(6) . ? C8B C9B 1.370(7) . ? C9B C10B 1.402(7) . ? C10B N2B 1.328(6) . ? N2B C11B 1.359(6) . ? C11B C12B 1.430(6) . ? O1 C1 1.268(5) . ? O2 C1 1.254(5) . ? C1 C2 1.498(6) . ? C2 C3 1.396(6) . ? C2 C4 1.397(6) . ? C3 C4 1.372(6) 2_666 ? C4 C3 1.372(6) 2_666 ? O3 C5 1.251(6) . ? O4 C5 1.247(6) . ? C5 C6 1.517(6) . ? C6 C8 1.379(6) . ? C6 C7 1.396(6) . ? C7 C8 1.382(6) 2_764 ? C8 C7 1.381(6) 2_764 ? O20 C20 1.382(13) . ? C20 C21 1.441(17) . ? O30 C30 1.41(2) . ? C30 C31 1.43(2) . ? O30' C30' 1.45(2) . ? 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 N1A Cu O1 91.31(14) . . y N1A Cu N2B 173.98(15) . . y O1 Cu N2B 93.61(13) . . y N1A Cu N2A 81.96(15) . . y O1 Cu N2A 153.67(13) . . y N2B Cu N2A 95.07(15) . . y N1A Cu N1B 95.91(14) . . y O1 Cu N1B 98.65(13) . . y N2B Cu N1B 79.92(15) . . y N2A Cu N1B 107.33(14) . . y C1A N1A C12A 118.2(4) . . ? C1A N1A Cu 128.4(3) . . ? C12A N1A Cu 113.3(3) . . ? N1A C1A C2A 122.2(4) . . ? C3A C2A C1A 119.6(5) . . ? C2A C3A C4A 120.0(4) . . ? C12A C4A C3A 117.1(4) . . ? C12A C4A C5A 118.1(5) . . ? C3A C4A C5A 124.8(5) . . ? C6A C5A C4A 122.1(5) . . ? C5A C6A C7A 120.4(5) . . ? C11A C7A C8A 117.1(5) . . ? C11A C7A C6A 118.9(5) . . ? C8A C7A C6A 123.9(5) . . ? C9A C8A C7A 118.9(5) . . ? C8A C9A C10A 120.1(5) . . ? N2A C10A C9A 122.5(5) . . ? C10A N2A C11A 118.1(4) . . ? C10A N2A Cu 130.6(3) . . ? C11A N2A Cu 111.3(3) . . ? N2A C11A C7A 123.2(4) . . ? N2A C11A C12A 116.9(4) . . ? C7A C11A C12A 119.9(4) . . ? N1A C12A C4A 123.1(4) . . ? N1A C12A C11A 116.4(4) . . ? C4A C12A C11A 120.5(4) . . ? C1B N1B C12B 118.4(4) . . ? C1B N1B Cu 131.9(3) . . ? C12B N1B Cu 109.6(3) . . ? N1B C1B C2B 122.3(5) . . ? C3B C2B C1B 119.3(5) . . ? C2B C3B C4B 120.5(5) . . ? C12B C4B C3B 116.2(5) . . ? C12B C4B C5B 119.2(5) . . ? C3B C4B C5B 124.6(5) . . ? C6B C5B C4B 121.3(5) . . ? C5B C6B C7B 121.4(5) . . ? C8B C7B C11B 117.9(4) . . ? C8B C7B C6B 123.5(5) . . ? C11B C7B C6B 118.6(5) . . ? C9B C8B C7B 119.7(4) . . ? C8B C9B C10B 119.1(5) . . ? N2B C10B C9B 122.4(5) . . ? C10B N2B C11B 119.2(4) . . ? C10B N2B Cu 125.9(3) . . ? C11B N2B Cu 114.9(3) . . ? N2B C11B C7B 121.7(4) . . ? N2B C11B C12B 118.5(4) . . ? C7B C11B C12B 119.9(4) . . ? N1B C12B C4B 123.3(4) . . ? N1B C12B C11B 117.1(4) . . ? C4B C12B C11B 119.7(4) . . ? C1 O1 Cu 108.6(3) . . ? O2 C1 O1 122.9(4) . . ? O2 C1 C2 119.8(4) . . ? O1 C1 C2 117.2(4) . . ? C3 C2 C4 118.2(4) . . ? C3 C2 C1 120.8(4) . . ? C4 C2 C1 121.1(4) . . ? C4 C3 C2 120.6(4) 2_666 . ? C3 C4 C2 121.2(4) 2_666 . ? O4 C5 O3 126.1(4) . . ? O4 C5 C6 117.1(4) . . ? O3 C5 C6 116.8(4) . . ? C8 C6 C7 118.7(4) . . ? C8 C6 C5 120.3(4) . . ? C7 C6 C5 121.1(4) . . ? C8 C7 C6 120.5(4) 2_764 . ? C6 C8 C7 120.8(4) . 2_764 ? O20 C20 C21 130.6(13) . . ? O30 C30 C31 110.9(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 O1W H1WA O2W 0.823(19) 1.94(2) 2.758(6) 170(6) . O1W H1WA O20 0.823(19) 1.94(2) 2.758(6) 170(6) . O1W H1WB O2 0.816(19) 1.92(2) 2.730(5) 172(6) 1_554 O3W H3WA O3 0.82(2) 1.97(3) 2.778(5) 167(6) 1_566 O3W H3WB O7W 0.83(2) 1.92(2) 2.737(8) 169(7) . O4W H4WA O1W 0.84(2) 1.96(2) 2.795(6) 173(7) 1_556 O4W H4WB O3 0.83(2) 2.01(3) 2.811(5) 161(6) 2_765 O5W H5WA O4W 0.84(2) 1.91(3) 2.727(6) 164(8) 2_776 O5W H5WB O1W 0.84(2) 1.96(3) 2.788(6) 170(8) 1_556 O6W H6WA O4 0.85 1.89 2.740(6) 179.2 . O6W H6WB O3W 0.85 1.92 2.761(7) 179.2 2_776 O7W H7WB O2W' 0.83(2) 2.31(10) 2.753(19) 114(9) 2_776 O7W H7WB O2W' 0.83(2) 2.11(7) 2.840(19) 146(10) 1_556 O7W H7WA O5W 0.84(2) 1.88(2) 2.725(8) 176(10) . O20 H20 O4 0.86 1.90 2.763(6) 179.6 . O2W H2WA O4 0.86 1.90 2.763(6) 179.6 . O2W H2WB O2W' 0.85 2.28 3.070(18) 155.5 . _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.204 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.100