# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'E. Gumienna-Kontecka' _publ_contact_author_address ; 14, F. Joliot-Curie Wroclaw ; _publ_contact_author_email kontecka@wchuwr.pl #TrackingRef '- 1a.cif' _publ_contact_author 'Igor O.Fritsky' _publ_author_name E.Gumienna-Kontecka # Attachment '- 1a.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 764186' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H34 Cu2 N8 O10, 2(C H4 O), 2(Cl O4)' _chemical_formula_sum 'C20 H42 Cl2 Cu2 N8 O20' _chemical_formula_weight 912.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4897(6) _cell_length_b 22.8077(11) _cell_length_c 7.7354(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.518(3) _cell_angle_gamma 90.00 _cell_volume 1825.19(16) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1623 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7767 _exptl_absorpt_correction_T_max 0.8962 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _publ_section_exptl_refinement ; The NH and OH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.97 \%A from atom O9 and the deepest hole is located 0.84 \%A from atom Pt1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18544 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3077 _reflns_number_gt 2418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker, 2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0290P)^2^+5.4147P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3077 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 Cu1 Cu 0.52363(5) 0.09216(2) 0.72037(7) 0.02601(17) Uani 1 1 d . . . Cl1 Cl 0.03561(10) 0.10113(5) 0.71674(14) 0.0322(3) Uani 1 1 d . . . O1 O 0.6485(3) 0.07427(13) 0.9307(4) 0.0291(7) Uani 1 1 d . . . O2 O 0.6142(3) 0.20154(12) 0.5934(4) 0.0303(7) Uani 1 1 d . . . H2O H 0.5517 0.1843 0.5163 0.045 Uiso 1 1 d R . . O3 O 0.5696(3) -0.01734(12) 1.3060(4) 0.0273(7) Uani 1 1 d . . . O4 O 0.5598(3) -0.15245(13) 1.6099(4) 0.0324(7) Uani 1 1 d . . . O5 O 0.3853(3) 0.13683(15) 0.8645(5) 0.0449(9) Uani 1 1 d . . . H5O H 0.3022 0.1264 0.8551 0.067 Uiso 1 1 d R . . O7 O -0.0311(3) 0.14853(15) 0.6172(4) 0.0427(8) Uani 1 1 d . . . O8 O -0.0565(3) 0.05959(16) 0.7600(4) 0.0478(9) Uani 1 1 d . . . O9 O 0.1184(4) 0.0735(2) 0.6119(6) 0.0753(14) Uani 1 1 d . . . O10 O 0.1088(4) 0.12372(19) 0.8741(5) 0.0663(12) Uani 1 1 d . . . O11 O 0.0206(3) 0.17827(15) 0.2810(4) 0.0390(8) Uani 1 1 d . . . H11O H 0.0323 0.1704 0.4030 0.059 Uiso 1 1 d R . . N1 N 0.6362(3) 0.15996(15) 0.7163(5) 0.0254(8) Uani 1 1 d . . . N2 N 0.5730(3) -0.10399(15) 1.5154(5) 0.0275(8) Uani 1 1 d . . . N3 N 0.7223(3) 0.03207(15) 1.4895(4) 0.0258(8) Uani 1 1 d . . . H3N H 0.7934 0.0325 1.5829 0.039 Uiso 1 1 d R . . N4 N 0.8189(3) 0.11204(15) 1.1086(4) 0.0269(8) Uani 1 1 d . . . H4N H 0.8856 0.1366 1.1413 0.040 Uiso 1 1 d R . . C1 C 0.7316(4) 0.11438(18) 0.9677(6) 0.0261(9) Uani 1 1 d . . . C2 C 0.7283(4) 0.16581(18) 0.8477(6) 0.0262(9) Uani 1 1 d . . . C3 C 0.8148(4) 0.21820(19) 0.8794(6) 0.0300(10) Uani 1 1 d . . . H3A H 0.8292 0.2344 0.7669 0.045 Uiso 1 1 calc R . . H3B H 0.8978 0.2066 0.9486 0.045 Uiso 1 1 calc R . . H3C H 0.7740 0.2480 0.9436 0.045 Uiso 1 1 calc R . . C4 C 0.6463(4) -0.01441(18) 1.4499(6) 0.0256(9) Uani 1 1 d . . . C5 C 0.6508(4) -0.06282(18) 1.5804(5) 0.0250(9) Uani 1 1 d . . . C6 C 0.7311(4) -0.0629(2) 1.7569(6) 0.0333(10) Uani 1 1 d . . . H6A H 0.8225 -0.0662 1.7455 0.050 Uiso 1 1 calc R . . H6B H 0.7067 -0.0962 1.8245 0.050 Uiso 1 1 calc R . . H6C H 0.7173 -0.0262 1.8174 0.050 Uiso 1 1 calc R . . C7 C 0.7268(4) 0.07885(18) 1.3610(5) 0.0262(9) Uani 1 1 d . . . H7A H 0.7543 0.1158 1.4230 0.031 Uiso 1 1 calc R . . H7B H 0.6392 0.0849 1.2930 0.031 Uiso 1 1 calc R . . C8 C 0.8201(4) 0.06401(18) 1.2361(5) 0.0261(9) Uani 1 1 d . . . H8A H 0.9084 0.0589 1.3027 0.031 Uiso 1 1 calc R . . H8B H 0.7936 0.0269 1.1739 0.031 Uiso 1 1 calc R . . C9 C 0.1279(5) 0.2142(2) 0.2608(8) 0.0470(13) Uani 1 1 d . . . H9A H 0.1142 0.2539 0.3026 0.071 Uiso 1 1 calc R . . H9B H 0.1368 0.2158 0.1367 0.071 Uiso 1 1 calc R . . H9C H 0.2069 0.1977 0.3290 0.071 Uiso 1 1 calc R . . C13 C 0.4092(5) 0.1909(2) 0.9521(7) 0.0443(13) Uani 1 1 d . . . H13A H 0.4935 0.1896 1.0287 0.066 Uiso 1 1 calc R . . H13B H 0.3415 0.1984 1.0228 0.066 Uiso 1 1 calc R . . H13C H 0.4091 0.2224 0.8659 0.066 Uiso 1 1 calc R . . 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 0.0231(3) 0.0294(3) 0.0256(3) 0.0015(2) 0.0045(2) -0.0028(2) Cl1 0.0216(5) 0.0424(6) 0.0330(6) -0.0004(5) 0.0057(5) 0.0002(5) O1 0.0258(16) 0.0329(16) 0.0284(16) 0.0030(13) 0.0035(13) -0.0048(13) O2 0.0290(17) 0.0307(16) 0.0302(17) 0.0043(13) 0.0020(13) -0.0043(13) O3 0.0235(15) 0.0315(16) 0.0263(17) 0.0018(12) 0.0026(13) -0.0041(12) O4 0.0300(17) 0.0312(17) 0.0357(18) 0.0097(14) 0.0042(14) -0.0009(13) O5 0.0280(18) 0.053(2) 0.057(2) -0.0235(17) 0.0179(17) -0.0079(15) O7 0.045(2) 0.046(2) 0.0371(19) 0.0012(15) 0.0065(16) 0.0119(16) O8 0.038(2) 0.062(2) 0.043(2) 0.0036(17) 0.0056(16) -0.0220(17) O9 0.075(3) 0.083(3) 0.083(3) 0.027(2) 0.055(3) 0.041(2) O10 0.067(3) 0.075(3) 0.047(2) 0.005(2) -0.020(2) -0.031(2) O11 0.0330(18) 0.048(2) 0.0351(19) -0.0006(15) 0.0015(15) -0.0105(15) N1 0.0195(19) 0.0296(19) 0.028(2) 0.0026(15) 0.0072(16) 0.0012(15) N2 0.0250(19) 0.029(2) 0.029(2) 0.0017(15) 0.0085(16) 0.0019(15) N3 0.0209(18) 0.0300(19) 0.026(2) 0.0023(15) 0.0039(15) 0.0022(15) N4 0.0206(19) 0.033(2) 0.027(2) 0.0010(15) 0.0046(16) -0.0043(15) C1 0.019(2) 0.032(2) 0.029(2) -0.0022(18) 0.0088(19) -0.0004(18) C2 0.021(2) 0.032(2) 0.027(2) -0.0015(18) 0.0087(19) -0.0006(17) C3 0.028(2) 0.030(2) 0.032(2) -0.0005(19) 0.007(2) -0.0052(19) C4 0.020(2) 0.029(2) 0.030(2) -0.0021(18) 0.0091(19) 0.0005(17) C5 0.019(2) 0.033(2) 0.024(2) 0.0014(18) 0.0057(18) 0.0034(18) C6 0.034(3) 0.039(3) 0.026(2) -0.0008(19) 0.002(2) -0.004(2) C7 0.024(2) 0.028(2) 0.028(2) 0.0001(18) 0.0057(18) -0.0019(17) C8 0.025(2) 0.030(2) 0.022(2) 0.0001(17) 0.0017(19) -0.0006(18) C9 0.032(3) 0.042(3) 0.068(4) -0.003(3) 0.011(3) -0.003(2) C13 0.038(3) 0.042(3) 0.055(3) -0.009(2) 0.016(3) -0.002(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 1.949(3) . ? Cu1 N2 1.953(4) 3_657 ? Cu1 O1 1.955(3) . ? Cu1 O3 1.961(3) 3_657 ? Cu1 O5 2.218(3) . ? Cl1 O10 1.424(4) . ? Cl1 O9 1.430(4) . ? Cl1 O8 1.432(3) . ? Cl1 O7 1.440(3) . ? O1 C1 1.264(5) . ? O2 N1 1.336(4) . ? O2 H2O 0.8996 . ? O3 C4 1.263(5) . ? O3 Cu1 1.961(3) 3_657 ? O4 N2 1.345(4) . ? O5 C13 1.410(6) . ? O5 H5O 0.8956 . ? O11 C9 1.422(6) . ? O11 H11O 0.9484 . ? N1 C2 1.288(5) . ? N2 C5 1.290(5) . ? N2 Cu1 1.953(4) 3_657 ? N3 C4 1.331(5) . ? N3 C7 1.465(5) . ? N3 H3N 0.9487 . ? N4 C1 1.303(5) . ? N4 C8 1.472(5) . ? N4 H4N 0.8990 . ? C1 C2 1.493(6) . ? C2 C3 1.496(6) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.491(6) . ? C5 C6 1.481(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.522(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 N2 95.60(14) . 3_657 ? N1 Cu1 O1 81.65(13) . . ? N2 Cu1 O1 168.07(13) 3_657 . ? N1 Cu1 O3 169.10(13) . 3_657 ? N2 Cu1 O3 81.38(13) 3_657 3_657 ? O1 Cu1 O3 99.15(12) . 3_657 ? N1 Cu1 O5 95.27(13) . . ? N2 Cu1 O5 97.13(14) 3_657 . ? O1 Cu1 O5 94.68(13) . . ? O3 Cu1 O5 95.50(12) 3_657 . ? O10 Cl1 O9 110.7(3) . . ? O10 Cl1 O8 109.2(2) . . ? O9 Cl1 O8 109.7(3) . . ? O10 Cl1 O7 109.3(2) . . ? O9 Cl1 O7 108.4(2) . . ? O8 Cl1 O7 109.5(2) . . ? C1 O1 Cu1 112.3(3) . . ? N1 O2 H2O 100.6 . . ? C4 O3 Cu1 111.8(3) . 3_657 ? C13 O5 Cu1 124.4(3) . . ? C13 O5 H5O 111.4 . . ? Cu1 O5 H5O 123.1 . . ? C9 O11 H11O 104.1 . . ? C2 N1 O2 120.4(3) . . ? C2 N1 Cu1 116.5(3) . . ? O2 N1 Cu1 122.8(3) . . ? C5 N2 O4 120.1(4) . . ? C5 N2 Cu1 117.4(3) . 3_657 ? O4 N2 Cu1 122.5(3) . 3_657 ? C4 N3 C7 120.6(4) . . ? C4 N3 H3N 123.3 . . ? C7 N3 H3N 113.6 . . ? C1 N4 C8 121.2(4) . . ? C1 N4 H4N 128.0 . . ? C8 N4 H4N 110.8 . . ? O1 C1 N4 121.5(4) . . ? O1 C1 C2 118.9(4) . . ? N4 C1 C2 119.6(4) . . ? N1 C2 C1 110.3(4) . . ? N1 C2 C3 124.6(4) . . ? C1 C2 C3 125.1(4) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 N3 121.0(4) . . ? O3 C4 C5 120.1(4) . . ? N3 C4 C5 118.9(4) . . ? N2 C5 C6 125.8(4) . . ? N2 C5 C4 109.2(4) . . ? C6 C5 C4 125.0(4) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 111.4(3) . . ? N3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? N4 C8 C7 108.9(3) . . ? N4 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? N4 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O11 C9 H9A 109.5 . . ? O11 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O11 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 O2 H2O O4 0.90 1.57 2.472(4) 176.9 3_657 O2 H2O N2 0.90 2.24 2.995(5) 141.0 3_657 O5 H5O O10 0.90 2.06 2.929(5) 163.7 . O5 H5O Cl1 0.90 2.88 3.747(3) 162.8 . O11 H11O O7 0.95 1.95 2.826(5) 152.6 . N3 H3N O8 0.95 2.01 2.923(5) 162.3 1_656 N4 H4N O11 0.90 1.89 2.758(5) 161.6 1_656 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.426 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.084 # Attachment '- 1b.cif' data_1b _database_code_depnum_ccdc_archive 'CCDC 764187' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H40 Cu2 N12 O16, C3 H6 O' _chemical_formula_sum 'C25 H46 Cu2 N12 O17' _chemical_formula_weight 913.82 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.511(2) _cell_length_b 9.635(2) _cell_length_c 11.818(2) _cell_angle_alpha 95.34(3) _cell_angle_beta 93.36(3) _cell_angle_gamma 98.13(3) _cell_volume 952.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1738 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_absorpt_coefficient_mu 1.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8186 _exptl_absorpt_correction_T_max 0.8772 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6608 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 28.38 _reflns_number_total 4192 _reflns_number_gt 3568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker, 2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0501P)^2^+0.1428P] 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 4192 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.68492(3) 0.72017(3) 0.87162(2) 0.01374(10) Uani 1 1 d . . . O1 O 0.87370(19) 0.99569(16) 0.85784(14) 0.0169(3) Uani 1 1 d . . . O2 O 0.56950(18) 0.74842(15) 1.01118(13) 0.0149(3) Uani 1 1 d . . . O3 O 0.41497(19) 0.47277(16) 1.19046(13) 0.0146(3) Uani 1 1 d . . . O4 O 0.11027(19) 0.18390(16) 1.30258(14) 0.0182(4) Uani 1 1 d . . . O5 O 0.8695(2) 0.63609(17) 0.97969(14) 0.0207(4) Uani 1 1 d . . . O6 O 0.4552(2) 0.81290(16) 0.74777(14) 0.0197(4) Uani 1 1 d . . . O7 O 0.4225(2) 0.67530(18) 0.58888(15) 0.0256(4) Uani 1 1 d . . . O8 O 0.5002(3) 0.8974(2) 0.58711(18) 0.0474(6) Uani 1 1 d . . . O9 O -0.0932(8) 0.8677(8) 0.3860(6) 0.098(2) Uani 0.50 1 d P . . N1 N 0.7708(2) 0.91864(19) 0.91845(16) 0.0134(4) Uani 1 1 d . . . N2 N 0.5541(2) 0.9091(2) 1.16008(17) 0.0142(4) Uani 1 1 d . . . N3 N 0.4272(2) 0.6277(2) 1.34736(17) 0.0155(4) Uani 1 1 d . . . N4 N 0.2152(2) 0.28917(19) 1.27215(16) 0.0133(4) Uani 1 1 d . . . N5 N 0.8860(2) 0.55743(19) 1.15441(16) 0.0161(4) Uani 1 1 d . . . N6 N 0.4571(2) 0.7962(2) 0.63998(17) 0.0189(4) Uani 1 1 d . . . C1 C 0.7891(3) 1.1194(2) 1.0666(2) 0.0166(5) Uani 1 1 d . . . H1A H 0.8829 1.1565 1.0316 0.025 Uiso 1 1 calc R . . H1B H 0.8143 1.1173 1.1466 0.025 Uiso 1 1 calc R . . H1C H 0.7084 1.1781 1.0559 0.025 Uiso 1 1 calc R . . C2 C 0.7299(3) 0.9738(2) 1.01338(19) 0.0131(4) Uani 1 1 d . . . C3 C 0.6115(3) 0.8703(2) 1.06296(19) 0.0132(4) Uani 1 1 d . . . C4 C 0.4430(3) 0.8122(2) 1.2160(2) 0.0153(5) Uani 1 1 d . . . H4A H 0.3800 0.7446 1.1592 0.018 Uiso 1 1 calc R . . H4B H 0.3712 0.8645 1.2572 0.018 Uiso 1 1 calc R . . C5 C 0.5352(3) 0.7344(2) 1.2989(2) 0.0159(5) Uani 1 1 d . . . H5A H 0.6142 0.6897 1.2591 0.019 Uiso 1 1 calc R . . H5B H 0.5903 0.8014 1.3597 0.019 Uiso 1 1 calc R . . C6 C 0.3729(3) 0.5040(2) 1.28926(19) 0.0137(4) Uani 1 1 d . . . C7 C 0.2566(3) 0.4028(2) 1.34078(19) 0.0142(4) Uani 1 1 d . . . C8 C 0.1957(3) 0.4269(3) 1.4555(2) 0.0224(5) Uani 1 1 d . . . H8A H 0.1028 0.3594 1.4614 0.034 Uiso 1 1 calc R . . H8B H 0.1687 0.5204 1.4661 0.034 Uiso 1 1 calc R . . H8C H 0.2763 0.4163 1.5131 0.034 Uiso 1 1 calc R . . C9 C 0.8163(3) 0.5585(2) 1.0516(2) 0.0180(5) Uani 1 1 d . . . H9 H 0.7219 0.4976 1.0318 0.022 Uiso 1 1 calc R . . C10 C 1.0359(3) 0.6483(3) 1.1879(2) 0.0258(6) Uani 1 1 d . . . H10A H 1.1226 0.5988 1.1687 0.039 Uiso 1 1 calc R . . H10B H 1.0432 0.6746 1.2686 0.039 Uiso 1 1 calc R . . H10C H 1.0411 0.7314 1.1486 0.039 Uiso 1 1 calc R . . C11 C 0.8292(3) 0.4552(3) 1.2309(2) 0.0233(5) Uani 1 1 d . . . H11A H 0.7282 0.4042 1.2004 0.035 Uiso 1 1 calc R . . H11B H 0.8173 0.5032 1.3042 0.035 Uiso 1 1 calc R . . H11C H 0.9043 0.3907 1.2389 0.035 Uiso 1 1 calc R . . C12 C 0.1270(5) 0.9384(5) 0.4971(4) 0.0706(12) Uani 1 1 d . . . C13 C -0.0317(10) 0.9502(8) 0.4580(8) 0.060(2) Uani 0.50 1 d P . . H1O1 H 0.888(4) 0.922(3) 0.788(3) 0.048(10) Uiso 1 1 d . . . H1N3 H 0.404(3) 0.642(3) 1.415(3) 0.029(8) Uiso 1 1 d . . . H1N2 H 0.573(3) 0.990(3) 1.186(3) 0.028(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01749(16) 0.01032(15) 0.01262(15) -0.00003(10) 0.00411(11) -0.00104(10) O1 0.0204(8) 0.0120(8) 0.0176(8) 0.0023(6) 0.0084(7) -0.0030(6) O2 0.0173(8) 0.0118(7) 0.0150(8) -0.0008(6) 0.0044(7) -0.0004(6) O3 0.0183(8) 0.0118(7) 0.0127(8) -0.0009(6) 0.0031(7) 0.0001(6) O4 0.0201(8) 0.0149(8) 0.0181(8) 0.0013(7) 0.0068(7) -0.0042(6) O5 0.0219(9) 0.0221(9) 0.0197(9) 0.0077(7) 0.0042(7) 0.0035(7) O6 0.0279(9) 0.0157(8) 0.0151(8) -0.0017(6) 0.0055(7) 0.0023(7) O7 0.0409(11) 0.0178(9) 0.0163(8) -0.0041(7) 0.0032(8) 0.0008(8) O8 0.0812(18) 0.0289(11) 0.0295(11) 0.0125(9) 0.0045(12) -0.0072(11) O9 0.063(4) 0.113(6) 0.098(5) -0.041(5) 0.022(4) -0.028(4) N1 0.0145(9) 0.0114(9) 0.0141(9) 0.0026(7) 0.0030(8) -0.0002(7) N2 0.0162(9) 0.0094(9) 0.0161(10) 0.0000(8) 0.0030(8) -0.0007(7) N3 0.0197(10) 0.0144(9) 0.0116(9) 0.0013(8) 0.0028(8) -0.0009(8) N4 0.0143(9) 0.0121(9) 0.0132(9) 0.0024(7) 0.0025(8) 0.0000(7) N5 0.0165(9) 0.0153(9) 0.0160(10) 0.0022(8) 0.0008(8) -0.0001(8) N6 0.0212(10) 0.0168(10) 0.0190(10) 0.0019(8) 0.0023(9) 0.0028(8) C1 0.0160(11) 0.0126(11) 0.0195(11) -0.0023(9) 0.0021(10) -0.0013(9) C2 0.0117(10) 0.0121(10) 0.0152(11) 0.0016(8) -0.0005(9) 0.0011(8) C3 0.0125(10) 0.0129(10) 0.0144(10) 0.0015(8) 0.0012(9) 0.0020(8) C4 0.0165(11) 0.0132(10) 0.0163(11) 0.0009(9) 0.0065(9) 0.0007(8) C5 0.0164(11) 0.0142(11) 0.0157(11) 0.0003(9) 0.0023(9) -0.0027(9) C6 0.0146(10) 0.0148(10) 0.0123(10) 0.0013(8) 0.0015(9) 0.0041(8) C7 0.0167(11) 0.0138(10) 0.0121(10) 0.0010(8) 0.0028(9) 0.0015(9) C8 0.0261(13) 0.0205(12) 0.0180(12) -0.0023(10) 0.0071(11) -0.0042(10) C9 0.0165(11) 0.0166(11) 0.0218(12) 0.0027(9) 0.0021(10) 0.0042(9) C10 0.0272(13) 0.0221(13) 0.0254(13) 0.0042(10) -0.0056(11) -0.0045(10) C11 0.0257(13) 0.0221(12) 0.0226(13) 0.0075(10) 0.0052(11) 0.0007(10) C12 0.055(2) 0.078(3) 0.083(3) 0.025(2) 0.022(2) 0.003(2) C13 0.058(5) 0.050(5) 0.070(6) 0.014(4) 0.032(4) -0.016(4) _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 N4 1.9445(19) 2_667 ? Cu1 N1 1.9641(19) . ? Cu1 O2 1.9853(16) . ? Cu1 O3 1.9857(17) 2_667 ? Cu1 O5 2.2525(18) . ? Cu1 O6 2.6767(19) . ? O1 N1 1.349(2) . ? O1 H1O1 1.06(3) . ? O2 C3 1.266(3) . ? O3 C6 1.264(3) . ? O3 Cu1 1.9857(16) 2_667 ? O4 N4 1.343(2) . ? O5 C9 1.247(3) . ? O6 N6 1.270(2) . ? O7 N6 1.249(3) . ? O8 N6 1.230(3) . ? O9 C13 1.155(9) . ? N1 C2 1.284(3) . ? N2 C3 1.317(3) . ? N2 C4 1.464(3) . ? N2 H1N2 0.80(3) . ? N3 C6 1.327(3) . ? N3 C5 1.461(3) . ? N3 H1N3 0.84(3) . ? N4 C7 1.294(3) . ? N4 Cu1 1.9445(19) 2_667 ? N5 C9 1.321(3) . ? N5 C11 1.451(3) . ? N5 C10 1.453(3) . ? C1 C2 1.488(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.499(3) . ? C4 C5 1.533(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.486(3) . ? C7 C8 1.490(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.425(10) . ? C12 C13 1.511(10) 2_576 ? C13 C13 1.346(17) 2_576 ? C13 C12 1.511(10) 2_576 ? 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 N4 Cu1 N1 95.40(8) 2_667 . ? N4 Cu1 O2 172.91(7) 2_667 . ? N1 Cu1 O2 81.05(8) . . ? N4 Cu1 O3 81.73(8) 2_667 2_667 ? N1 Cu1 O3 173.50(7) . 2_667 ? O2 Cu1 O3 101.15(7) . 2_667 ? N4 Cu1 O5 98.77(7) 2_667 . ? N1 Cu1 O5 94.23(7) . . ? O2 Cu1 O5 87.65(7) . . ? O3 Cu1 O5 91.98(7) 2_667 . ? N4 Cu1 O6 83.17(7) 2_667 . ? N1 Cu1 O6 87.31(7) . . ? O2 Cu1 O6 90.50(6) . . ? O3 Cu1 O6 86.56(6) 2_667 . ? O5 Cu1 O6 177.38(5) . . ? N4 Cu1 Cu1 133.27(6) 2_667 2_667 ? N1 Cu1 Cu1 130.82(6) . 2_667 ? O2 Cu1 Cu1 51.35(5) . 2_667 ? O3 Cu1 Cu1 53.02(5) 2_667 2_667 ? O5 Cu1 Cu1 74.57(5) . 2_667 ? O6 Cu1 Cu1 102.82(4) . 2_667 ? N1 O1 H1O1 102.0(19) . . ? C3 O2 Cu1 111.76(14) . . ? C6 O3 Cu1 111.13(14) . 2_667 ? C9 O5 Cu1 115.37(15) . . ? N6 O6 Cu1 117.74(13) . . ? C2 N1 O1 119.66(18) . . ? C2 N1 Cu1 117.33(15) . . ? O1 N1 Cu1 122.96(14) . . ? C3 N2 C4 121.85(19) . . ? C3 N2 H1N2 119(2) . . ? C4 N2 H1N2 118(2) . . ? C6 N3 C5 121.5(2) . . ? C6 N3 H1N3 119(2) . . ? C5 N3 H1N3 120(2) . . ? C7 N4 O4 120.06(19) . . ? C7 N4 Cu1 116.67(16) . 2_667 ? O4 N4 Cu1 123.26(14) . 2_667 ? C9 N5 C11 122.1(2) . . ? C9 N5 C10 119.8(2) . . ? C11 N5 C10 117.6(2) . . ? O8 N6 O7 120.3(2) . . ? O8 N6 O6 120.2(2) . . ? O7 N6 O6 119.41(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 125.5(2) . . ? N1 C2 C3 109.99(19) . . ? C1 C2 C3 124.5(2) . . ? O2 C3 N2 121.7(2) . . ? O2 C3 C2 119.64(19) . . ? N2 C3 C2 118.69(19) . . ? N2 C4 C5 109.92(19) . . ? N2 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N3 C5 C4 110.57(19) . . ? N3 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O3 C6 N3 121.3(2) . . ? O3 C6 C7 119.83(19) . . ? N3 C6 C7 118.9(2) . . ? N4 C7 C6 110.56(19) . . ? N4 C7 C8 124.1(2) . . ? C6 C7 C8 125.36(19) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 N5 124.0(2) . . ? O5 C9 H9 118.0 . . ? N5 C9 H9 118.0 . . ? N5 C10 H10A 109.5 . . ? N5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N5 C11 H11A 109.5 . . ? N5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C13 54.5(6) . 2_576 ? O9 C13 C13 176.5(13) . 2_576 ? O9 C13 C12 117.5(8) . . ? C13 C13 C12 66.0(7) 2_576 . ? O9 C13 C12 117.0(8) . 2_576 ? C13 C13 C12 59.5(7) 2_576 2_576 ? C12 C13 C12 125.5(6) . 2_576 ? 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 N4 Cu1 O2 C3 -64.0(6) 2_667 . . . ? N1 Cu1 O2 C3 -3.62(15) . . . . ? O3 Cu1 O2 C3 -177.41(14) 2_667 . . . ? O5 Cu1 O2 C3 91.04(15) . . . . ? O6 Cu1 O2 C3 -90.82(15) . . . . ? Cu1 Cu1 O2 C3 163.09(17) 2_667 . . . ? N4 Cu1 O5 C9 -142.52(17) 2_667 . . . ? N1 Cu1 O5 C9 121.34(17) . . . . ? O2 Cu1 O5 C9 40.50(17) . . . . ? O3 Cu1 O5 C9 -60.59(17) 2_667 . . . ? O6 Cu1 O5 C9 -4.7(13) . . . . ? Cu1 Cu1 O5 C9 -9.92(15) 2_667 . . . ? N4 Cu1 O6 N6 14.21(15) 2_667 . . . ? N1 Cu1 O6 N6 109.97(15) . . . . ? O2 Cu1 O6 N6 -169.01(15) . . . . ? O3 Cu1 O6 N6 -67.86(15) 2_667 . . . ? O5 Cu1 O6 N6 -123.9(12) . . . . ? Cu1 Cu1 O6 N6 -118.69(14) 2_667 . . . ? N4 Cu1 N1 C2 178.37(17) 2_667 . . . ? O2 Cu1 N1 C2 4.56(16) . . . . ? O3 Cu1 N1 C2 114.9(6) 2_667 . . . ? O5 Cu1 N1 C2 -82.39(17) . . . . ? O6 Cu1 N1 C2 95.49(17) . . . . ? Cu1 Cu1 N1 C2 -9.2(2) 2_667 . . . ? N4 Cu1 N1 O1 -4.17(17) 2_667 . . . ? O2 Cu1 N1 O1 -177.98(17) . . . . ? O3 Cu1 N1 O1 -67.6(7) 2_667 . . . ? O5 Cu1 N1 O1 95.07(16) . . . . ? O6 Cu1 N1 O1 -87.05(16) . . . . ? Cu1 Cu1 N1 O1 168.29(12) 2_667 . . . ? Cu1 O6 N6 O8 -105.3(2) . . . . ? Cu1 O6 N6 O7 71.2(2) . . . . ? O1 N1 C2 C1 -1.2(3) . . . . ? Cu1 N1 C2 C1 176.35(17) . . . . ? O1 N1 C2 C3 178.20(17) . . . . ? Cu1 N1 C2 C3 -4.2(2) . . . . ? Cu1 O2 C3 N2 -177.30(17) . . . . ? Cu1 O2 C3 C2 2.5(2) . . . . ? C4 N2 C3 O2 2.3(3) . . . . ? C4 N2 C3 C2 -177.52(19) . . . . ? N1 C2 C3 O2 1.0(3) . . . . ? C1 C2 C3 O2 -179.6(2) . . . . ? N1 C2 C3 N2 -179.13(19) . . . . ? C1 C2 C3 N2 0.3(3) . . . . ? C3 N2 C4 C5 90.9(3) . . . . ? C6 N3 C5 C4 78.9(3) . . . . ? N2 C4 C5 N3 -174.61(18) . . . . ? Cu1 O3 C6 N3 179.18(17) 2_667 . . . ? Cu1 O3 C6 C7 -2.7(2) 2_667 . . . ? C5 N3 C6 O3 1.4(3) . . . . ? C5 N3 C6 C7 -176.80(19) . . . . ? O4 N4 C7 C6 -179.91(18) . . . . ? Cu1 N4 C7 C6 1.3(2) 2_667 . . . ? O4 N4 C7 C8 0.4(3) . . . . ? Cu1 N4 C7 C8 -178.37(18) 2_667 . . . ? O3 C6 C7 N4 1.0(3) . . . . ? N3 C6 C7 N4 179.2(2) . . . . ? O3 C6 C7 C8 -179.3(2) . . . . ? N3 C6 C7 C8 -1.1(3) . . . . ? Cu1 O5 C9 N5 -143.16(19) . . . . ? C11 N5 C9 O5 -173.4(2) . . . . ? C10 N5 C9 O5 -1.6(4) . . . . ? C13 C12 C13 O9 -179.9(13) 2_576 . . . ? C13 C12 C13 C12 0.000(1) 2_576 . . 2_576 ? 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 O1 H1O1 O4 1.06(3) 1.41(3) 2.468(2) 174(3) 2_667 N3 H1N3 O7 0.84(3) 2.04(3) 2.852(3) 162(3) 1_556 N2 H1N2 O6 0.80(3) 2.04(3) 2.809(3) 162(3) 2_677 _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.893 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.075 # Attachment '- 2a.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 764188' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 Cl Cu N4 O9' _chemical_formula_sum 'C9 H17 Cl Cu N4 O9' _chemical_formula_weight 424.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 11.107(2) _cell_length_b 11.408(2) _cell_length_c 12.134(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.78(3) _cell_angle_gamma 90.00 _cell_volume 1537.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2109 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7306 _exptl_absorpt_correction_T_max 0.7962 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10413 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 28.40 _reflns_number_total 3551 _reflns_number_gt 2843 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker, 2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0429P)^2^+0.0000P] 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 3551 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 Cu1 Cu 0.27880(4) 0.31255(3) 0.52565(3) 0.01782(12) Uani 1 1 d . . . Cl1 Cl 0.01583(6) 0.21982(6) 0.70306(6) 0.01692(17) Uani 1 1 d . . . O1 O 0.1368(2) 0.52194(18) 0.46020(17) 0.0204(5) Uani 1 1 d . . . H1O1 H 0.146(3) 0.474(3) 0.398(3) 0.031 Uiso 1 1 d . . . O2 O 0.31493(19) 0.34160(17) 0.68454(16) 0.0165(5) Uani 1 1 d . . . O3 O 0.17778(18) 0.64401(17) 0.98590(15) 0.0140(4) Uani 1 1 d . . . O4 O 0.33135(19) 0.86852(17) 1.18558(16) 0.0176(5) Uani 1 1 d . . . O5 O 0.4735(2) 0.3770(2) 0.4877(2) 0.0369(6) Uani 1 1 d . . . H105 H 0.5001 0.3722 0.4167 0.056(14) Uiso 1 1 d R . . H205 H 0.5200 0.4056 0.5385 0.085 Uiso 1 1 d R . . O6 O 0.0761(2) 0.2116(2) 0.59861(18) 0.0283(6) Uani 1 1 d . . . O8 O -0.0051(2) 0.34021(19) 0.7318(2) 0.0308(6) Uani 1 1 d . . . O7 O -0.0954(2) 0.1575(2) 0.69764(19) 0.0294(6) Uani 1 1 d . . . O9 O 0.0905(2) 0.1669(2) 0.78809(19) 0.0282(6) Uani 1 1 d . . . N1 N 0.1987(2) 0.4658(2) 0.5423(2) 0.0166(5) Uani 1 1 d . . . N2 N 0.2713(2) 0.4692(2) 0.8213(2) 0.0157(5) Uani 1 1 d . . . H1N2 H 0.234(3) 0.531(3) 0.835(3) 0.024 Uiso 1 1 d . . . N3 N 0.1926(2) 0.4909(2) 1.10426(19) 0.0141(5) Uani 1 1 d . . . H1N3 H 0.218(3) 0.465(3) 1.159(3) 0.021 Uiso 1 1 d . . . N4 N 0.2793(2) 0.7858(2) 1.12451(19) 0.0143(5) Uani 1 1 d . . . C1 C 0.1149(3) 0.6065(3) 0.6755(3) 0.0177(6) Uani 1 1 d . . . H1A H 0.0747 0.6401 0.6125 0.027 Uiso 1 1 calc R . . H1B H 0.1652 0.6647 0.7100 0.027 Uiso 1 1 calc R . . H1C H 0.0562 0.5797 0.7271 0.027 Uiso 1 1 calc R . . C2 C 0.1901(3) 0.5063(2) 0.6400(2) 0.0147(6) Uani 1 1 d . . . C3 C 0.2634(3) 0.4337(2) 0.7187(2) 0.0142(6) Uani 1 1 d . . . C4 C 0.3323(3) 0.4053(2) 0.9097(2) 0.0164(6) Uani 1 1 d . . . H4A H 0.3716 0.4604 0.9593 0.020 Uiso 1 1 calc R . . H4B H 0.3937 0.3551 0.8787 0.020 Uiso 1 1 calc R . . C5 C 0.2432(3) 0.3306(2) 0.9741(2) 0.0173(6) Uani 1 1 d . . . H5A H 0.2865 0.2883 1.0315 0.021 Uiso 1 1 calc R . . H5B H 0.2069 0.2734 0.9248 0.021 Uiso 1 1 calc R . . C6 C 0.1431(3) 0.4038(2) 1.0268(2) 0.0165(6) Uani 1 1 d . . . H6A H 0.0973 0.4437 0.9694 0.020 Uiso 1 1 calc R . . H6B H 0.0887 0.3522 1.0656 0.020 Uiso 1 1 calc R . . C7 C 0.2105(3) 0.6017(2) 1.0788(2) 0.0140(6) Uani 1 1 d . . . C8 C 0.2732(3) 0.6787(2) 1.1604(2) 0.0141(6) Uani 1 1 d . . . C9 C 0.3261(3) 0.6381(3) 1.2669(2) 0.0196(7) Uani 1 1 d . . . H9A H 0.3952 0.6851 1.2852 0.029 Uiso 1 1 calc R . . H9B H 0.3499 0.5576 1.2604 0.029 Uiso 1 1 calc R . . H9C H 0.2673 0.6455 1.3237 0.029 Uiso 1 1 calc R . . 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 0.0305(2) 0.01222(19) 0.01077(19) -0.00082(14) -0.00016(15) 0.00460(16) Cl1 0.0163(4) 0.0170(4) 0.0175(4) -0.0005(3) 0.0024(3) -0.0014(3) O1 0.0316(13) 0.0177(11) 0.0118(10) 0.0034(9) -0.0006(9) 0.0048(10) O2 0.0238(12) 0.0128(10) 0.0131(10) -0.0019(8) 0.0019(9) 0.0024(9) O3 0.0202(11) 0.0117(10) 0.0100(10) 0.0002(8) -0.0009(8) -0.0005(8) O4 0.0252(11) 0.0156(11) 0.0121(10) -0.0048(8) 0.0019(9) -0.0058(9) O5 0.0323(14) 0.0486(17) 0.0301(14) -0.0135(12) 0.0081(12) -0.0102(13) O6 0.0332(14) 0.0312(14) 0.0207(12) -0.0044(10) 0.0131(11) -0.0078(11) O8 0.0405(15) 0.0176(12) 0.0347(14) -0.0001(10) 0.0140(12) 0.0011(10) O7 0.0219(12) 0.0368(14) 0.0295(13) -0.0029(11) 0.0019(11) -0.0137(10) O9 0.0252(13) 0.0342(14) 0.0250(12) -0.0011(10) -0.0039(10) 0.0102(10) N1 0.0219(13) 0.0130(12) 0.0149(13) 0.0036(10) 0.0007(11) -0.0001(11) N2 0.0232(14) 0.0108(12) 0.0133(12) 0.0000(10) 0.0022(11) 0.0004(10) N3 0.0205(14) 0.0132(12) 0.0087(12) 0.0002(10) 0.0002(10) 0.0018(10) N4 0.0157(12) 0.0147(13) 0.0126(12) -0.0033(9) 0.0027(10) -0.0025(10) C1 0.0205(16) 0.0139(14) 0.0187(15) -0.0001(12) 0.0005(13) 0.0010(13) C2 0.0177(15) 0.0121(14) 0.0144(14) 0.0009(11) 0.0023(12) -0.0034(12) C3 0.0179(15) 0.0099(13) 0.0148(14) 0.0001(11) 0.0050(12) -0.0034(11) C4 0.0225(16) 0.0143(15) 0.0123(14) -0.0010(11) -0.0003(13) 0.0013(12) C5 0.0266(17) 0.0124(15) 0.0128(14) -0.0005(11) 0.0023(13) -0.0013(12) C6 0.0226(16) 0.0120(14) 0.0150(14) -0.0012(11) 0.0022(13) -0.0012(12) C7 0.0152(14) 0.0140(14) 0.0129(14) 0.0004(11) 0.0054(12) 0.0009(12) C8 0.0195(15) 0.0116(14) 0.0112(13) -0.0003(11) 0.0054(12) 0.0019(12) C9 0.0248(17) 0.0176(15) 0.0165(15) -0.0009(12) -0.0012(13) 0.0010(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 N4 1.949(2) 2_546 ? Cu1 N1 1.973(2) . ? Cu1 O3 1.988(2) 2_546 ? Cu1 O2 1.992(2) . ? Cu1 O5 2.336(3) . ? Cl1 O7 1.426(2) . ? Cl1 O8 1.437(2) . ? Cl1 O6 1.445(2) . ? Cl1 O9 1.447(2) . ? O1 N1 1.363(3) . ? O1 H1O1 0.93(4) . ? O2 C3 1.269(3) . ? O3 C7 1.274(3) . ? O3 Cu1 1.988(2) 2_556 ? O4 N4 1.328(3) . ? O5 H105 0.9158 . ? O5 H205 0.8631 . ? N1 C2 1.278(4) . ? N2 C3 1.312(4) . ? N2 C4 1.457(4) . ? N2 H1N2 0.83(3) . ? N3 C7 1.317(4) . ? N3 C6 1.469(4) . ? N3 H1N3 0.78(3) . ? N4 C8 1.299(4) . ? N4 Cu1 1.949(2) 2_556 ? C1 C2 1.483(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.496(4) . ? C4 C5 1.528(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.537(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.490(4) . ? C8 C9 1.486(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 N4 Cu1 N1 95.20(10) 2_546 . ? N4 Cu1 O3 81.95(9) 2_546 2_546 ? N1 Cu1 O3 167.01(9) . 2_546 ? N4 Cu1 O2 172.28(9) 2_546 . ? N1 Cu1 O2 80.72(9) . . ? O3 Cu1 O2 100.56(8) 2_546 . ? N4 Cu1 O5 99.25(10) 2_546 . ? N1 Cu1 O5 99.28(10) . . ? O3 Cu1 O5 93.69(9) 2_546 . ? O2 Cu1 O5 87.91(9) . . ? O7 Cl1 O8 110.15(15) . . ? O7 Cl1 O6 109.79(14) . . ? O8 Cl1 O6 110.75(14) . . ? O7 Cl1 O9 108.21(14) . . ? O8 Cl1 O9 108.60(14) . . ? O6 Cl1 O9 109.29(15) . . ? N1 O1 H1O1 105(2) . . ? C3 O2 Cu1 111.57(18) . . ? C7 O3 Cu1 111.24(18) . 2_556 ? Cu1 O5 H105 118.5 . . ? Cu1 O5 H205 121.6 . . ? H105 O5 H205 119.8 . . ? C2 N1 O1 117.7(2) . . ? C2 N1 Cu1 117.1(2) . . ? O1 N1 Cu1 124.44(18) . . ? C3 N2 C4 124.7(3) . . ? C3 N2 H1N2 115(2) . . ? C4 N2 H1N2 120(2) . . ? C7 N3 C6 123.7(2) . . ? C7 N3 H1N3 121(3) . . ? C6 N3 H1N3 114(3) . . ? C8 N4 O4 120.4(2) . . ? C8 N4 Cu1 116.29(19) . 2_556 ? O4 N4 Cu1 123.13(18) . 2_556 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 126.8(3) . . ? N1 C2 C3 110.2(3) . . ? C1 C2 C3 123.0(3) . . ? O2 C3 N2 122.7(3) . . ? O2 C3 C2 119.6(2) . . ? N2 C3 C2 117.6(3) . . ? N2 C4 C5 110.9(2) . . ? N2 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 112.8(2) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N3 C6 C5 111.5(2) . . ? N3 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? O3 C7 N3 122.0(3) . . ? O3 C7 C8 119.3(3) . . ? N3 C7 C8 118.7(3) . . ? N4 C8 C9 124.2(3) . . ? N4 C8 C7 111.0(2) . . ? C9 C8 C7 124.8(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 N1 Cu1 O2 C3 5.23(19) . . . . ? O3 Cu1 O2 C3 -161.65(19) 2_546 . . . ? O5 Cu1 O2 C3 105.0(2) . . . . ? N4 Cu1 N1 C2 164.7(2) 2_546 . . . ? O3 Cu1 N1 C2 88.1(5) 2_546 . . . ? O2 Cu1 N1 C2 -8.7(2) . . . . ? O5 Cu1 N1 C2 -95.0(2) . . . . ? N4 Cu1 N1 O1 -4.9(2) 2_546 . . . ? O3 Cu1 N1 O1 -81.6(5) 2_546 . . . ? O2 Cu1 N1 O1 -178.3(2) . . . . ? O5 Cu1 N1 O1 95.3(2) . . . . ? O1 N1 C2 C1 2.8(4) . . . . ? Cu1 N1 C2 C1 -167.6(2) . . . . ? O1 N1 C2 C3 179.9(2) . . . . ? Cu1 N1 C2 C3 9.5(3) . . . . ? Cu1 O2 C3 N2 178.2(2) . . . . ? Cu1 O2 C3 C2 -1.8(3) . . . . ? C4 N2 C3 O2 -4.2(5) . . . . ? C4 N2 C3 C2 175.9(3) . . . . ? N1 C2 C3 O2 -5.0(4) . . . . ? C1 C2 C3 O2 172.2(3) . . . . ? N1 C2 C3 N2 175.0(3) . . . . ? C1 C2 C3 N2 -7.8(4) . . . . ? C3 N2 C4 C5 -95.6(3) . . . . ? N2 C4 C5 C6 -59.6(3) . . . . ? C7 N3 C6 C5 98.0(3) . . . . ? C4 C5 C6 N3 -59.8(3) . . . . ? Cu1 O3 C7 N3 -179.0(2) 2_556 . . . ? Cu1 O3 C7 C8 -0.3(3) 2_556 . . . ? C6 N3 C7 O3 5.1(4) . . . . ? C6 N3 C7 C8 -173.6(3) . . . . ? O4 N4 C8 C9 -2.6(4) . . . . ? Cu1 N4 C8 C9 172.4(2) 2_556 . . . ? O4 N4 C8 C7 179.6(2) . . . . ? Cu1 N4 C8 C7 -5.5(3) 2_556 . . . ? O3 C7 C8 N4 3.8(4) . . . . ? N3 C7 C8 N4 -177.4(3) . . . . ? O3 C7 C8 C9 -174.0(3) . . . . ? N3 C7 C8 C9 4.8(4) . . . . ? 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 O1 H1O1 O4 0.93(4) 1.60(4) 2.517(3) 166(3) 2_546 N2 H1N2 O3 0.83(3) 2.33(3) 3.016(3) 139(3) . N3 H1N3 O4 0.78(3) 2.26(3) 2.923(3) 144(3) 2_547 _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.864 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.091 # Attachment '- 2b.cif' data_2b _database_code_depnum_ccdc_archive 'CCDC 764189' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H68 Cu4 N20 O30, 4(C H Cl3)' _chemical_formula_sum 'C42 H72 Cl12 Cu4 N20 O30' _chemical_formula_weight 2016.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.9996(2) _cell_length_b 25.7141(5) _cell_length_c 17.1427(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.5420(12) _cell_angle_gamma 90.00 _cell_volume 3963.20(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11831 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 1.552 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7099 _exptl_absorpt_correction_T_max 0.8309 _exptl_absorpt_process_details 'SADABS-2008/1 (Sheldrick, 2008)' _publ_section_exptl_refinement ; One of the chloroform molecules was disordered over two sites wit occupancies 0.73/0.27. The C-Cl and Cl...Cl distances were set to be equal. Furthermore, the carbon atoms in the disordered chloroform molecules were restrained with effective standard deviation 0.01 so that its U~ij~ components approximate to isotropic behavior. The OH and NH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.44 \%A from atom Cl3 and the deepest hole is located 0.56 \%A from atom Cl3. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32836 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7772 _reflns_number_gt 5906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2008)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0889P)^2^+18.6674P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7772 _refine_ls_number_parameters 512 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1631 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.046 _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 Cu1 Cu 0.18532(7) 0.41579(2) 0.43593(4) 0.01892(17) Uani 1 1 d . . . Cu2 Cu 0.15485(7) 0.43195(2) 0.03221(4) 0.02060(18) Uani 1 1 d . . . Cl1 Cl 0.4244(2) 0.35948(9) 0.21140(12) 0.0614(5) Uani 1 1 d . . . Cl2 Cl 0.71914(19) 0.38503(8) 0.27080(12) 0.0544(5) Uani 1 1 d . . . Cl3 Cl 0.5492(3) 0.31235(10) 0.35512(14) 0.0740(6) Uani 1 1 d . . . O1 O -0.0093(4) 0.39160(14) 0.5656(2) 0.0269(8) Uani 1 1 d D . . H1O H 0.0310 0.4209 0.5771 0.040 Uiso 1 1 d RD . . O2 O 0.1822(4) 0.35073(13) 0.3747(2) 0.0229(8) Uani 1 1 d . . . O3 O 0.3368(4) 0.45693(13) 0.3816(2) 0.0196(7) Uani 1 1 d . . . O4 O 0.1192(4) 0.47772(13) 0.5709(2) 0.0240(8) Uani 1 1 d . . . O5 O 0.0085(4) 0.44527(14) 0.3470(2) 0.0244(8) Uani 1 1 d . . . H5O H -0.0351 0.4692 0.3710 0.029(16) Uiso 1 1 d R . . O6 O 0.3789(5) 0.38280(14) 0.5367(3) 0.0418(11) Uani 1 1 d . . . O8 O 0.5659(6) 0.3335(2) 0.5540(5) 0.083(2) Uani 1 1 d . . . O7 O 0.3504(5) 0.29924(14) 0.5327(3) 0.0393(11) Uani 1 1 d . . . O1A O -0.0595(4) 0.42085(13) -0.1001(2) 0.0235(8) Uani 1 1 d . . . H1P H -0.0080 0.4494 -0.1045 0.035 Uiso 1 1 d R . . O2A O 0.1341(4) 0.36800(13) 0.0917(2) 0.0234(8) Uani 1 1 d . . . O3A O 0.3047(4) 0.46722(13) 0.0986(2) 0.0208(7) Uani 1 1 d . . . O4A O 0.0835(4) 0.50451(14) -0.0933(2) 0.0243(8) Uani 1 1 d . . . O5A O 0.3450(4) 0.39069(14) -0.0440(2) 0.0305(9) Uani 1 1 d . . . O6A O 0.4969(4) 0.33056(15) -0.0781(3) 0.0339(9) Uani 1 1 d . . . O7A O 0.2655(5) 0.31199(15) -0.0644(3) 0.0433(12) Uani 1 1 d . . . N1 N 0.0491(5) 0.37479(16) 0.4989(2) 0.0204(9) Uani 1 1 d D . . N2 N 0.1952(4) 0.47605(16) 0.5057(2) 0.0194(9) Uani 1 1 d . . . N3 N 0.4291(5) 0.33799(18) 0.5407(3) 0.0305(11) Uani 1 1 d . . . N4 N 0.0760(5) 0.27167(16) 0.3683(3) 0.0246(10) Uani 1 1 d . . . H4N H 0.0268 0.2476 0.3889 0.037 Uiso 1 1 d R . . N5 N 0.4528(5) 0.53468(16) 0.3882(2) 0.0206(9) Uani 1 1 d . . . H5 H 0.4613 0.5652 0.4105 0.031 Uiso 1 1 d R . . N6 N 0.0381(5) 0.28709(16) 0.0806(3) 0.0233(9) Uani 1 1 d . . . H6 H -0.0296 0.2607 0.0599 0.035 Uiso 1 1 d R . . N7 N 0.4576(5) 0.53652(16) 0.0991(2) 0.0200(9) Uani 1 1 d . . . H7 H 0.4819 0.5674 0.0728 0.030 Uiso 1 1 d R . . N8 N 0.0017(4) 0.39901(16) -0.0346(2) 0.0201(9) Uani 1 1 d . . . N9 N 0.1702(4) 0.49489(16) -0.0300(2) 0.0186(9) Uani 1 1 d . . . N10 N 0.3681(5) 0.34354(16) -0.0626(3) 0.0260(10) Uani 1 1 d . . . C1 C 0.0987(6) 0.3169(2) 0.4022(3) 0.0229(11) Uani 1 1 d . . . C2 C 0.0198(6) 0.3288(2) 0.4760(3) 0.0244(11) Uani 1 1 d . . . C3 C -0.0786(8) 0.2912(2) 0.5155(4) 0.0426(16) Uani 1 1 d . . . H3A H -0.1199 0.3078 0.5612 0.064 Uiso 1 1 calc R . . H3B H -0.0206 0.2606 0.5321 0.064 Uiso 1 1 calc R . . H3C H -0.1599 0.2805 0.4790 0.064 Uiso 1 1 calc R . . C4 C 0.2799(5) 0.51386(18) 0.4868(3) 0.0185(10) Uani 1 1 d . . . C5 C 0.3013(6) 0.56402(19) 0.5295(3) 0.0234(11) Uani 1 1 d . . . H5A H 0.2401 0.5642 0.5754 0.035 Uiso 1 1 calc R . . H5B H 0.2715 0.5929 0.4950 0.035 Uiso 1 1 calc R . . H5C H 0.4062 0.5679 0.5462 0.035 Uiso 1 1 calc R . . C6 C 0.3590(5) 0.50071(19) 0.4142(3) 0.0182(10) Uani 1 1 d . . . C7 C 0.1420(6) 0.2592(2) 0.2946(3) 0.0242(11) Uani 1 1 d . . . H7A H 0.1438 0.2210 0.2877 0.029 Uiso 1 1 calc R . . H7B H 0.2460 0.2719 0.2958 0.029 Uiso 1 1 calc R . . C8 C 0.0550(6) 0.2839(2) 0.2256(3) 0.0271(12) Uani 1 1 d . . . H8A H 0.0563 0.3222 0.2311 0.032 Uiso 1 1 calc R . . H8B H -0.0498 0.2722 0.2251 0.032 Uiso 1 1 calc R . . C9 C 0.1243(6) 0.2684(2) 0.1493(3) 0.0248(11) Uani 1 1 d . . . H9A H 0.2263 0.2827 0.1486 0.030 Uiso 1 1 calc R . . H9B H 0.1317 0.2300 0.1468 0.030 Uiso 1 1 calc R . . C10 C 0.5369(6) 0.5250(2) 0.3184(3) 0.0214(11) Uani 1 1 d . . . H10A H 0.5676 0.4880 0.3177 0.026 Uiso 1 1 calc R . . H10B H 0.6282 0.5465 0.3209 0.026 Uiso 1 1 calc R . . C11 C 0.4477(6) 0.5373(2) 0.2433(3) 0.0231(11) Uani 1 1 d . . . H11A H 0.3525 0.5179 0.2423 0.028 Uiso 1 1 calc R . . H11B H 0.4246 0.5749 0.2413 0.028 Uiso 1 1 calc R . . C12 C 0.5347(6) 0.5223(2) 0.1729(3) 0.0216(11) Uani 1 1 d . . . H12A H 0.6328 0.5397 0.1764 0.026 Uiso 1 1 calc R . . H12B H 0.5521 0.4843 0.1736 0.026 Uiso 1 1 calc R . . C13 C 0.0526(6) 0.3354(2) 0.0554(3) 0.0219(11) Uani 1 1 d . . . C14 C -0.0295(5) 0.35155(19) -0.0183(3) 0.0214(11) Uani 1 1 d . . . C15 C -0.1274(7) 0.3165(2) -0.0676(4) 0.0341(14) Uani 1 1 d . . . H15A H -0.1895 0.3374 -0.1040 0.051 Uiso 1 1 calc R . . H15B H -0.1911 0.2962 -0.0340 0.051 Uiso 1 1 calc R . . H15C H -0.0657 0.2928 -0.0971 0.051 Uiso 1 1 calc R . . C16 C 0.2742(5) 0.52716(19) -0.0073(3) 0.0183(10) Uani 1 1 d . . . C17 C 0.3153(6) 0.5759(2) -0.0472(3) 0.0232(11) Uani 1 1 d . . . H17A H 0.2473 0.5816 -0.0926 0.035 Uiso 1 1 calc R . . H17B H 0.4174 0.5731 -0.0644 0.035 Uiso 1 1 calc R . . H17C H 0.3084 0.6052 -0.0110 0.035 Uiso 1 1 calc R . . C18 C 0.3484(5) 0.50868(18) 0.0674(3) 0.0183(10) Uani 1 1 d . . . C19 C 0.0419(7) 0.4588(3) 0.2687(4) 0.0401(15) Uani 1 1 d . . . H19A H 0.0974 0.4916 0.2689 0.060 Uiso 1 1 calc R . . H19B H -0.0509 0.4628 0.2372 0.060 Uiso 1 1 calc R . . H19C H 0.1022 0.4312 0.2464 0.060 Uiso 1 1 calc R . . C20 C 0.5382(8) 0.3652(3) 0.2942(5) 0.0527(18) Uani 1 1 d . . . H20 H 0.4963 0.3942 0.3253 0.063 Uiso 1 1 calc R . . C21 C 0.6942(14) 0.1620(7) 0.206(2) 0.162(11) Uani 0.731(4) 1 d PDU A 1 H21 H 0.6902 0.1496 0.1505 0.194 Uiso 0.731(4) 1 calc PR A 1 Cl4 Cl 0.8774(3) 0.16068(8) 0.23577(14) 0.0459(7) Uani 0.731(4) 1 d PD A 1 Cl5 Cl 0.5906(3) 0.11811(18) 0.2566(2) 0.0780(12) Uani 0.731(4) 1 d PD A 1 Cl6 Cl 0.6226(4) 0.22476(12) 0.2030(2) 0.0782(11) Uani 0.731(4) 1 d PD A 1 C21B C 0.573(2) 0.1375(7) 0.244(3) 0.080(2) Uani 0.269(4) 1 d PDU A 2 H21B H 0.5959 0.1444 0.3009 0.096 Uiso 0.269(4) 1 calc PR A 2 Cl4B Cl 0.7118(13) 0.1637(4) 0.2044(7) 0.080(2) Uani 0.269(4) 1 d PD A 2 Cl5B Cl 0.4178(11) 0.1664(4) 0.2307(5) 0.080(2) Uani 0.269(4) 1 d PD A 2 Cl6B Cl 0.5817(12) 0.0751(4) 0.2406(5) 0.080(2) Uani 0.269(4) 1 d PD A 2 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 0.0204(3) 0.0160(3) 0.0205(3) -0.0017(2) 0.0024(2) -0.0017(2) Cu2 0.0224(3) 0.0212(3) 0.0179(3) 0.0014(2) -0.0032(2) -0.0068(2) Cl1 0.0479(10) 0.0861(14) 0.0489(11) 0.0109(10) -0.0139(8) -0.0137(10) Cl2 0.0387(9) 0.0632(11) 0.0611(11) -0.0102(9) 0.0004(8) -0.0192(8) Cl3 0.0789(15) 0.0790(15) 0.0635(14) 0.0196(11) -0.0041(11) -0.0066(12) O1 0.032(2) 0.0263(19) 0.0232(19) -0.0038(15) 0.0053(16) -0.0044(16) O2 0.0235(18) 0.0187(17) 0.0269(19) -0.0010(15) 0.0035(15) -0.0021(14) O3 0.0208(18) 0.0181(17) 0.0200(18) -0.0033(14) 0.0002(14) -0.0013(14) O4 0.030(2) 0.0219(18) 0.0205(18) -0.0029(15) 0.0070(15) 0.0017(15) O5 0.028(2) 0.0252(19) 0.0200(19) -0.0009(15) 0.0005(15) 0.0062(15) O6 0.035(2) 0.0177(19) 0.070(3) -0.005(2) -0.021(2) 0.0037(17) O8 0.042(3) 0.059(4) 0.149(7) 0.053(4) -0.001(4) 0.001(3) O7 0.044(2) 0.0152(19) 0.057(3) -0.0033(18) -0.018(2) 0.0006(17) O1A 0.0234(19) 0.0223(18) 0.0243(19) -0.0010(15) -0.0055(15) 0.0010(14) O2A 0.0266(19) 0.0206(18) 0.0226(19) -0.0003(15) -0.0031(15) -0.0080(15) O3A 0.0235(18) 0.0203(18) 0.0183(18) 0.0014(14) -0.0024(14) -0.0030(14) O4A 0.0269(19) 0.0275(19) 0.0179(18) 0.0028(15) -0.0057(15) -0.0006(15) O5A 0.029(2) 0.0165(18) 0.047(2) 0.0012(17) 0.0165(18) 0.0002(15) O6A 0.025(2) 0.029(2) 0.048(3) -0.0077(19) 0.0060(18) 0.0051(16) O7A 0.033(2) 0.020(2) 0.078(3) 0.001(2) 0.012(2) -0.0044(17) N1 0.021(2) 0.022(2) 0.018(2) -0.0020(17) -0.0014(17) 0.0020(17) N2 0.019(2) 0.021(2) 0.019(2) 0.0010(17) 0.0020(17) 0.0044(17) N3 0.030(3) 0.025(2) 0.036(3) 0.008(2) -0.002(2) 0.006(2) N4 0.036(3) 0.015(2) 0.023(2) -0.0006(18) 0.0023(19) -0.0065(18) N5 0.025(2) 0.019(2) 0.018(2) -0.0020(17) 0.0005(18) -0.0025(17) N6 0.027(2) 0.018(2) 0.025(2) 0.0001(18) -0.0011(19) -0.0054(17) N7 0.020(2) 0.021(2) 0.020(2) 0.0013(17) 0.0018(17) -0.0040(17) N8 0.016(2) 0.025(2) 0.019(2) -0.0016(18) 0.0009(17) 0.0023(17) N9 0.019(2) 0.022(2) 0.014(2) -0.0011(17) -0.0010(16) 0.0028(17) N10 0.025(2) 0.019(2) 0.034(3) 0.0038(19) 0.003(2) 0.0011(18) C1 0.026(3) 0.023(3) 0.020(3) 0.001(2) -0.003(2) 0.001(2) C2 0.026(3) 0.025(3) 0.022(3) 0.003(2) -0.001(2) -0.005(2) C3 0.061(4) 0.030(3) 0.038(4) -0.003(3) 0.015(3) -0.017(3) C4 0.020(2) 0.018(2) 0.017(2) -0.0005(19) -0.001(2) 0.0022(19) C5 0.025(3) 0.020(3) 0.025(3) -0.002(2) 0.002(2) 0.001(2) C6 0.017(2) 0.019(2) 0.018(2) 0.001(2) -0.0031(19) 0.0033(19) C7 0.032(3) 0.018(2) 0.023(3) -0.005(2) 0.001(2) -0.001(2) C8 0.034(3) 0.022(3) 0.025(3) 0.000(2) 0.000(2) -0.002(2) C9 0.030(3) 0.020(2) 0.024(3) 0.000(2) -0.001(2) -0.003(2) C10 0.022(3) 0.022(3) 0.020(3) -0.001(2) 0.002(2) -0.002(2) C11 0.020(3) 0.030(3) 0.019(3) -0.001(2) 0.000(2) -0.004(2) C12 0.020(3) 0.025(3) 0.019(3) 0.000(2) -0.002(2) -0.004(2) C13 0.021(3) 0.024(3) 0.021(3) -0.003(2) 0.002(2) -0.002(2) C14 0.017(2) 0.022(3) 0.025(3) -0.006(2) -0.002(2) 0.003(2) C15 0.033(3) 0.023(3) 0.045(4) -0.012(3) -0.011(3) -0.001(2) C16 0.020(2) 0.021(2) 0.014(2) -0.0041(19) 0.0010(19) 0.003(2) C17 0.022(3) 0.023(3) 0.025(3) 0.003(2) 0.003(2) 0.003(2) C18 0.020(2) 0.017(2) 0.018(2) -0.001(2) 0.0033(19) 0.0015(19) C19 0.038(4) 0.054(4) 0.029(3) 0.000(3) 0.004(3) -0.003(3) C20 0.042(4) 0.066(5) 0.050(4) -0.007(4) 0.002(3) -0.005(3) C21 0.165(14) 0.151(13) 0.169(14) -0.006(9) 0.023(9) -0.018(9) Cl4 0.0558(15) 0.0319(11) 0.0486(14) 0.0005(9) -0.0141(11) -0.0088(10) Cl5 0.0611(18) 0.126(4) 0.0470(18) 0.029(2) 0.0037(14) -0.0372(19) Cl6 0.072(2) 0.0651(19) 0.096(2) -0.0187(17) -0.0078(18) 0.0251(15) C21B 0.109(4) 0.086(4) 0.047(3) 0.001(2) 0.024(3) 0.031(3) Cl4B 0.109(4) 0.086(4) 0.047(3) 0.001(2) 0.024(3) 0.031(3) Cl5B 0.109(4) 0.086(4) 0.047(3) 0.001(2) 0.024(3) 0.031(3) Cl6B 0.109(4) 0.086(4) 0.047(3) 0.001(2) 0.024(3) 0.031(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.956(4) . yes Cu1 N1 1.974(4) . yes Cu1 O2 1.975(3) . yes Cu1 O3 1.989(3) . yes Cu1 O5 2.284(4) . yes Cu2 N9 1.947(4) . yes Cu2 N8 1.947(4) . yes Cu2 O2A 1.948(3) . yes Cu2 O3A 1.949(3) . yes Cu2 O4A 2.927(4) 3_565 yes Cl1 C20 1.719(8) . ? Cl2 C20 1.769(7) . ? Cl3 C20 1.714(8) . ? O1 N1 1.350(5) . ? O1 H1O 0.8548 . ? O2 C1 1.256(6) . ? O3 C6 1.268(6) . ? O4 N2 1.337(5) . ? O5 C19 1.431(7) . ? O5 H5O 0.8453 . ? O6 N3 1.238(6) . ? O8 N3 1.247(7) . ? O7 N3 1.227(6) . ? O1A N8 1.351(6) . ? O1A H1P 0.8734 . ? O2A C13 1.259(6) . ? O3A C18 1.263(6) . ? O4A N9 1.331(5) . ? O5A N10 1.273(6) . ? O6A N10 1.246(6) . ? O7A N10 1.228(6) . ? N1 C2 1.270(7) . ? N2 C4 1.286(6) . ? N4 C1 1.311(7) . ? N4 C7 1.455(7) . ? N4 H4N 0.8467 . ? N5 C6 1.306(6) . ? N5 C10 1.466(6) . ? N5 H5 0.8750 . ? N6 C13 1.325(7) . ? N6 C9 1.461(7) . ? N6 H6 0.9692 . ? N7 C18 1.314(6) . ? N7 C12 1.461(7) . ? N7 H7 0.9445 . ? N8 C14 1.286(7) . ? N9 C16 1.298(6) . ? C1 C2 1.509(7) . ? C2 C3 1.494(8) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.492(7) . ? C4 C6 1.500(7) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C7 C8 1.527(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.528(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.494(7) . ? C14 C15 1.496(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.483(7) . ? C16 C18 1.494(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20 1.0000 . ? C21 Cl4 1.705(17) . ? C21 Cl5 1.723(16) . ? C21 Cl6 1.738(16) . ? C21 H21 1.0000 . ? C21B Cl5B 1.586(17) . ? C21B Cl4B 1.602(17) . ? C21B Cl6B 1.607(17) . ? C21B H21B 1.0000 . ? 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 N2 Cu1 N1 95.81(16) . . ? N2 Cu1 O2 174.25(16) . . ? N1 Cu1 O2 81.02(15) . . ? N2 Cu1 O3 81.45(15) . . ? N1 Cu1 O3 174.28(16) . . ? O2 Cu1 O3 101.28(14) . . ? N2 Cu1 O5 99.00(15) . . ? N1 Cu1 O5 96.38(15) . . ? O2 Cu1 O5 86.16(14) . . ? O3 Cu1 O5 89.02(14) . . ? N9 Cu2 N8 96.02(17) . . ? N9 Cu2 O2A 177.89(16) . . ? N8 Cu2 O2A 81.87(16) . . ? N9 Cu2 O3A 82.47(15) . . ? N8 Cu2 O3A 178.03(16) . . ? O2A Cu2 O3A 99.63(14) . . ? N1 O1 H1O 107.5 . . ? C1 O2 Cu1 112.5(3) . . ? C6 O3 Cu1 111.4(3) . . ? C19 O5 Cu1 122.5(3) . . ? C19 O5 H5O 113.7 . . ? Cu1 O5 H5O 103.9 . . ? N8 O1A H1P 102.8 . . ? C13 O2A Cu2 111.7(3) . . ? C18 O3A Cu2 111.5(3) . . ? C2 N1 O1 118.5(4) . . ? C2 N1 Cu1 117.0(3) . . ? O1 N1 Cu1 124.5(3) . . ? C4 N2 O4 121.2(4) . . ? C4 N2 Cu1 117.1(3) . . ? O4 N2 Cu1 121.7(3) . . ? O7 N3 O6 122.8(5) . . ? O7 N3 O8 120.4(5) . . ? O6 N3 O8 116.8(5) . . ? C1 N4 C7 121.2(4) . . ? C1 N4 H4N 122.5 . . ? C7 N4 H4N 116.2 . . ? C6 N5 C10 121.9(4) . . ? C6 N5 H5 119.8 . . ? C10 N5 H5 118.1 . . ? C13 N6 C9 121.0(4) . . ? C13 N6 H6 127.3 . . ? C9 N6 H6 111.6 . . ? C18 N7 C12 122.6(4) . . ? C18 N7 H7 116.4 . . ? C12 N7 H7 120.9 . . ? C14 N8 O1A 119.4(4) . . ? C14 N8 Cu2 116.2(4) . . ? O1A N8 Cu2 124.1(3) . . ? C16 N9 O4A 121.0(4) . . ? C16 N9 Cu2 115.8(3) . . ? O4A N9 Cu2 123.2(3) . . ? O7A N10 O6A 121.5(4) . . ? O7A N10 O5A 120.3(4) . . ? O6A N10 O5A 118.2(4) . . ? O2 C1 N4 122.1(5) . . ? O2 C1 C2 119.0(4) . . ? N4 C1 C2 118.9(5) . . ? N1 C2 C3 125.6(5) . . ? N1 C2 C1 110.5(4) . . ? C3 C2 C1 123.9(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C5 126.5(5) . . ? N2 C4 C6 110.3(4) . . ? C5 C4 C6 123.2(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 N5 122.4(4) . . ? O3 C6 C4 119.6(4) . . ? N5 C6 C4 118.0(4) . . ? N4 C7 C8 111.4(4) . . ? N4 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N4 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 109.9(4) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N6 C9 C8 112.4(4) . . ? N6 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? N6 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N5 C10 C11 112.6(4) . . ? N5 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N5 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 110.4(4) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N7 C12 C11 112.6(4) . . ? N7 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? N7 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? O2A C13 N6 121.8(5) . . ? O2A C13 C14 119.3(5) . . ? N6 C13 C14 119.0(4) . . ? N8 C14 C13 110.0(4) . . ? N8 C14 C15 125.3(5) . . ? C13 C14 C15 124.6(5) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N9 C16 C17 126.4(5) . . ? N9 C16 C18 110.1(4) . . ? C17 C16 C18 123.5(4) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3A C18 N7 121.7(5) . . ? O3A C18 C16 119.6(4) . . ? N7 C18 C16 118.6(4) . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? Cl3 C20 Cl1 116.8(5) . . ? Cl3 C20 Cl2 109.7(4) . . ? Cl1 C20 Cl2 111.0(4) . . ? Cl3 C20 H20 106.2 . . ? Cl1 C20 H20 106.2 . . ? Cl2 C20 H20 106.2 . . ? Cl4 C21 Cl5 111.9(13) . . ? Cl4 C21 Cl6 112.2(13) . . ? Cl5 C21 Cl6 114.5(14) . . ? Cl4 C21 H21 105.8 . . ? Cl5 C21 H21 105.8 . . ? Cl6 C21 H21 105.8 . . ? Cl5B C21B Cl4B 116.1(14) . . ? Cl5B C21B Cl6B 120.5(16) . . ? Cl4B C21B Cl6B 111.1(14) . . ? Cl5B C21B H21B 101.8 . . ? Cl4B C21B H21B 101.8 . . ? Cl6B C21B H21B 101.8 . . ? 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 _geom_hbond_publ_flag O1 H1O O4 0.85 1.67 2.498(5) 162.7 . yes O5 H5O O4 0.85 1.87 2.714(5) 175.8 3_566 yes O1A H1P O4A 0.87 1.65 2.507(5) 168.1 . yes N4 H4N O6A 0.85 2.11 2.884(6) 152.1 4_566 yes N5 H5 O6 0.87 2.13 2.877(6) 142.3 3_666 yes N6 H6 O7 0.97 1.93 2.887(6) 170.1 4_565 yes N7 H7 O5A 0.94 1.97 2.775(5) 141.3 3_665 yes _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.254 _refine_diff_density_min -1.058 _refine_diff_density_rms 0.130 # Attachment '- 4a.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 764190' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H50 Cu2 N10 O16, C H4 O, 2(C H4 O)' _chemical_formula_sum 'C29 H62 Cu2 N10 O19' _chemical_formula_weight 981.97 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2339(6) _cell_length_b 11.8198(8) _cell_length_c 13.0453(8) _cell_angle_alpha 67.567(4) _cell_angle_beta 75.501(5) _cell_angle_gamma 71.766(5) _cell_volume 1102.13(13) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13004 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 1.048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7284 _exptl_absorpt_correction_T_max 0.7939 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _publ_section_exptl_refinement ; Both methanol molecules were disordered over two sites with occupancy ratios 0.50/0.50 and 0.51/0.49 respectively. The OH hydrogen H98 was shared by oxygens O97 and O98. Similarly, the OH hydrogen atom H1O was alternatively bonded to O1 or O4. Therefore the apparent O1-H10 bond was unusually long and the n on-bonding distance O4...H10 too short. The OH and NH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.37 \%A from atom H99A and the deepest hole is located 0.19 \%A from atom H971. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18747 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.44 _reflns_number_total 5008 _reflns_number_gt 4138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2008)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0419P)^2^+1.1056P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5008 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.06530(4) 0.18368(3) 0.69487(2) 0.02194(10) Uani 1 1 d . . . O1 O -0.1164(2) 0.45077(18) 0.66424(19) 0.0420(5) Uani 1 1 d . . . H1O H -0.0537 0.4104 0.7354 0.063 Uiso 1 1 d . . . O2 O 0.0254(2) 0.15623(15) 0.56381(13) 0.0227(3) Uani 1 1 d . . . O3 O 0.8348(2) -0.00890(15) 0.21460(13) 0.0227(3) Uani 1 1 d . . . O4 O 0.9686(3) -0.33378(18) 0.16611(16) 0.0391(5) Uani 1 1 d . . . O5 O 0.3369(2) 0.20903(16) 0.60579(14) 0.0259(4) Uani 1 1 d . . . H5O H 0.4052 0.2222 0.6437 0.039 Uiso 1 1 d . . . O6 O -0.2356(2) 0.1636(2) 0.80761(15) 0.0397(5) Uani 1 1 d . . . O7 O -0.3836(2) 0.2217(2) 0.67267(15) 0.0391(5) Uani 1 1 d . . . O8 O -0.4950(3) 0.1458(3) 0.84405(19) 0.0662(8) Uani 1 1 d . . . N1 N -0.0675(3) 0.3551(2) 0.62050(19) 0.0292(5) Uani 1 1 d . . . N2 N -0.1015(3) 0.2583(2) 0.40807(17) 0.0336(5) Uani 1 1 d . . . H2N H -0.1635 0.3233 0.3589 0.050 Uiso 1 1 d . . . N3 N 0.9176(3) -0.2177(2) 0.17358(17) 0.0262(4) Uani 1 1 d . . . N4 N 0.7403(2) 0.10317(19) 0.04766(15) 0.0236(4) Uani 1 1 d . . . H4N H 0.7360 0.0960 -0.0143 0.035 Uiso 1 1 d . . . N5 N -0.3735(3) 0.1783(2) 0.77442(17) 0.0295(5) Uani 1 1 d . . . C1 C -0.1280(3) 0.3705(2) 0.5338(2) 0.0308(6) Uani 1 1 d . . . C2 C -0.2539(4) 0.4851(3) 0.4751(3) 0.0529(9) Uani 1 1 d . . . H2A H -0.2838 0.5475 0.5134 0.079 Uiso 1 1 calc R . . H2B H -0.3587 0.4619 0.4759 0.079 Uiso 1 1 calc R . . H2C H -0.2020 0.5212 0.3973 0.079 Uiso 1 1 calc R . . C3 C -0.0638(3) 0.2544(2) 0.50169(19) 0.0264(5) Uani 1 1 d . . . C4 C -0.0461(3) 0.1491(3) 0.3691(2) 0.0365(6) Uani 1 1 d . . . H4A H -0.1061 0.1685 0.3052 0.044 Uiso 1 1 calc R . . H4B H -0.0822 0.0765 0.4302 0.044 Uiso 1 1 calc R . . C5 C 0.1485(3) 0.1110(3) 0.3324(2) 0.0312(6) Uani 1 1 d . . . H5A H 0.2077 0.0829 0.3984 0.037 Uiso 1 1 calc R . . H5B H 0.1742 0.0381 0.3061 0.037 Uiso 1 1 calc R . . C6 C 0.2233(3) 0.2150(3) 0.2400(2) 0.0296(5) Uani 1 1 d . . . H6A H 0.2017 0.2871 0.2667 0.036 Uiso 1 1 calc R . . H6B H 0.1631 0.2448 0.1741 0.036 Uiso 1 1 calc R . . C7 C 0.4172(3) 0.1711(3) 0.2041(2) 0.0297(5) Uani 1 1 d . . . H7A H 0.4787 0.1565 0.2660 0.036 Uiso 1 1 calc R . . H7B H 0.4406 0.0896 0.1917 0.036 Uiso 1 1 calc R . . C8 C 0.4895(3) 0.2643(2) 0.0982(2) 0.0282(5) Uani 1 1 d . . . H8A H 0.4587 0.3475 0.1087 0.034 Uiso 1 1 calc R . . H8B H 0.4338 0.2742 0.0352 0.034 Uiso 1 1 calc R . . C9 C 0.6856(3) 0.2248(2) 0.0667(2) 0.0261(5) Uani 1 1 d . . . H9A H 0.7233 0.2900 -0.0022 0.031 Uiso 1 1 calc R . . H9B H 0.7423 0.2190 0.1277 0.031 Uiso 1 1 calc R . . C10 C 0.8261(3) -0.1289(3) -0.0121(2) 0.0316(6) Uani 1 1 d . . . H10A H 0.8594 -0.2172 -0.0090 0.047 Uiso 1 1 calc R . . H10B H 0.8973 -0.0808 -0.0757 0.047 Uiso 1 1 calc R . . H10C H 0.7039 -0.0933 -0.0213 0.047 Uiso 1 1 calc R . . C11 C 0.4289(4) 0.1650(4) 0.5178(3) 0.0660(12) Uani 1 1 d . . . H11A H 0.4453 0.0733 0.5423 0.099 Uiso 1 1 calc R . . H11B H 0.5419 0.1855 0.4950 0.099 Uiso 1 1 calc R . . H11C H 0.3642 0.2051 0.4542 0.099 Uiso 1 1 calc R . . C12 C 0.8527(3) -0.1220(2) 0.09376(19) 0.0239(5) Uani 1 1 d . . . C13 C 0.8070(3) -0.0039(2) 0.12171(18) 0.0218(5) Uani 1 1 d . . . C99 C 0.0000 0.5000 0.0000 0.078(2) Uani 1 2 d S . . O99 O -0.1333(8) 0.5487(5) 0.0780(5) 0.0697(15) Uani 0.50 1 d P . . H99 H -0.0864 0.6023 0.1020 0.105 Uiso 0.05 1 d P . . O98 O -0.3123(5) 0.4018(4) 0.2412(3) 0.0376(14) Uani 0.489(6) 1 d P A 1 C98 C -0.4831(12) 0.4751(10) 0.2532(9) 0.064(3) Uani 0.489(6) 1 d P A 1 H98A H -0.5584 0.4209 0.3051 0.096 Uiso 0.489(6) 1 calc PR A 1 H98B H -0.5231 0.5147 0.1799 0.096 Uiso 0.489(6) 1 calc PR A 1 H98C H -0.4866 0.5406 0.2829 0.096 Uiso 0.489(6) 1 calc PR A 1 O97 O -0.2559(6) 0.4885(4) 0.2384(3) 0.0445(14) Uani 0.511(6) 1 d P A 2 C97 C -0.4169(11) 0.5160(8) 0.2164(8) 0.052(2) Uani 0.511(6) 1 d P A 2 H97A H -0.4981 0.5585 0.2671 0.078 Uiso 0.511(6) 1 calc PR A 2 H97B H -0.4472 0.4379 0.2273 0.078 Uiso 0.511(6) 1 calc PR A 2 H97C H -0.4231 0.5715 0.1386 0.078 Uiso 0.511(6) 1 calc PR A 2 H98 H -0.2008 0.4246 0.2012 0.050 Uiso 1 1 d . B 2 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 0.01903(15) 0.02623(16) 0.02097(15) -0.00956(11) -0.00290(10) -0.00389(11) O1 0.0296(10) 0.0324(10) 0.0644(14) -0.0250(10) -0.0055(9) 0.0022(8) O2 0.0178(8) 0.0292(9) 0.0180(8) -0.0040(7) -0.0057(6) -0.0038(7) O3 0.0235(8) 0.0299(9) 0.0181(8) -0.0097(7) -0.0039(6) -0.0080(7) O4 0.0446(11) 0.0350(10) 0.0412(11) -0.0250(9) 0.0015(9) -0.0047(9) O5 0.0178(8) 0.0352(9) 0.0293(9) -0.0160(8) -0.0030(7) -0.0064(7) O6 0.0281(10) 0.0704(14) 0.0252(9) -0.0120(9) -0.0031(8) -0.0234(10) O7 0.0329(10) 0.0659(13) 0.0241(9) -0.0113(9) -0.0044(8) -0.0237(10) O8 0.0289(11) 0.126(2) 0.0375(12) -0.0122(13) 0.0072(9) -0.0381(14) N1 0.0161(9) 0.0293(11) 0.0384(12) -0.0125(9) 0.0016(9) -0.0031(8) N2 0.0169(10) 0.0536(14) 0.0167(10) -0.0018(9) -0.0044(8) -0.0012(9) N3 0.0200(10) 0.0323(11) 0.0295(11) -0.0177(9) 0.0024(8) -0.0060(8) N4 0.0214(10) 0.0359(11) 0.0162(9) -0.0102(8) -0.0008(7) -0.0100(8) N5 0.0235(10) 0.0467(13) 0.0224(10) -0.0108(9) 0.0008(8) -0.0181(10) C1 0.0129(11) 0.0307(13) 0.0385(14) -0.0026(11) -0.0014(10) -0.0044(10) C2 0.0265(15) 0.0356(16) 0.080(2) 0.0034(16) -0.0231(15) -0.0013(12) C3 0.0126(10) 0.0375(14) 0.0209(11) -0.0016(10) -0.0003(9) -0.0070(10) C4 0.0236(13) 0.0665(19) 0.0202(12) -0.0137(12) -0.0057(10) -0.0112(13) C5 0.0246(12) 0.0530(16) 0.0176(11) -0.0145(11) -0.0013(9) -0.0094(11) C6 0.0257(12) 0.0453(15) 0.0212(12) -0.0177(11) -0.0011(9) -0.0068(11) C7 0.0254(12) 0.0424(15) 0.0218(12) -0.0136(11) -0.0014(10) -0.0066(11) C8 0.0274(13) 0.0339(13) 0.0251(12) -0.0119(11) -0.0046(10) -0.0065(10) C9 0.0265(12) 0.0315(13) 0.0215(11) -0.0070(10) -0.0037(9) -0.0109(10) C10 0.0322(13) 0.0471(16) 0.0260(13) -0.0210(12) 0.0011(10) -0.0167(12) C11 0.0276(15) 0.130(4) 0.073(2) -0.080(3) 0.0083(15) -0.0171(19) C12 0.0166(11) 0.0396(14) 0.0215(11) -0.0167(10) 0.0046(9) -0.0127(10) C13 0.0140(10) 0.0369(13) 0.0183(11) -0.0119(10) 0.0038(8) -0.0127(9) C99 0.105(5) 0.052(3) 0.041(3) -0.020(2) -0.010(3) 0.033(3) O99 0.088(4) 0.076(4) 0.064(3) -0.031(3) -0.012(3) -0.035(3) O98 0.032(2) 0.040(3) 0.037(2) -0.0148(18) -0.0163(17) 0.0075(17) C98 0.050(6) 0.077(7) 0.076(7) -0.045(6) -0.036(5) 0.017(4) O97 0.061(3) 0.037(2) 0.035(2) -0.0023(17) -0.0195(19) -0.013(2) C97 0.043(5) 0.053(5) 0.054(5) -0.003(4) -0.017(4) -0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.952(2) 2_656 ? Cu1 N1 1.972(2) . ? Cu1 O3 1.9749(17) 2_656 ? Cu1 O2 1.9770(16) . ? Cu1 O5 2.3009(16) . ? O1 N1 1.363(3) . ? O1 H1O 1.0503 . ? O2 C3 1.261(3) . ? O3 C13 1.264(3) . ? O3 Cu1 1.9749(17) 2_656 ? O4 N3 1.338(3) . ? O5 C11 1.391(3) . ? O5 H5O 0.9152 . ? O6 N5 1.254(3) . ? O7 N5 1.241(3) . ? O8 N5 1.222(3) . ? N1 C1 1.276(4) . ? N2 C3 1.314(3) . ? N2 C4 1.467(4) . ? N2 H2N 0.8968 . ? N3 C12 1.285(3) . ? N3 Cu1 1.952(2) 2_656 ? N4 C13 1.317(3) . ? N4 C9 1.463(3) . ? N4 H4N 0.8546 . ? C1 C3 1.488(4) . ? C1 C2 1.491(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C4 C5 1.526(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.521(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.521(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.529(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C12 1.487(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.488(3) . ? C99 O99 1.437(6) 2_565 ? C99 O99 1.437(6) . ? O99 H99 1.0069 . ? O98 C98 1.408(9) . ? O98 H98 0.9978 . ? C98 H98A 0.9800 . ? C98 H98B 0.9800 . ? C98 H98C 0.9800 . ? O97 C97 1.340(9) . ? O97 H98 0.9836 . ? C97 H97A 0.9800 . ? C97 H97B 0.9800 . ? C97 H97C 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 N3 Cu1 N1 95.64(9) 2_656 . ? N3 Cu1 O3 81.83(8) 2_656 2_656 ? N1 Cu1 O3 171.24(7) . 2_656 ? N3 Cu1 O2 174.82(7) 2_656 . ? N1 Cu1 O2 81.01(8) . . ? O3 Cu1 O2 100.90(6) 2_656 . ? N3 Cu1 O5 94.18(7) 2_656 . ? N1 Cu1 O5 97.98(7) . . ? O3 Cu1 O5 90.59(6) 2_656 . ? O2 Cu1 O5 90.21(6) . . ? N1 O1 H1O 102.2 . . ? C3 O2 Cu1 111.91(16) . . ? C13 O3 Cu1 111.47(15) . 2_656 ? C11 O5 Cu1 124.53(17) . . ? C11 O5 H5O 113.7 . . ? Cu1 O5 H5O 118.1 . . ? C1 N1 O1 119.0(2) . . ? C1 N1 Cu1 116.48(18) . . ? O1 N1 Cu1 123.91(17) . . ? C3 N2 C4 122.8(2) . . ? C3 N2 H2N 128.4 . . ? C4 N2 H2N 108.8 . . ? C12 N3 O4 121.2(2) . . ? C12 N3 Cu1 116.27(16) . 2_656 ? O4 N3 Cu1 122.54(16) . 2_656 ? C13 N4 C9 123.57(19) . . ? C13 N4 H4N 113.8 . . ? C9 N4 H4N 122.6 . . ? O8 N5 O7 121.1(2) . . ? O8 N5 O6 118.5(2) . . ? O7 N5 O6 120.3(2) . . ? N1 C1 C3 110.7(2) . . ? N1 C1 C2 125.7(3) . . ? C3 C1 C2 123.5(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O2 C3 N2 122.1(2) . . ? O2 C3 C1 119.6(2) . . ? N2 C3 C1 118.3(2) . . ? N2 C4 C5 114.0(2) . . ? N2 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N2 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.6(2) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 112.5(2) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 113.7(2) . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 113.8(2) . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? N4 C9 C8 111.84(19) . . ? N4 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? N4 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C12 C10 H10A 109.5 . . ? C12 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C12 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C10 124.3(2) . . ? N3 C12 C13 111.0(2) . . ? C10 C12 C13 124.7(2) . . ? O3 C13 N4 122.1(2) . . ? O3 C13 C12 119.4(2) . . ? N4 C13 C12 118.5(2) . . ? O99 C99 O99 180.0(5) 2_565 . ? C99 O99 H99 107.7 . . ? C98 O98 H98 132.4 . . ? C97 O97 H98 98.5 . . ? O97 C97 H97A 109.5 . . ? O97 C97 H97B 109.5 . . ? H97A C97 H97B 109.5 . . ? O97 C97 H97C 109.5 . . ? H97A C97 H97C 109.5 . . ? H97B C97 H97C 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 O1 H1O O4 1.05 1.46 2.500(3) 170.2 2_656 O1 H1O N3 1.05 2.20 3.034(3) 134.5 2_656 O5 H5O O7 0.92 1.87 2.721(2) 154.1 1_655 N4 H4N O6 0.85 2.13 2.903(3) 151.0 1_654 O99 H99 O4 1.01 1.54 2.527(5) 166.7 1_465 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.217 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.072 # start Validation Reply Form _vrf_PUBL772_GLOBAL ; PROBLEM: Suspect O-H Bond in CIF: O4---H1O .. 1.48 Ang. RESPONSE: The OH hydrogen atom H1O was alternatively bonded to O1 or O4. Therefore the apparent O1-H10 bond was unusually long and the non-bonding distance O4...H10 too short. ; # end Validation Reply Form # Attachment '- 4b.cif' data_4b _database_code_depnum_ccdc_archive 'CCDC 764191' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H50 Cl2 Cu2 N8 O18, 2(C H4 O)' _chemical_formula_sum 'C28 H58 Cl2 Cu2 N8 O20' _chemical_formula_weight 1024.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9391(6) _cell_length_b 11.1600(5) _cell_length_c 13.9690(10) _cell_angle_alpha 104.862(5) _cell_angle_beta 100.172(6) _cell_angle_gamma 104.269(5) _cell_volume 1120.71(13) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1004 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 1.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7391 _exptl_absorpt_correction_T_max 0.9137 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _publ_section_exptl_refinement ; The NH and OH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.15 \%A from atom H13A and the deepest hole is located 0.75 \%A from atom C7. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20908 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0683 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5134 _reflns_number_gt 3626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker, 2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0483P)^2^+2.5943P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5134 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 Cu1 Cu 0.73401(6) 0.23591(4) 0.86356(3) 0.01593(13) Uani 1 1 d . . . Cl1 Cl 0.31176(12) 0.18738(8) 0.67343(6) 0.0201(2) Uani 1 1 d . . . O5 O 1.0069(3) 0.2563(2) 0.9518(2) 0.0268(6) Uani 1 1 d . . . H1O H 1.0805 0.3323 1.0038 0.040 Uiso 1 1 d R . . O2 O 0.7089(3) 0.0648(2) 0.76823(17) 0.0180(5) Uani 1 1 d . . . O1 O 0.8275(4) 0.4151(2) 0.74475(19) 0.0234(6) Uani 1 1 d . . . H3O H 0.8226 0.4619 0.8045 0.035 Uiso 1 1 d R . . O3 O 1.3657(3) -0.1814(2) 1.03041(18) 0.0179(5) Uani 1 1 d . . . O4 O 1.2137(3) -0.5129(2) 1.08035(19) 0.0208(6) Uani 1 1 d . . . O6 O 0.3936(4) 0.2077(3) 0.77828(19) 0.0252(6) Uani 1 1 d . . . O7 O 0.3295(4) 0.0690(3) 0.6117(2) 0.0355(7) Uani 1 1 d . . . O8 O 0.4059(4) 0.2926(3) 0.6421(2) 0.0337(7) Uani 1 1 d . . . O9 O 0.1298(4) 0.1821(4) 0.6611(3) 0.0508(9) Uani 1 1 d . . . O10 O 0.4177(6) 0.5581(3) 0.6891(2) 0.0548(10) Uani 1 1 d . . . H10O H 0.4330 0.4861 0.6769 0.082 Uiso 1 1 d R . . N1 N 0.7881(4) 0.2906(3) 0.7466(2) 0.0173(6) Uani 1 1 d . . . N2 N 0.7157(4) -0.0317(3) 0.6064(2) 0.0183(6) Uani 1 1 d . . . H2N H 0.7281 -0.0200 0.5393 0.027 Uiso 1 1 d R . . N3 N 1.2631(4) -0.4060(3) 1.0529(2) 0.0155(6) Uani 1 1 d . . . N4 N 1.4077(4) -0.2643(3) 0.8755(2) 0.0162(6) Uani 1 1 d . . . H4N H 1.3818 -0.3341 0.8239 0.024 Uiso 1 1 d R . . C1 C 0.7677(5) 0.2004(3) 0.6637(3) 0.0164(7) Uani 1 1 d . . . C2 C 0.7783(5) 0.2208(4) 0.5646(3) 0.0236(8) Uani 1 1 d . . . H2A H 0.7729 0.3084 0.5674 0.035 Uiso 1 1 calc R . . H2B H 0.6773 0.1559 0.5103 0.035 Uiso 1 1 calc R . . H2C H 0.8917 0.2117 0.5502 0.035 Uiso 1 1 calc R . . C3 C 0.7286(4) 0.0712(3) 0.6820(3) 0.0151(7) Uani 1 1 d . . . C4 C 0.6791(5) -0.1629(3) 0.6144(3) 0.0225(8) Uani 1 1 d . . . H4A H 0.5881 -0.2249 0.5521 0.027 Uiso 1 1 calc R . . H4B H 0.6292 -0.1661 0.6741 0.027 Uiso 1 1 calc R . . C5 C 0.8497(6) -0.2038(4) 0.6263(3) 0.0399(11) Uani 1 1 d . . . H5A H 0.8162 -0.2968 0.6222 0.048 Uiso 1 1 calc R . . H5B H 0.9016 -0.1956 0.5680 0.048 Uiso 1 1 calc R . . C6 C 0.9890(6) -0.1285(4) 0.7222(4) 0.0359(10) Uani 1 1 d . . . H6A H 0.9320 -0.1290 0.7797 0.043 Uiso 1 1 calc R . . H6B H 1.0293 -0.0370 0.7224 0.043 Uiso 1 1 calc R . . C7 C 1.1513(6) -0.1704(4) 0.7439(4) 0.0359(10) Uani 1 1 d . . . H7A H 1.1122 -0.2604 0.7470 0.043 Uiso 1 1 calc R . . H7B H 1.2062 -0.1733 0.6854 0.043 Uiso 1 1 calc R . . C8 C 1.2919(6) -0.0898(4) 0.8386(3) 0.0358(10) Uani 1 1 d . . . H8C H 1.2371 -0.0855 0.8974 0.043 Uiso 1 1 calc R . . H8D H 1.3335 -0.0001 0.8352 0.043 Uiso 1 1 calc R . . C9 C 1.4551(5) -0.1367(3) 0.8598(3) 0.0195(8) Uani 1 1 d . . . H9C H 1.5105 -0.1421 0.8013 0.023 Uiso 1 1 calc R . . H9D H 1.5450 -0.0725 0.9215 0.023 Uiso 1 1 calc R . . C10 C 1.3167(5) -0.5282(3) 0.8937(3) 0.0206(8) Uani 1 1 d . . . H10A H 1.2147 -0.5554 0.8336 0.031 Uiso 1 1 calc R . . H10B H 1.3098 -0.5984 0.9243 0.031 Uiso 1 1 calc R . . H10C H 1.4293 -0.5089 0.8728 0.031 Uiso 1 1 calc R . . C11 C 1.0898(6) 0.1618(4) 0.9610(4) 0.0391(11) Uani 1 1 d . . . H11A H 1.0000 0.0754 0.9329 0.059 Uiso 1 1 calc R . . H11B H 1.1448 0.1778 1.0335 0.059 Uiso 1 1 calc R . . H11C H 1.1828 0.1658 0.9232 0.059 Uiso 1 1 calc R . . C12 C 1.3111(4) -0.4100(3) 0.9698(3) 0.0146(7) Uani 1 1 d . . . C13 C 1.3635(4) -0.2780(3) 0.9590(3) 0.0149(7) Uani 1 1 d . . . C14 C 0.2787(13) 0.5303(7) 0.6024(5) 0.108(3) Uani 1 1 d . . . H14A H 0.1760 0.4600 0.6019 0.161 Uiso 1 1 calc R . . H14B H 0.3203 0.5031 0.5407 0.161 Uiso 1 1 calc R . . H14C H 0.2421 0.6083 0.6037 0.161 Uiso 1 1 calc R . . 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 0.0217(2) 0.0129(2) 0.0133(2) 0.00300(16) 0.00667(17) 0.00521(17) Cl1 0.0222(5) 0.0227(4) 0.0172(4) 0.0053(3) 0.0055(4) 0.0109(4) O5 0.0221(14) 0.0144(12) 0.0343(16) -0.0007(11) -0.0044(12) 0.0058(11) O2 0.0235(13) 0.0175(12) 0.0120(12) 0.0018(10) 0.0054(10) 0.0069(11) O1 0.0331(15) 0.0168(12) 0.0225(14) 0.0077(11) 0.0129(12) 0.0061(12) O3 0.0249(14) 0.0125(11) 0.0154(12) 0.0023(10) 0.0072(11) 0.0052(10) O4 0.0292(14) 0.0112(11) 0.0212(13) 0.0061(10) 0.0076(11) 0.0031(11) O6 0.0301(15) 0.0307(14) 0.0133(13) 0.0034(11) 0.0034(11) 0.0120(12) O7 0.060(2) 0.0246(14) 0.0211(15) 0.0021(12) 0.0075(14) 0.0187(15) O8 0.0468(18) 0.0286(15) 0.0337(17) 0.0161(13) 0.0161(14) 0.0147(14) O9 0.0204(16) 0.081(3) 0.054(2) 0.025(2) 0.0050(15) 0.0206(17) O10 0.113(3) 0.0305(17) 0.0317(19) 0.0086(14) 0.033(2) 0.032(2) N1 0.0173(15) 0.0166(15) 0.0189(16) 0.0064(12) 0.0057(13) 0.0053(13) N2 0.0215(16) 0.0217(15) 0.0135(15) 0.0042(12) 0.0051(12) 0.0110(13) N3 0.0173(15) 0.0126(14) 0.0156(15) 0.0045(11) 0.0023(12) 0.0043(12) N4 0.0221(16) 0.0152(14) 0.0117(14) 0.0036(11) 0.0054(12) 0.0061(13) C1 0.0130(17) 0.0220(18) 0.0164(18) 0.0065(14) 0.0058(14) 0.0074(15) C2 0.026(2) 0.029(2) 0.0188(19) 0.0093(16) 0.0089(16) 0.0103(17) C3 0.0094(16) 0.0217(18) 0.0138(17) 0.0042(14) 0.0012(13) 0.0068(14) C4 0.025(2) 0.0173(18) 0.0206(19) 0.0006(15) 0.0014(16) 0.0068(16) C5 0.049(3) 0.036(2) 0.033(2) 0.005(2) 0.009(2) 0.017(2) C6 0.034(2) 0.031(2) 0.043(3) 0.019(2) -0.001(2) 0.010(2) C7 0.037(3) 0.023(2) 0.044(3) 0.0092(19) -0.002(2) 0.0119(19) C8 0.044(3) 0.032(2) 0.032(2) 0.0102(19) 0.009(2) 0.014(2) C9 0.026(2) 0.0145(17) 0.0209(19) 0.0089(14) 0.0084(16) 0.0060(15) C10 0.030(2) 0.0146(17) 0.0180(18) 0.0036(14) 0.0087(16) 0.0086(16) C11 0.038(3) 0.024(2) 0.047(3) 0.006(2) -0.006(2) 0.014(2) C12 0.0149(17) 0.0134(16) 0.0174(17) 0.0063(14) 0.0041(14) 0.0062(14) C13 0.0125(17) 0.0149(16) 0.0151(17) 0.0025(14) 0.0009(14) 0.0047(14) C14 0.210(10) 0.063(4) 0.049(4) 0.001(3) -0.003(5) 0.083(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 N3 1.949(3) 2_757 ? Cu1 O3 1.957(2) 2_757 ? Cu1 N1 1.963(3) . ? Cu1 O2 1.968(2) . ? Cu1 O5 2.222(3) . ? Cl1 O9 1.409(3) . ? Cl1 O6 1.428(3) . ? Cl1 O7 1.435(3) . ? Cl1 O8 1.440(3) . ? O5 C11 1.393(5) . ? O5 H1O 0.9373 . ? O2 C3 1.259(4) . ? O1 N1 1.356(4) . ? O1 H3O 0.8766 . ? O3 C13 1.261(4) . ? O3 Cu1 1.957(2) 2_757 ? O4 N3 1.334(4) . ? O10 C14 1.395(8) . ? O10 H10O 0.8217 . ? N1 C1 1.279(4) . ? N2 C3 1.314(4) . ? N2 C4 1.457(5) . ? N2 H2N 0.9986 . ? N3 C12 1.279(4) . ? N3 Cu1 1.949(3) 2_757 ? N4 C13 1.310(4) . ? N4 C9 1.464(4) . ? N4 H4N 0.8655 . ? C1 C2 1.472(5) . ? C1 C3 1.496(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C4 C5 1.527(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.471(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.484(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.476(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.522(5) . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 H9C 0.9900 . ? C9 H9D 0.9900 . ? C10 C12 1.483(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.483(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 N3 Cu1 O3 81.76(11) 2_757 2_757 ? N3 Cu1 N1 96.15(12) 2_757 . ? O3 Cu1 N1 169.22(11) 2_757 . ? N3 Cu1 O2 173.72(11) 2_757 . ? O3 Cu1 O2 100.04(10) 2_757 . ? N1 Cu1 O2 80.95(11) . . ? N3 Cu1 O5 92.85(11) 2_757 . ? O3 Cu1 O5 89.30(10) 2_757 . ? N1 Cu1 O5 101.39(11) . . ? O2 Cu1 O5 93.18(10) . . ? O9 Cl1 O6 110.02(19) . . ? O9 Cl1 O7 111.2(2) . . ? O6 Cl1 O7 108.76(16) . . ? O9 Cl1 O8 109.8(2) . . ? O6 Cl1 O8 109.23(17) . . ? O7 Cl1 O8 107.74(17) . . ? C11 O5 Cu1 130.3(2) . . ? C11 O5 H1O 104.7 . . ? Cu1 O5 H1O 123.6 . . ? C3 O2 Cu1 112.3(2) . . ? N1 O1 H3O 105.8 . . ? C13 O3 Cu1 111.5(2) . 2_757 ? C14 O10 H10O 97.9 . . ? C1 N1 O1 118.1(3) . . ? C1 N1 Cu1 117.0(2) . . ? O1 N1 Cu1 124.6(2) . . ? C3 N2 C4 123.6(3) . . ? C3 N2 H2N 118.2 . . ? C4 N2 H2N 118.1 . . ? C12 N3 O4 121.5(3) . . ? C12 N3 Cu1 116.3(2) . 2_757 ? O4 N3 Cu1 122.3(2) . 2_757 ? C13 N4 C9 121.3(3) . . ? C13 N4 H4N 117.4 . . ? C9 N4 H4N 119.5 . . ? N1 C1 C2 125.0(3) . . ? N1 C1 C3 109.9(3) . . ? C2 C1 C3 125.1(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O2 C3 N2 122.5(3) . . ? O2 C3 C1 119.4(3) . . ? N2 C3 C1 118.1(3) . . ? N2 C4 C5 111.2(3) . . ? N2 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 115.0(4) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C5 C6 C7 118.2(4) . . ? C5 C6 H6A 107.8 . . ? C7 C6 H6A 107.8 . . ? C5 C6 H6B 107.8 . . ? C7 C6 H6B 107.8 . . ? H6A C6 H6B 107.1 . . ? C8 C7 C6 116.9(4) . . ? C8 C7 H7A 108.1 . . ? C6 C7 H7A 108.1 . . ? C8 C7 H7B 108.1 . . ? C6 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C7 C8 C9 115.6(4) . . ? C7 C8 H8C 108.4 . . ? C9 C8 H8C 108.4 . . ? C7 C8 H8D 108.4 . . ? C9 C8 H8D 108.4 . . ? H8C C8 H8D 107.4 . . ? N4 C9 C8 112.0(3) . . ? N4 C9 H9C 109.2 . . ? C8 C9 H9C 109.2 . . ? N4 C9 H9D 109.2 . . ? C8 C9 H9D 109.2 . . ? H9C C9 H9D 107.9 . . ? C12 C10 H10A 109.5 . . ? C12 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C12 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C10 125.9(3) . . ? N3 C12 C13 110.6(3) . . ? C10 C12 C13 123.5(3) . . ? O3 C13 N4 121.4(3) . . ? O3 C13 C12 119.4(3) . . ? N4 C13 C12 119.2(3) . . ? O10 C14 H14A 109.5 . . ? O10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 O10 H10O O8 0.82 2.04 2.840(4) 166.2 . N2 H2N O7 1.00 1.97 2.911(4) 155.2 2_656 N2 H2N Cl1 1.00 2.99 3.792(3) 137.9 2_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.715 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.103 # Attachment '- 5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 764192' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H54 Cu2 N8 O10, C26 H48.68 Cu2 N8 O9.34, 1.66(C H4 O), 4(N O3)' _chemical_formula_sum 'C55.67 H109.33 Cu4 N20 O33' _chemical_formula_weight 1841.12 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 monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.6862(17) _cell_length_b 37.800(8) _cell_length_c 13.270(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.79(3) _cell_angle_gamma 90.00 _cell_volume 4326.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2051 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1927 _exptl_absorpt_coefficient_mu 1.058 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8226 _exptl_absorpt_correction_T_max 0.9451 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The crystal was poorly diffracting plate. Due to the poor diffraction power the data completeness was low. The N---O and O...O distances in one of the NO~3~^-^ counter anion were constrained to be equal. The coordinated water molecule (O5B) was disordered with a MeOH solvent molecule (O16, C16). These molecules were refined with occupancies 0.6666 and 0.3333 respectively. The second MeOH solvent molecule was refined with occupancy 0.5. The non-hydrogen atoms in the constrained NO~3~^-^ and the disordered MeOH were restrained so that their U~ij~ components approximate to isotropic behavior. The OH and H~2~O hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, N---H = 0.88 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.62 \%A from atom H5P and the deepest hole is located 0.83 \%A from atom O6. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9540 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.25 _reflns_number_total 5332 _reflns_number_gt 3646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2008)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1176P)^2^+19.6208P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5332 _refine_ls_number_parameters 545 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.1187 _refine_ls_R_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.2430 _refine_ls_wR_factor_gt 0.2163 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.098 _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 Cu1 Cu 0.31152(13) 0.41874(3) 0.28360(9) 0.0421(4) Uani 1 1 d . . . Cu2 Cu 0.19843(13) 0.40492(3) 0.68115(9) 0.0447(4) Uani 1 1 d . . . O1 O 0.0990(7) 0.47832(15) 0.2472(5) 0.0502(17) Uani 1 1 d . . . O2 O 0.2621(7) 0.47862(15) 0.4127(5) 0.0445(16) Uani 1 1 d . . . H2O H 0.1953 0.4804 0.3283 0.067 Uiso 1 1 d R . . O3 O 0.2529(7) 0.38681(15) 0.1675(5) 0.0465(16) Uani 1 1 d . . . O4 O 0.4466(7) 0.38667(15) 0.3709(5) 0.0418(15) Uani 1 1 d . . . O5 O 0.4985(8) 0.44364(16) 0.2120(5) 0.0609(19) Uani 1 1 d . . . H5O H 0.5858 0.4310 0.1956 0.091 Uiso 1 1 d R . . N1 N 0.1432(9) 0.44663(18) 0.2113(6) 0.045(2) Uani 1 1 d . . . N2 N 0.3334(9) 0.44699(18) 0.4060(6) 0.0395(18) Uani 1 1 d . . . N3 N 0.1019(10) 0.38382(18) 0.0194(6) 0.055(2) Uani 1 1 d . . . H3 H 0.0307 0.3940 -0.0236 0.066 Uiso 1 1 calc R . . N4 N 0.5824(8) 0.38382(19) 0.5256(6) 0.0420(19) Uani 1 1 d . . . H4 H 0.6079 0.3939 0.5850 0.050 Uiso 1 1 calc R . . C1 C 0.0788(11) 0.4348(2) 0.1253(7) 0.045(2) Uani 1 1 d . . . C2 C -0.0429(12) 0.4536(2) 0.0576(8) 0.057(3) Uani 1 1 d . . . H2A H -0.0740 0.4750 0.0915 0.086 Uiso 1 1 calc R . . H2B H -0.1330 0.4380 0.0423 0.086 Uiso 1 1 calc R . . H2C H -0.0021 0.4600 -0.0056 0.086 Uiso 1 1 calc R . . C3 C 0.1496(13) 0.3998(2) 0.1054(8) 0.049(3) Uani 1 1 d . . . C4 C 0.1648(13) 0.3493(2) -0.0068(8) 0.057(3) Uani 1 1 d . . . H4A H 0.2761 0.3484 0.0198 0.068 Uiso 1 1 calc R . . H4B H 0.1572 0.3474 -0.0816 0.068 Uiso 1 1 calc R . . C5 C 0.0851(11) 0.3181(2) 0.0333(8) 0.049(3) Uani 1 1 d . . . H5A H -0.0272 0.3193 0.0095 0.059 Uiso 1 1 calc R . . H5B H 0.0980 0.3189 0.1084 0.059 Uiso 1 1 calc R . . C6 C 0.1506(12) 0.2836(2) -0.0017(8) 0.051(3) Uani 1 1 d . . . H6A H 0.2637 0.2833 0.0196 0.061 Uiso 1 1 calc R . . H6B H 0.1350 0.2830 -0.0768 0.061 Uiso 1 1 calc R . . C7 C 0.0803(16) 0.2500 0.0383(10) 0.046(3) Uani 1 2 d S . . H7A H 0.0978 0.2500 0.1134 0.055 Uiso 1 2 calc SR . . H7B H -0.0331 0.2500 0.0177 0.055 Uiso 1 2 calc SR . . C8 C 0.4262(10) 0.4356(2) 0.4821(7) 0.039(2) Uani 1 1 d . . . C9 C 0.4641(11) 0.4550(2) 0.5786(7) 0.046(2) Uani 1 1 d . . . H9A H 0.5533 0.4705 0.5735 0.069 Uiso 1 1 calc R . . H9B H 0.4894 0.4380 0.6340 0.069 Uiso 1 1 calc R . . H9C H 0.3747 0.4693 0.5923 0.069 Uiso 1 1 calc R . . C10 C 0.4863(10) 0.4005(2) 0.4568(7) 0.039(2) Uani 1 1 d . . . C11 C 0.6474(11) 0.3494(2) 0.5063(8) 0.050(3) Uani 1 1 d . . . H11A H 0.7521 0.3479 0.5447 0.061 Uiso 1 1 calc R . . H11B H 0.6600 0.3479 0.4332 0.061 Uiso 1 1 calc R . . C12 C 0.5545(11) 0.3181(2) 0.5336(7) 0.046(2) Uani 1 1 d . . . H12A H 0.4525 0.3183 0.4915 0.055 Uiso 1 1 calc R . . H12B H 0.5359 0.3201 0.6055 0.055 Uiso 1 1 calc R . . C13 C 0.6347(11) 0.2834(2) 0.5181(8) 0.051(3) Uani 1 1 d . . . H13A H 0.7339 0.2831 0.5633 0.062 Uiso 1 1 calc R . . H13B H 0.6603 0.2828 0.4473 0.062 Uiso 1 1 calc R . . C14 C 0.5464(16) 0.2500 0.5370(11) 0.051(4) Uani 1 2 d S . . H14A H 0.4467 0.2500 0.4923 0.061 Uiso 1 2 calc SR . . H14B H 0.5227 0.2500 0.6081 0.061 Uiso 1 2 calc SR . . O1B O 0.1584(8) 0.46456(17) 0.8150(5) 0.0515(17) Uani 1 1 d . . . O2B O -0.0041(7) 0.46623(16) 0.6515(5) 0.0496(17) Uani 1 1 d . . . H2P H 0.0710 0.4721 0.7233 0.074 Uiso 1 1 d R A . O3B O 0.3838(8) 0.38046(18) 0.7466(5) 0.0578(19) Uani 1 1 d . A . O4B O 0.1735(7) 0.38087(15) 0.5479(5) 0.0435(15) Uani 1 1 d . A . O5B O 0.0426(11) 0.3666(3) 0.7456(7) 0.064(3) Uani 0.67 1 d PU A 1 H5P H -0.0330 0.3800 0.7573 0.096 Uiso 0.67 1 d PR A 1 H5Z H 0.0072 0.3466 0.7254 0.096 Uiso 0.67 1 d PR A 1 O16 O 0.021(2) 0.3224(6) 0.6921(15) 0.068(6) Uani 0.33 1 d PU B 2 H16O H -0.0528 0.3066 0.7212 0.102 Uiso 0.33 1 d PR B 2 C16 C 0.163(3) 0.3005(8) 0.675(2) 0.057(8) Uani 0.33 1 d PU B 2 H16A H 0.1859 0.3034 0.6052 0.085 Uiso 0.33 1 calc PR B 2 H16B H 0.1433 0.2755 0.6882 0.085 Uiso 0.33 1 calc PR B 2 H16C H 0.2525 0.3085 0.7220 0.085 Uiso 0.33 1 calc PR B 2 N1B N 0.2421(9) 0.4357(2) 0.8005(6) 0.0426(19) Uani 1 1 d . A . N2B N 0.0480(8) 0.43710(19) 0.6088(6) 0.0398(18) Uani 1 1 d . A . N3B N 0.5418(10) 0.3794(2) 0.8939(7) 0.062(2) Uani 1 1 d . . . H3N H 0.5689 0.3892 0.9535 0.075 Uiso 1 1 calc R . . N4B N 0.0291(8) 0.38230(18) 0.3973(6) 0.0429(19) Uani 1 1 d . . . H4N H -0.0409 0.3936 0.3560 0.052 Uiso 1 1 calc R . . C1B C 0.3543(12) 0.4264(3) 0.8659(8) 0.049(3) Uani 1 1 d . . . C2B C 0.4112(12) 0.4455(3) 0.9611(8) 0.058(3) Uani 1 1 d . A . H2B1 H 0.3457 0.4662 0.9683 0.087 Uiso 1 1 calc R . . H2B2 H 0.5184 0.4531 0.9583 0.087 Uiso 1 1 calc R . . H2B3 H 0.4070 0.4297 1.0192 0.087 Uiso 1 1 calc R . . C3B C 0.4285(12) 0.3936(3) 0.8321(8) 0.054(3) Uani 1 1 d . A . C4B C 0.6242(14) 0.3475(3) 0.8657(10) 0.076(4) Uani 1 1 d . . . H4B1 H 0.7314 0.3476 0.9005 0.091 Uiso 1 1 calc R . . H4B2 H 0.6293 0.3473 0.7915 0.091 Uiso 1 1 calc R . . C5B C 0.5406(17) 0.3157(3) 0.8955(11) 0.097(4) Uani 1 1 d . . . H5B1 H 0.4330 0.3157 0.8612 0.117 Uiso 1 1 calc R . . H5B2 H 0.5368 0.3156 0.9697 0.117 Uiso 1 1 calc R . . C6B C 0.6317(18) 0.2820(3) 0.8625(14) 0.118(6) Uani 1 1 d . . . H6B1 H 0.6387 0.2828 0.7886 0.141 Uiso 1 1 calc R . . H6B2 H 0.7383 0.2819 0.8984 0.141 Uiso 1 1 calc R . . C7B C 0.550(3) 0.2500 0.888(2) 0.143(10) Uani 1 2 d S . . H7B1 H 0.4448 0.2500 0.8498 0.172 Uiso 1 2 calc SR . . H7B2 H 0.5393 0.2500 0.9609 0.172 Uiso 1 2 calc SR . . C8B C -0.0041(10) 0.4287(2) 0.5168(7) 0.036(2) Uani 1 1 d . . . C9B C -0.1224(10) 0.4493(2) 0.4515(7) 0.044(2) Uani 1 1 d . A . H9B1 H -0.1738 0.4659 0.4936 0.067 Uiso 1 1 calc R . . H9B2 H -0.1994 0.4332 0.4168 0.067 Uiso 1 1 calc R . . H9B3 H -0.0719 0.4626 0.4011 0.067 Uiso 1 1 calc R . . C10B C 0.0706(10) 0.3959(2) 0.4884(8) 0.039(2) Uani 1 1 d . A . C11B C 0.0936(10) 0.3493(2) 0.3613(7) 0.044(2) Uani 1 1 d . . . H11C H 0.2048 0.3478 0.3878 0.053 Uiso 1 1 calc R . . H11D H 0.0856 0.3497 0.2863 0.053 Uiso 1 1 calc R . . C12B C 0.0115(11) 0.3173(2) 0.3942(8) 0.048(2) Uani 1 1 d . . . H12C H -0.0992 0.3183 0.3661 0.057 Uiso 1 1 calc R . . H12D H 0.0171 0.3169 0.4692 0.057 Uiso 1 1 calc R . . C13B C 0.0838(11) 0.2836(2) 0.3582(8) 0.050(3) Uani 1 1 d . . . H13C H 0.0770 0.2842 0.2832 0.060 Uiso 1 1 calc R . . H13D H 0.1951 0.2832 0.3851 0.060 Uiso 1 1 calc R . . C14B C 0.0080(16) 0.2500 0.3903(12) 0.052(4) Uani 1 2 d S . . H14C H 0.0109 0.2500 0.4651 0.062 Uiso 1 2 calc SR . . H14D H -0.1022 0.2500 0.3610 0.062 Uiso 1 2 calc SR . . N6 N -0.2155(18) 0.4159(4) 0.7859(10) 0.170(7) Uani 1 1 d DU . . O6 O -0.3028(16) 0.4431(4) 0.8014(10) 0.180(6) Uani 1 1 d DU . . O7 O -0.1155(9) 0.4074(2) 0.8532(7) 0.091(3) Uani 1 1 d DU . . O8 O -0.2306(10) 0.4002(2) 0.7034(6) 0.084(3) Uani 1 1 d DU . . C15 C 0.5576(13) 0.4780(2) 0.2271(9) 0.068(3) Uani 1 1 d . . . H15A H 0.4741 0.4952 0.2102 0.102 Uiso 1 1 calc R . . H15B H 0.6393 0.4819 0.1833 0.102 Uiso 1 1 calc R . . H15C H 0.6006 0.4810 0.2982 0.102 Uiso 1 1 calc R . . N6B N 0.7550(11) 0.1172(3) 0.1708(8) 0.077(3) Uani 1 1 d . . . O6B O 0.7845(8) 0.0969(2) 0.2404(6) 0.064(2) Uani 1 1 d . . . O7B O 0.8284(14) 0.1434(5) 0.1685(12) 0.240(11) Uani 1 1 d . . . O8B O 0.6475(10) 0.1103(3) 0.1042(6) 0.119(4) Uani 1 1 d . . . C17 C 0.486(2) 0.1936(5) 0.2231(15) 0.053(5) Uani 0.50 1 d PU . . H17A H 0.4934 0.1990 0.2957 0.080 Uiso 0.50 1 calc PR . . H17B H 0.5113 0.1685 0.2142 0.080 Uiso 0.50 1 calc PR . . H17C H 0.3809 0.1983 0.1911 0.080 Uiso 0.50 1 calc PR . . O9 O 0.578(2) 0.2118(5) 0.1839(15) 0.112(6) Uani 0.50 1 d PU . . H9O H 0.6464 0.1963 0.1506 0.168 Uiso 0.50 1 d PR . . 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 0.0562(8) 0.0342(6) 0.0325(8) -0.0003(5) -0.0091(6) -0.0041(5) Cu2 0.0532(8) 0.0467(7) 0.0312(8) 0.0022(5) -0.0074(5) -0.0040(6) O1 0.061(4) 0.039(3) 0.047(5) -0.005(3) -0.011(3) -0.001(3) O2 0.057(4) 0.037(3) 0.036(4) -0.001(3) -0.005(3) -0.001(3) O3 0.064(4) 0.039(3) 0.032(4) 0.004(3) -0.014(3) 0.001(3) O4 0.051(4) 0.037(3) 0.036(4) -0.002(3) -0.004(3) -0.003(3) O5 0.089(5) 0.039(4) 0.057(5) -0.002(3) 0.020(4) -0.010(4) N1 0.064(5) 0.031(4) 0.038(5) 0.000(3) -0.008(4) -0.007(4) N2 0.052(5) 0.037(4) 0.028(5) 0.004(3) -0.005(4) -0.009(4) N3 0.094(7) 0.029(4) 0.035(5) 0.003(3) -0.016(5) -0.005(4) N4 0.046(5) 0.043(4) 0.034(5) -0.001(3) -0.006(4) -0.001(4) C1 0.060(6) 0.040(5) 0.030(6) 0.005(4) -0.010(5) -0.011(5) C2 0.065(7) 0.044(5) 0.054(7) 0.004(5) -0.026(5) -0.003(5) C3 0.072(7) 0.035(5) 0.039(7) 0.007(4) -0.001(6) -0.012(5) C4 0.090(8) 0.041(5) 0.035(7) 0.000(4) -0.011(6) -0.003(5) C5 0.063(6) 0.035(5) 0.047(7) 0.002(4) -0.009(5) -0.004(5) C6 0.069(7) 0.029(5) 0.053(7) -0.005(4) 0.002(5) 0.001(5) C7 0.065(9) 0.031(6) 0.040(9) 0.000 0.002(7) 0.000 C8 0.050(6) 0.033(5) 0.031(6) 0.001(4) -0.001(5) -0.008(4) C9 0.055(6) 0.048(5) 0.033(6) 0.001(4) -0.004(5) -0.003(5) C10 0.041(5) 0.041(5) 0.035(6) 0.004(4) -0.001(5) -0.015(4) C11 0.048(6) 0.050(6) 0.052(7) 0.002(5) -0.004(5) 0.003(5) C12 0.054(6) 0.044(5) 0.037(6) 0.004(4) -0.005(5) -0.005(5) C13 0.044(6) 0.041(5) 0.068(8) -0.001(5) 0.002(5) 0.000(4) C14 0.053(9) 0.060(9) 0.038(9) 0.000 -0.003(7) 0.000 O1B 0.064(4) 0.052(4) 0.037(4) -0.009(3) -0.001(3) -0.002(3) O2B 0.056(4) 0.050(4) 0.040(4) -0.009(3) -0.006(3) 0.007(3) O3B 0.064(5) 0.062(4) 0.041(5) 0.000(4) -0.018(4) 0.006(4) O4B 0.050(4) 0.046(3) 0.031(4) 0.003(3) -0.010(3) 0.006(3) O5B 0.071(6) 0.080(6) 0.037(6) 0.032(5) -0.011(5) -0.049(5) O16 0.070(9) 0.089(10) 0.047(9) 0.025(8) 0.013(8) 0.022(8) C16 0.074(12) 0.049(11) 0.043(11) 0.003(9) -0.014(9) 0.008(9) N1B 0.049(5) 0.050(5) 0.027(5) 0.001(4) -0.007(4) -0.015(4) N2B 0.042(4) 0.043(4) 0.033(5) -0.001(4) -0.003(4) -0.001(4) N3B 0.066(6) 0.073(6) 0.042(6) 0.012(5) -0.015(5) -0.006(5) N4B 0.048(5) 0.038(4) 0.042(5) 0.001(4) 0.001(4) 0.006(4) C1B 0.056(6) 0.055(6) 0.035(7) 0.007(5) -0.003(5) -0.014(5) C2B 0.062(7) 0.071(7) 0.037(7) -0.003(5) -0.007(5) -0.009(6) C3B 0.052(6) 0.068(7) 0.037(7) 0.016(5) -0.015(5) -0.014(6) C4B 0.080(8) 0.070(8) 0.071(9) 0.018(7) -0.020(7) -0.003(7) C5B 0.109(11) 0.077(9) 0.100(12) -0.002(8) -0.018(9) -0.018(8) C6B 0.123(13) 0.060(9) 0.165(17) 0.016(9) -0.005(11) 0.002(9) C7B 0.20(3) 0.062(14) 0.17(3) 0.000 0.02(2) 0.000 C8B 0.039(5) 0.036(5) 0.031(6) 0.005(4) -0.006(4) -0.011(4) C9B 0.049(6) 0.047(5) 0.034(6) 0.003(4) -0.007(5) 0.003(5) C10B 0.042(5) 0.035(5) 0.039(7) 0.001(4) 0.001(5) -0.007(4) C11B 0.044(5) 0.038(5) 0.047(7) -0.008(4) -0.005(5) 0.005(4) C12B 0.045(6) 0.037(5) 0.059(7) -0.006(5) -0.001(5) -0.008(4) C13B 0.048(6) 0.042(5) 0.060(7) -0.009(5) 0.008(5) -0.005(5) C14B 0.052(9) 0.042(8) 0.061(11) 0.000 0.006(8) 0.000 N6 0.174(11) 0.162(10) 0.175(11) 0.019(9) 0.028(9) -0.028(9) O6 0.173(9) 0.197(10) 0.173(9) 0.023(8) 0.032(7) 0.005(8) O7 0.066(5) 0.105(6) 0.093(6) 0.040(5) -0.034(4) -0.015(4) O8 0.092(5) 0.098(6) 0.059(5) -0.004(4) -0.004(4) -0.024(5) C15 0.080(8) 0.040(6) 0.084(9) -0.013(6) 0.013(7) -0.019(5) N6B 0.042(6) 0.121(10) 0.065(8) 0.023(7) -0.008(5) -0.016(6) O6B 0.059(5) 0.072(5) 0.054(6) 0.001(4) -0.017(4) -0.002(4) O7B 0.125(10) 0.305(19) 0.261(18) 0.224(16) -0.105(11) -0.127(12) O8B 0.068(6) 0.246(13) 0.034(5) -0.008(7) -0.027(4) 0.012(7) C17 0.058(9) 0.058(9) 0.041(9) 0.004(7) -0.007(7) -0.016(8) O9 0.116(10) 0.099(9) 0.127(10) 0.005(8) 0.038(8) -0.006(8) _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 N2 1.934(7) . yes Cu1 N1 1.959(8) . yes Cu1 O4 1.966(6) . yes Cu1 O3 1.975(6) . yes Cu1 O5 2.189(7) . yes Cu2 N2B 1.953(7) . yes Cu2 N1B 1.967(8) . yes Cu2 O3B 1.967(7) . yes Cu2 O4B 1.977(6) . yes Cu2 O5B 2.221(8) . yes O1 N1 1.361(9) . ? O1 H2O 1.2849 . ? O2 N2 1.354(9) . ? O2 H2O 1.2009 . ? O3 C3 1.245(11) . ? O4 C10 1.263(10) . ? O5 C15 1.403(11) . ? O5 H5O 0.9439 . ? N1 C1 1.290(11) . ? N2 C8 1.289(11) . ? N3 C3 1.314(12) . ? N3 C4 1.472(12) . ? N3 H3 0.8800 . ? N4 C10 1.322(11) . ? N4 C11 1.452(11) . ? N4 H4 0.8800 . ? C1 C2 1.484(12) . ? C1 C3 1.496(13) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C4 C5 1.496(12) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.518(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.531(11) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C6 1.531(11) 4_565 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.478(12) . ? C8 C10 1.481(12) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 C12 1.502(12) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.510(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.514(11) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C13 1.514(11) 4_565 ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O1B N1B 1.337(9) . ? O1B H2P 1.3860 . ? O2B N2B 1.341(9) . ? O2B H2P 1.1118 . ? O3B C3B 1.258(11) . ? O4B C10B 1.257(10) . ? O5B H5P 0.8577 . ? O5B H5Z 0.8460 . ? O16 C16 1.53(3) . ? O16 H5Z 1.0303 . ? O16 H16O 0.9867 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1B C1B 1.276(12) . ? N2B C8B 1.291(10) . ? N3B C3B 1.318(12) . ? N3B C4B 1.470(14) . ? N3B H3N 0.8800 . ? N4B C10B 1.325(11) . ? N4B C11B 1.470(10) . ? N4B H4N 0.8800 . ? C1B C2B 1.488(13) . ? C1B C3B 1.491(15) . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C4B C5B 1.482(16) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.589(19) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.46(2) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C6B 1.46(2) 4_565 ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B C10B 1.467(12) . ? C8B C9B 1.485(12) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C11B C12B 1.496(12) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.519(12) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.516(11) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C13B 1.516(11) 4_565 ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? N6 O7 1.214(12) . ? N6 O8 1.239(12) . ? N6 O6 1.308(12) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N6B O7B 1.180(14) . ? N6B O6B 1.203(11) . ? N6B O8B 1.235(11) . ? C17 O9 1.21(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O9 H9O 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 N2 Cu1 N1 96.2(3) . . ? N2 Cu1 O4 81.6(3) . . ? N1 Cu1 O4 168.2(3) . . ? N2 Cu1 O3 169.3(3) . . ? N1 Cu1 O3 80.7(3) . . ? O4 Cu1 O3 99.4(3) . . ? N2 Cu1 O5 97.1(3) . . ? N1 Cu1 O5 96.0(3) . . ? O4 Cu1 O5 95.7(3) . . ? O3 Cu1 O5 93.5(3) . . ? N2B Cu2 N1B 94.7(3) . . ? N2B Cu2 O3B 167.2(3) . . ? N1B Cu2 O3B 81.6(3) . . ? N2B Cu2 O4B 81.4(3) . . ? N1B Cu2 O4B 169.4(3) . . ? O3B Cu2 O4B 100.1(3) . . ? N2B Cu2 O5B 101.1(3) . . ? N1B Cu2 O5B 98.3(4) . . ? O3B Cu2 O5B 91.6(3) . . ? O4B Cu2 O5B 92.1(3) . . ? N1 O1 H2O 99.5 . . ? N2 O2 H2O 99.4 . . ? C3 O3 Cu1 112.0(6) . . ? C10 O4 Cu1 110.9(6) . . ? C15 O5 Cu1 127.9(6) . . ? C15 O5 H5O 102.3 . . ? Cu1 O5 H5O 122.6 . . ? C1 N1 O1 120.3(8) . . ? C1 N1 Cu1 117.8(6) . . ? O1 N1 Cu1 121.8(6) . . ? C8 N2 O2 119.5(7) . . ? C8 N2 Cu1 117.6(6) . . ? O2 N2 Cu1 122.8(5) . . ? C3 N3 C4 121.6(9) . . ? C3 N3 H3 119.2 . . ? C4 N3 H3 119.2 . . ? C10 N4 C11 122.1(8) . . ? C10 N4 H4 119.0 . . ? C11 N4 H4 119.0 . . ? N1 C1 C2 124.9(9) . . ? N1 C1 C3 108.6(8) . . ? C2 C1 C3 126.5(9) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O3 C3 N3 121.5(9) . . ? O3 C3 C1 120.7(9) . . ? N3 C3 C1 117.7(9) . . ? N3 C4 C5 114.5(9) . . ? N3 C4 H4A 108.6 . . ? C5 C4 H4A 108.6 . . ? N3 C4 H4B 108.6 . . ? C5 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 111.3(8) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 115.3(8) . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C6 112.1(11) 4_565 . ? C6 C7 H7A 109.2 4_565 . ? C6 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 4_565 . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N2 C8 C9 124.6(8) . . ? N2 C8 C10 109.0(8) . . ? C9 C8 C10 126.3(9) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 N4 120.7(9) . . ? O4 C10 C8 120.6(8) . . ? N4 C10 C8 118.7(9) . . ? N4 C11 C12 115.6(8) . . ? N4 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? N4 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.4 . . ? C11 C12 C13 112.4(8) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 116.8(8) . . ? C12 C13 H13A 108.1 . . ? C14 C13 H13A 108.1 . . ? C12 C13 H13B 108.1 . . ? C14 C13 H13B 108.1 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C13 113.1(11) . 4_565 ? C13 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 4_565 . ? C13 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 4_565 . ? H14A C14 H14B 107.8 . . ? N1B O1B H2P 107.0 . . ? N2B O2B H2P 109.5 . . ? C3B O3B Cu2 111.2(7) . . ? C10B O4B Cu2 110.3(6) . . ? Cu2 O5B H5P 101.5 . . ? Cu2 O5B H5Z 132.5 . . ? H5P O5B H5Z 109.0 . . ? C16 O16 H5Z 133.0 . . ? C16 O16 H16O 107.7 . . ? H5Z O16 H16O 104.8 . . ? O16 C16 H16A 109.5 . . ? O16 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O16 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1B N1B O1B 120.8(8) . . ? C1B N1B Cu2 116.3(7) . . ? O1B N1B Cu2 122.9(6) . . ? C8B N2B O2B 120.3(7) . . ? C8B N2B Cu2 116.8(6) . . ? O2B N2B Cu2 122.9(6) . . ? C3B N3B C4B 121.7(10) . . ? C3B N3B H3N 119.2 . . ? C4B N3B H3N 119.2 . . ? C10B N4B C11B 123.6(8) . . ? C10B N4B H4N 118.2 . . ? C11B N4B H4N 118.2 . . ? N1B C1B C2B 126.4(10) . . ? N1B C1B C3B 110.4(9) . . ? C2B C1B C3B 123.2(9) . . ? C1B C2B H2B1 109.5 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C1B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? O3B C3B N3B 121.9(11) . . ? O3B C3B C1B 120.1(9) . . ? N3B C3B C1B 118.0(11) . . ? N3B C4B C5B 109.1(11) . . ? N3B C4B H4B1 109.9 . . ? C5B C4B H4B1 109.9 . . ? N3B C4B H4B2 109.9 . . ? C5B C4B H4B2 109.9 . . ? H4B1 C4B H4B2 108.3 . . ? C4B C5B C6B 107.5(12) . . ? C4B C5B H5B1 110.2 . . ? C6B C5B H5B1 110.2 . . ? C4B C5B H5B2 110.2 . . ? C6B C5B H5B2 110.2 . . ? H5B1 C5B H5B2 108.5 . . ? C7B C6B C5B 109.4(15) . . ? C7B C6B H6B1 109.8 . . ? C5B C6B H6B1 109.8 . . ? C7B C6B H6B2 109.8 . . ? C5B C6B H6B2 109.8 . . ? H6B1 C6B H6B2 108.3 . . ? C6B C7B C6B 112(2) . 4_565 ? C6B C7B H7B1 109.2 . . ? C6B C7B H7B1 109.2 4_565 . ? C6B C7B H7B2 109.2 . . ? C6B C7B H7B2 109.2 4_565 . ? H7B1 C7B H7B2 107.9 . . ? N2B C8B C10B 109.5(8) . . ? N2B C8B C9B 124.3(8) . . ? C10B C8B C9B 126.2(9) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? O4B C10B N4B 119.5(8) . . ? O4B C10B C8B 121.7(9) . . ? N4B C10B C8B 118.8(8) . . ? N4B C11B C12B 112.3(8) . . ? N4B C11B H11C 109.1 . . ? C12B C11B H11C 109.1 . . ? N4B C11B H11D 109.1 . . ? C12B C11B H11D 109.1 . . ? H11C C11B H11D 107.9 . . ? C11B C12B C13B 110.9(8) . . ? C11B C12B H12C 109.5 . . ? C13B C12B H12C 109.5 . . ? C11B C12B H12D 109.5 . . ? C13B C12B H12D 109.5 . . ? H12C C12B H12D 108.1 . . ? C14B C13B C12B 113.8(8) . . ? C14B C13B H13C 108.8 . . ? C12B C13B H13C 108.8 . . ? C14B C13B H13D 108.8 . . ? C12B C13B H13D 108.8 . . ? H13C C13B H13D 107.7 . . ? C13B C14B C13B 114.0(11) 4_565 . ? C13B C14B H14C 108.7 4_565 . ? C13B C14B H14C 108.7 . . ? C13B C14B H14D 108.7 4_565 . ? C13B C14B H14D 108.7 . . ? H14C C14B H14D 107.6 . . ? O7 N6 O8 120.9(13) . . ? O7 N6 O6 118.1(12) . . ? O8 N6 O6 120.9(12) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O7B N6B O6B 119.1(10) . . ? O7B N6B O8B 121.5(13) . . ? O6B N6B O8B 119.4(12) . . ? O9 C17 H17A 109.5 . . ? O9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C17 O9 H9O 108.4 . . ? 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 _geom_hbond_publ_flag O2 H2O O1 1.20 1.28 2.469(8) 166.5 . yes O2 H2O N1 1.20 2.02 3.003(10) 136.2 . yes O5 H5O O6B 0.94 2.05 2.906(10) 150.0 4_565 yes O5 H5O O8B 0.94 2.08 2.885(13) 141.5 4_565 yes O5 H5O N6B 0.94 2.39 3.292(13) 160.7 4_565 yes N3 H3 O7 0.88 2.01 2.871(11) 164.8 1_554 yes N4 H4 O8 0.88 1.99 2.771(11) 146.7 1_655 yes O2B H2P O1B 1.11 1.39 2.446(9) 156.5 . yes O2B H2P N1B 1.11 2.19 2.969(10) 125.0 . yes O5B H5P O7 0.86 1.85 2.602(15) 145.3 . yes O5B H5P O8 0.86 1.94 2.691(14) 146.1 . yes O5B H5P N6 0.86 2.16 3.013(19) 177.1 . yes _diffrn_measured_fraction_theta_max 0.670 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.672 _refine_diff_density_max 1.473 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.115