# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Armando J L Pombeiro' 'Katrin R. Gruenwald' 'Matti Haukka' 'Alexander M Kirillov' 'Joaquin Sanchiz' _publ_contact_author_name 'Armando J L Pombeiro' _publ_contact_author_email POMBEIRO@IST.UTL.PT _publ_section_title ; Mono-, di- and polynuclear copper(II) compounds derived from N-butyldiethanolamine: structural features, magnetism and catalytic activity for the mild peroxidative oxidation of cyclohexane ; # Attachment 'Gruenwald.cif' #Mono-, di- and polynuclear copper(II) compounds derived from #N-butyldiethanolamine: structural features, magnetism and catalytic activity #for the mild peroxidative oxidation of cyclohexane #Katrin R. Gruenwald, Alexander M. Kirillov, Matti Haukka, #Joaquin Sanchiz, Armando J. L. Pombeiro data_1 _database_code_depnum_ccdc_archive 'CCDC 696844' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 Cu N2 O4, 2(C7 H4 N2 O6)' _chemical_formula_sum 'C30 H44 Cu N6 O16' _chemical_formula_weight 808.25 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/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 7.6539(4) _cell_length_b 9.7885(6) _cell_length_c 24.1091(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.234(4) _cell_angle_gamma 90.00 _cell_volume 1803.38(17) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5097 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 26.02 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 0.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8881 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _publ_section_exptl_refinement ; The Cu atom is located on a center of symmetry and is coordinated by four O atoms and two N atoms in a distorted square planar (octahedral) geometry. The OH hydrogen atoms were located from the difference Fourier map or by HYDROGEN (Nardelli, 1999)program map constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogens were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.38 \%A from atom O6 and the deepest hole is located 0.89 \%A from atom Cu1. ; _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 10024 _diffrn_reflns_av_R_equivalents 0.1370 _diffrn_reflns_av_sigmaI/netI 0.1088 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3340 _reflns_number_gt 2458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _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, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0860P)^2^+1.7956P] 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 3340 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1801 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.0000 0.0000 0.5000 0.0245(3) Uani 1 2 d S . . O1 O 0.0987(3) -0.0478(3) 0.59209(10) 0.0309(7) Uani 1 1 d . . . H1O H 0.0154 -0.0378 0.6154 0.046 Uiso 1 1 d R . . O2 O -0.1839(3) 0.1322(3) 0.52097(10) 0.0276(6) Uani 1 1 d . . . O3 O 0.1847(5) 0.5932(4) 0.36013(13) 0.0570(10) Uani 1 1 d . . . O4 O 0.0199(4) 0.4458(3) 0.39810(11) 0.0393(7) Uani 1 1 d . . . O5 O -0.3001(5) 0.1224(5) 0.27946(14) 0.0745(14) Uani 1 1 d . . . O6 O -0.2671(6) 0.1296(5) 0.19141(16) 0.0837(15) Uani 1 1 d . . . O7 O 0.1984(4) 0.3825(3) 0.11618(11) 0.0352(7) Uani 1 1 d . . . H7O H 0.2642 0.3873 0.0868 0.053 Uiso 1 1 d R . . O8 O 0.3802(4) 0.5081(3) 0.17146(12) 0.0423(8) Uani 1 1 d . . . N1 N 0.1722(4) 0.1574(3) 0.51362(12) 0.0278(7) Uani 1 1 d . . . N2 N 0.0931(5) 0.4912(4) 0.35840(14) 0.0354(9) Uani 1 1 d . . . N3 N -0.2246(6) 0.1629(5) 0.23969(17) 0.0631(14) Uani 1 1 d . . . C1 C 0.2340(6) 0.0508(5) 0.60699(17) 0.0357(10) Uani 1 1 d . . . H1A H 0.3277 0.0062 0.6305 0.043 Uiso 1 1 calc R . . H1B H 0.1842 0.1255 0.6288 0.043 Uiso 1 1 calc R . . C2 C 0.3102(5) 0.1092(5) 0.55602(16) 0.0338(10) Uani 1 1 d . . . H2A H 0.3828 0.0386 0.5390 0.041 Uiso 1 1 calc R . . H2B H 0.3874 0.1869 0.5670 0.041 Uiso 1 1 calc R . . C3 C -0.1155(5) 0.2662(4) 0.51106(16) 0.0301(9) Uani 1 1 d . . . H3A H -0.1875 0.3358 0.5289 0.036 Uiso 1 1 calc R . . H3B H -0.1197 0.2847 0.4706 0.036 Uiso 1 1 calc R . . C4 C 0.0698(5) 0.2741(4) 0.53448(17) 0.0329(9) Uani 1 1 d . . . H4A H 0.1230 0.3613 0.5233 0.039 Uiso 1 1 calc R . . H4B H 0.0719 0.2713 0.5756 0.039 Uiso 1 1 calc R . . C5 C 0.2534(5) 0.1903(4) 0.46013(16) 0.0305(9) Uani 1 1 d . . . H5A H 0.1584 0.2163 0.4326 0.037 Uiso 1 1 calc R . . H5B H 0.3074 0.1058 0.4465 0.037 Uiso 1 1 calc R . . C6 C 0.3901(6) 0.3019(5) 0.4612(2) 0.0447(11) Uani 1 1 d . . . H6A H 0.4829 0.2815 0.4903 0.054 Uiso 1 1 calc R . . H6B H 0.3357 0.3902 0.4705 0.054 Uiso 1 1 calc R . . C7 C 0.4705(7) 0.3131(7) 0.4052(2) 0.0610(16) Uani 1 1 d . . . H7A H 0.5484 0.2337 0.4004 0.073 Uiso 1 1 calc R . . H7B H 0.3759 0.3090 0.3755 0.073 Uiso 1 1 calc R . . C8 C 0.5732(8) 0.4417(8) 0.3986(3) 0.084(2) Uani 1 1 d . . . H8A H 0.4976 0.5208 0.4040 0.126 Uiso 1 1 calc R . . H8B H 0.6172 0.4448 0.3612 0.126 Uiso 1 1 calc R . . H8C H 0.6720 0.4436 0.4263 0.126 Uiso 1 1 calc R . . C9 C 0.0719(5) 0.4182(4) 0.30478(16) 0.0292(9) Uani 1 1 d . . . C10 C -0.0548(5) 0.3182(5) 0.30005(17) 0.0337(10) Uani 1 1 d . . . H10 H -0.1206 0.2915 0.3305 0.040 Uiso 1 1 calc R . . C11 C -0.0796(6) 0.2596(5) 0.24846(18) 0.0389(11) Uani 1 1 d . . . C12 C 0.0192(5) 0.2919(5) 0.20427(17) 0.0354(10) Uani 1 1 d . . . H12 H -0.0005 0.2466 0.1696 0.042 Uiso 1 1 calc R . . C13 C 0.1471(5) 0.3909(4) 0.21084(16) 0.0292(9) Uani 1 1 d . . . C14 C 0.1730(5) 0.4562(5) 0.26198(16) 0.0307(9) Uani 1 1 d . . . H14 H 0.2589 0.5258 0.2672 0.037 Uiso 1 1 calc R . . C15 C 0.2532(5) 0.4321(5) 0.16211(16) 0.0312(9) Uani 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 0.0262(4) 0.0245(4) 0.0235(4) -0.0006(3) 0.0070(2) 0.0015(3) O1 0.0328(15) 0.0338(16) 0.0268(13) -0.0013(13) 0.0087(11) -0.0002(13) O2 0.0318(14) 0.0247(15) 0.0270(13) -0.0007(12) 0.0078(11) 0.0011(12) O3 0.079(2) 0.050(2) 0.0435(18) -0.0128(17) 0.0205(17) -0.026(2) O4 0.0546(19) 0.0378(18) 0.0271(14) 0.0004(14) 0.0175(13) 0.0006(15) O5 0.082(3) 0.105(4) 0.0372(18) 0.008(2) 0.0138(18) -0.059(3) O6 0.110(3) 0.092(3) 0.051(2) -0.023(2) 0.022(2) -0.060(3) O7 0.0418(17) 0.0397(19) 0.0255(14) 0.0004(13) 0.0137(12) -0.0049(14) O8 0.0422(17) 0.054(2) 0.0325(15) -0.0039(14) 0.0147(13) -0.0164(15) N1 0.0322(17) 0.0249(18) 0.0272(16) -0.0015(14) 0.0090(13) 0.0043(14) N2 0.044(2) 0.033(2) 0.0301(18) -0.0021(16) 0.0138(16) 0.0018(17) N3 0.082(3) 0.069(3) 0.040(2) -0.008(2) 0.018(2) -0.040(3) C1 0.041(2) 0.036(2) 0.030(2) -0.0011(19) 0.0031(18) -0.004(2) C2 0.031(2) 0.035(2) 0.035(2) 0.0000(19) -0.0019(17) -0.0011(18) C3 0.035(2) 0.023(2) 0.033(2) 0.0002(18) 0.0095(17) 0.0033(17) C4 0.034(2) 0.028(2) 0.037(2) -0.0057(19) 0.0131(17) 0.0008(18) C5 0.033(2) 0.030(2) 0.029(2) 0.0034(18) 0.0129(16) -0.0008(17) C6 0.040(3) 0.039(3) 0.057(3) 0.007(2) 0.015(2) -0.004(2) C7 0.039(3) 0.070(4) 0.076(4) 0.033(3) 0.021(2) 0.008(3) C8 0.053(3) 0.075(5) 0.126(6) 0.046(4) 0.033(4) -0.001(3) C9 0.032(2) 0.029(2) 0.0273(19) 0.0004(18) 0.0080(16) 0.0042(17) C10 0.036(2) 0.036(3) 0.030(2) 0.0050(18) 0.0117(17) 0.0020(19) C11 0.042(2) 0.039(3) 0.037(2) -0.005(2) 0.0104(19) -0.013(2) C12 0.042(2) 0.037(3) 0.028(2) -0.0019(19) 0.0090(18) -0.003(2) C13 0.029(2) 0.030(2) 0.029(2) 0.0026(18) 0.0080(16) 0.0032(18) C14 0.032(2) 0.030(2) 0.031(2) 0.0009(18) 0.0079(16) 0.0005(18) C15 0.035(2) 0.032(2) 0.028(2) 0.0022(18) 0.0121(17) 0.0027(19) _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 O2 1.998(3) 3_556 ? Cu1 O2 1.998(3) . yes Cu1 N1 2.042(3) . yes Cu1 N1 2.042(3) 3_556 ? Cu1 O1 2.352(3) 3_556 ? Cu1 O1 2.352(3) . yes O1 C1 1.446(5) . ? O1 H1O 0.8777 . ? O2 C3 1.437(5) . ? O3 N2 1.219(5) . yes O4 N2 1.220(4) . yes O5 N3 1.213(5) . yes O6 N3 1.235(5) . yes O7 C15 1.259(5) . yes O7 H7O 0.8935 . ? O8 C15 1.235(5) . yes N1 C4 1.489(5) . ? N1 C5 1.498(5) . ? N1 C2 1.504(5) . ? N2 C9 1.478(5) . ? N3 C11 1.465(6) . ? C1 C2 1.503(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.499(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.512(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.521(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.497(9) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.375(6) . ? C9 C10 1.378(6) . ? C10 C11 1.373(6) . ? C10 H10 0.9500 . ? C11 C12 1.378(6) . ? C12 C13 1.380(6) . ? C12 H12 0.9500 . ? C13 C14 1.393(6) . ? C13 C15 1.520(5) . ? C14 H14 0.9500 . ? 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 O2 Cu1 O2 179.999(1) 3_556 . ? O2 Cu1 N1 94.12(12) 3_556 . ? O2 Cu1 N1 85.88(12) . . yes O2 Cu1 N1 85.88(12) 3_556 3_556 ? O2 Cu1 N1 94.12(12) . 3_556 ? N1 Cu1 N1 180.0 . 3_556 ? O2 Cu1 O1 94.78(10) 3_556 3_556 ? O2 Cu1 O1 85.22(10) . 3_556 ? N1 Cu1 O1 99.89(11) . 3_556 ? N1 Cu1 O1 80.11(11) 3_556 3_556 ? O2 Cu1 O1 85.22(10) 3_556 . ? O2 Cu1 O1 94.78(10) . . yes N1 Cu1 O1 80.11(11) . . ? N1 Cu1 O1 99.89(11) 3_556 . ? O1 Cu1 O1 179.998(1) 3_556 . ? C1 O1 Cu1 106.8(2) . . ? C1 O1 H1O 107.6 . . ? Cu1 O1 H1O 112.0 . . ? C3 O2 Cu1 106.3(2) . . ? C15 O7 H7O 120.2 . . ? C4 N1 C5 112.2(3) . . ? C4 N1 C2 112.0(3) . . ? C5 N1 C2 110.1(3) . . ? C4 N1 Cu1 106.6(2) . . ? C5 N1 Cu1 108.6(2) . . ? C2 N1 Cu1 107.1(3) . . ? O3 N2 O4 124.1(4) . . yes O3 N2 C9 117.4(3) . . ? O4 N2 C9 118.5(4) . . ? O5 N3 O6 123.2(4) . . yes O5 N3 C11 119.2(4) . . ? O6 N3 C11 117.6(4) . . ? O1 C1 C2 110.9(3) . . ? O1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C1 C2 N1 112.6(3) . . ? C1 C2 H2A 109.1 . . ? N1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? N1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? O2 C3 C4 109.3(3) . . ? O2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? O2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? N1 C4 C3 109.7(3) . . ? N1 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N1 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N1 C5 C6 117.4(4) . . ? N1 C5 H5A 107.9 . . ? C6 C5 H5A 107.9 . . ? N1 C5 H5B 107.9 . . ? C6 C5 H5B 107.9 . . ? H5A C5 H5B 107.2 . . ? C5 C6 C7 110.5(4) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 113.3(6) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? 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 . . ? C14 C9 C10 123.6(4) . . ? C14 C9 N2 119.1(4) . . ? C10 C9 N2 117.2(4) . . ? C11 C10 C9 115.6(4) . . ? C11 C10 H10 122.2 . . ? C9 C10 H10 122.2 . . ? C10 C11 C12 123.4(4) . . ? C10 C11 N3 117.8(4) . . ? C12 C11 N3 118.8(4) . . ? C11 C12 C13 119.3(4) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C14 119.2(4) . . ? C12 C13 C15 120.3(4) . . ? C14 C13 C15 120.5(4) . . ? C9 C14 C13 118.8(4) . . ? C9 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? O8 C15 O7 127.8(4) . . yes O8 C15 C13 117.9(4) . . ? O7 C15 C13 114.3(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 O1 H1O O8 0.88 1.77 2.640(4) 169.1 4_566 yes O7 H7O O2 0.89 1.67 2.517(3) 157.4 4_665 yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.119 _refine_diff_density_min -0.900 _refine_diff_density_rms 0.106 #===END======================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 696845' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 Cu2 N8 O4' _chemical_formula_sum 'C16 H36 Cu2 N8 O4' _chemical_formula_weight 531.61 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 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 26.5312(6) _cell_length_b 13.8357(3) _cell_length_c 12.6742(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.0030(10) _cell_angle_gamma 90.00 _cell_volume 4641.07(18) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 18323 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description green _exptl_crystal_colour plate _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 1.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6449 _exptl_absorpt_correction_T_max 0.8350 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The Cu atom is located coordinated by four O atoms and a N atom in a distorted square based pyramidal geometry. The idealized positions of the H~2~O and OH hydrogens were estimated with HYDROGEN (Nardelli, 1999)program and constrained to ride on their parent atom with U~iso~ = 1.5 (parent atom). Other hydrogens were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.68 \%A from atom H16C and the deepest hole is located 0.80 \%A from atom Cu1. ; _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 39037 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.45 _reflns_number_total 10111 _reflns_number_gt 9020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0372P)^2^+0.0205P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.039(7) _chemical_absolute_configuration unk _refine_ls_number_reflns 10111 _refine_ls_number_parameters 547 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.008 _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 0.338508(14) 0.81382(3) 0.22270(3) 0.01375(9) Uani 1 1 d . . . Cu2 Cu 0.373865(14) 0.70130(3) 0.04373(3) 0.01367(9) Uani 1 1 d . . . O1 O 0.40100(8) 0.83815(16) 0.35574(17) 0.0197(5) Uani 1 1 d . . . H1O H 0.4335 0.8396 0.3596 0.030 Uiso 1 1 d R . . O2 O 0.35822(8) 0.67966(15) 0.19018(17) 0.0141(5) Uani 1 1 d . . . O3 O 0.37489(8) 0.83733(15) 0.09559(17) 0.0145(5) Uani 1 1 d . . . O4 O 0.46076(8) 0.68626(16) 0.05062(17) 0.0196(5) Uani 1 1 d . . . H4O H 0.4769 0.6988 0.1071 0.029 Uiso 1 1 d . . . N1 N 0.30443(11) 0.9370(2) 0.2362(2) 0.0250(6) Uani 1 1 d . . . N2 N 0.31605(10) 1.0105(2) 0.1939(2) 0.0195(6) Uani 1 1 d . . . N3 N 0.32598(14) 1.0830(2) 0.1545(2) 0.0334(8) Uani 1 1 d . . . N4 N 0.35844(11) 0.5742(2) -0.0153(2) 0.0234(6) Uani 1 1 d . . . N5 N 0.35963(10) 0.5005(2) 0.0351(2) 0.0222(6) Uani 1 1 d . . . N6 N 0.35936(13) 0.4269(2) 0.0784(2) 0.0352(8) Uani 1 1 d . . . N7 N 0.30216(10) 0.75199(19) 0.3422(2) 0.0166(6) Uani 1 1 d . . . N8 N 0.38506(9) 0.76140(19) -0.0990(2) 0.0149(5) Uani 1 1 d . . . C1 C 0.38406(12) 0.7873(2) 0.4464(3) 0.0204(7) Uani 1 1 d . . . H1A H 0.3987 0.8176 0.5125 0.024 Uiso 1 1 calc R . . H1B H 0.3953 0.7191 0.4453 0.024 Uiso 1 1 calc R . . C2 C 0.32727(12) 0.7920(2) 0.4424(3) 0.0188(7) Uani 1 1 d . . . H2A H 0.3154 0.7555 0.5031 0.023 Uiso 1 1 calc R . . H2B H 0.3168 0.8602 0.4500 0.023 Uiso 1 1 calc R . . C3 C 0.32051(12) 0.6157(2) 0.2239(2) 0.0180(7) Uani 1 1 d . . . H3A H 0.3326 0.5480 0.2228 0.022 Uiso 1 1 calc R . . H3B H 0.2893 0.6209 0.1765 0.022 Uiso 1 1 calc R . . C4 C 0.31004(12) 0.6453(2) 0.3364(3) 0.0167(7) Uani 1 1 d . . . H4A H 0.2796 0.6114 0.3579 0.020 Uiso 1 1 calc R . . H4B H 0.3389 0.6264 0.3857 0.020 Uiso 1 1 calc R . . C5 C 0.24744(12) 0.7781(2) 0.3400(3) 0.0191(7) Uani 1 1 d . . . H5A H 0.2444 0.8490 0.3484 0.023 Uiso 1 1 calc R . . H5B H 0.2324 0.7472 0.4008 0.023 Uiso 1 1 calc R . . C6 C 0.21730(12) 0.7476(2) 0.2380(3) 0.0196(7) Uani 1 1 d . . . H6A H 0.2351 0.7695 0.1763 0.024 Uiso 1 1 calc R . . H6B H 0.2150 0.6762 0.2353 0.024 Uiso 1 1 calc R . . C7 C 0.16434(13) 0.7905(3) 0.2322(3) 0.0289(8) Uani 1 1 d . . . H7A H 0.1668 0.8618 0.2300 0.035 Uiso 1 1 calc R . . H7B H 0.1476 0.7725 0.2967 0.035 Uiso 1 1 calc R . . C8 C 0.13221(15) 0.7553(3) 0.1351(3) 0.0397(10) Uani 1 1 d . . . H8A H 0.1483 0.7743 0.0709 0.060 Uiso 1 1 calc R . . H8B H 0.0985 0.7844 0.1345 0.060 Uiso 1 1 calc R . . H8C H 0.1292 0.6848 0.1376 0.060 Uiso 1 1 calc R . . C9 C 0.35604(12) 0.8966(2) 0.0088(2) 0.0183(7) Uani 1 1 d . . . H9A H 0.3616 0.9658 0.0262 0.022 Uiso 1 1 calc R . . H9B H 0.3193 0.8858 -0.0060 0.022 Uiso 1 1 calc R . . C10 C 0.38422(12) 0.8693(2) -0.0866(2) 0.0158(6) Uani 1 1 d . . . H10A H 0.3675 0.8991 -0.1509 0.019 Uiso 1 1 calc R . . H10B H 0.4193 0.8942 -0.0778 0.019 Uiso 1 1 calc R . . C11 C 0.47630(12) 0.7395(2) -0.0379(3) 0.0177(7) Uani 1 1 d . . . H11A H 0.5089 0.7144 -0.0597 0.021 Uiso 1 1 calc R . . H11B H 0.4806 0.8086 -0.0191 0.021 Uiso 1 1 calc R . . C12 C 0.43588(11) 0.7280(2) -0.1268(3) 0.0172(6) Uani 1 1 d . . . H12A H 0.4458 0.7651 -0.1888 0.021 Uiso 1 1 calc R . . H12B H 0.4337 0.6591 -0.1474 0.021 Uiso 1 1 calc R . . C13 C 0.34806(12) 0.7273(2) -0.1856(3) 0.0180(7) Uani 1 1 d . . . H13A H 0.3510 0.6562 -0.1919 0.022 Uiso 1 1 calc R . . H13B H 0.3572 0.7560 -0.2532 0.022 Uiso 1 1 calc R . . C14 C 0.29354(11) 0.7526(2) -0.1690(3) 0.0206(7) Uani 1 1 d . . . H14A H 0.2891 0.8236 -0.1715 0.025 Uiso 1 1 calc R . . H14B H 0.2848 0.7298 -0.0985 0.025 Uiso 1 1 calc R . . C15 C 0.25834(13) 0.7053(3) -0.2548(3) 0.0318(9) Uani 1 1 d . . . H15A H 0.2710 0.7189 -0.3250 0.038 Uiso 1 1 calc R . . H15B H 0.2587 0.6344 -0.2444 0.038 Uiso 1 1 calc R . . C16 C 0.20429(14) 0.7418(3) -0.2531(4) 0.0472(12) Uani 1 1 d . . . H16A H 0.1921 0.7310 -0.1828 0.071 Uiso 1 1 calc R . . H16B H 0.1827 0.7069 -0.3061 0.071 Uiso 1 1 calc R . . H16C H 0.2033 0.8111 -0.2693 0.071 Uiso 1 1 calc R . . Cu1B Cu 0.518467(14) 0.66979(3) 0.35071(3) 0.01304(9) Uani 1 1 d . . . Cu2B Cu 0.540100(14) 0.84655(3) 0.23189(3) 0.01329(9) Uani 1 1 d . . . O1B O 0.44080(8) 0.61450(15) 0.29867(18) 0.0193(5) Uani 1 1 d . . . H1P H 0.4139 0.6407 0.2701 0.029 Uiso 1 1 d R . . O2B O 0.53482(8) 0.70744(15) 0.20606(17) 0.0148(5) Uani 1 1 d . . . O3B O 0.50402(8) 0.80831(14) 0.35611(17) 0.0140(5) Uani 1 1 d . . . O4B O 0.46822(8) 0.91231(15) 0.14191(17) 0.0184(5) Uani 1 1 d . . . H4P H 0.4393 0.8888 0.1211 0.028 Uiso 1 1 d . . . N1B N 0.51963(11) 0.6355(2) 0.4990(2) 0.0222(6) Uani 1 1 d . . . N2B N 0.50195(11) 0.68151(19) 0.5676(2) 0.0192(6) Uani 1 1 d . . . N3B N 0.48619(13) 0.7222(2) 0.6375(2) 0.0326(7) Uani 1 1 d . . . N4B N 0.58522(10) 0.8828(2) 0.1249(2) 0.0218(6) Uani 1 1 d . . . N5B N 0.59924(11) 0.8319(2) 0.0561(2) 0.0201(6) Uani 1 1 d . . . N6B N 0.61378(13) 0.7870(2) -0.0120(3) 0.0349(8) Uani 1 1 d . . . N7B N 0.54007(9) 0.53451(19) 0.3074(2) 0.0140(5) Uani 1 1 d . . . N8B N 0.54200(9) 0.98091(18) 0.29969(19) 0.0133(5) Uani 1 1 d . . . C1B C 0.44771(12) 0.5211(2) 0.2524(3) 0.0202(7) Uani 1 1 d . . . H1B1 H 0.4530 0.5279 0.1762 0.024 Uiso 1 1 calc R . . H1B2 H 0.4174 0.4805 0.2598 0.024 Uiso 1 1 calc R . . C2B C 0.49365(11) 0.4749(2) 0.3099(3) 0.0168(6) Uani 1 1 d . . . H2B1 H 0.4865 0.4636 0.3845 0.020 Uiso 1 1 calc R . . H2B2 H 0.4998 0.4113 0.2774 0.020 Uiso 1 1 calc R . . C3B C 0.57337(12) 0.6444(2) 0.1738(2) 0.0164(6) Uani 1 1 d . . . H3B1 H 0.6059 0.6592 0.2133 0.020 Uiso 1 1 calc R . . H3B2 H 0.5776 0.6523 0.0973 0.020 Uiso 1 1 calc R . . C4B C 0.55707(12) 0.5419(2) 0.1969(2) 0.0182(7) Uani 1 1 d . . . H4B1 H 0.5291 0.5227 0.1455 0.022 Uiso 1 1 calc R . . H4B2 H 0.5857 0.4971 0.1890 0.022 Uiso 1 1 calc R . . C5B C 0.57943(11) 0.4883(2) 0.3810(2) 0.0167(6) Uani 1 1 d . . . H5B1 H 0.5852 0.4216 0.3564 0.020 Uiso 1 1 calc R . . H5B2 H 0.5663 0.4839 0.4520 0.020 Uiso 1 1 calc R . . C6B C 0.62990(12) 0.5410(2) 0.3910(3) 0.0198(7) Uani 1 1 d . . . H6B1 H 0.6244 0.6097 0.4086 0.024 Uiso 1 1 calc R . . H6B2 H 0.6458 0.5383 0.3227 0.024 Uiso 1 1 calc R . . C7B C 0.66487(12) 0.4943(3) 0.4774(3) 0.0268(8) Uani 1 1 d . . . H7B1 H 0.6503 0.5033 0.5466 0.032 Uiso 1 1 calc R . . H7B2 H 0.6669 0.4240 0.4638 0.032 Uiso 1 1 calc R . . C8B C 0.71807(13) 0.5370(3) 0.4829(3) 0.0350(9) Uani 1 1 d . . . H8B1 H 0.7341 0.5218 0.4176 0.053 Uiso 1 1 calc R . . H8B2 H 0.7381 0.5093 0.5434 0.053 Uiso 1 1 calc R . . H8B3 H 0.7161 0.6073 0.4912 0.053 Uiso 1 1 calc R . . C9B C 0.51913(12) 0.8704(2) 0.4429(2) 0.0155(6) Uani 1 1 d . . . H9B1 H 0.5539 0.8546 0.4709 0.019 Uiso 1 1 calc R . . H9B2 H 0.4961 0.8624 0.5006 0.019 Uiso 1 1 calc R . . C10B C 0.51674(12) 0.9737(2) 0.4015(3) 0.0169(7) Uani 1 1 d . . . H10C H 0.4810 0.9941 0.3900 0.020 Uiso 1 1 calc R . . H10D H 0.5337 1.0175 0.4546 0.020 Uiso 1 1 calc R . . C11B C 0.46107(12) 1.0058(2) 0.1866(3) 0.0191(7) Uani 1 1 d . . . H11C H 0.4396 1.0008 0.2472 0.023 Uiso 1 1 calc R . . H11D H 0.4442 1.0493 0.1331 0.023 Uiso 1 1 calc R . . C12B C 0.51289(12) 1.0454(2) 0.2233(3) 0.0188(7) Uani 1 1 d . . . H12C H 0.5327 1.0554 0.1608 0.023 Uiso 1 1 calc R . . H12D H 0.5086 1.1091 0.2570 0.023 Uiso 1 1 calc R . . C13B C 0.59396(12) 1.0213(2) 0.3159(3) 0.0181(7) Uani 1 1 d . . . H13C H 0.5916 1.0892 0.3397 0.022 Uiso 1 1 calc R . . H13D H 0.6096 1.0217 0.2472 0.022 Uiso 1 1 calc R . . C14B C 0.62858(11) 0.9661(2) 0.3962(3) 0.0195(7) Uani 1 1 d . . . H14C H 0.6155 0.9720 0.4672 0.023 Uiso 1 1 calc R . . H14D H 0.6286 0.8968 0.3770 0.023 Uiso 1 1 calc R . . C15B C 0.68225(12) 1.0048(3) 0.3996(3) 0.0285(8) Uani 1 1 d . . . H15C H 0.6816 1.0760 0.4079 0.034 Uiso 1 1 calc R . . H15D H 0.6970 0.9901 0.3319 0.034 Uiso 1 1 calc R . . C16B C 0.71569(14) 0.9607(3) 0.4910(4) 0.0466(12) Uani 1 1 d . . . H16D H 0.7050 0.9852 0.5585 0.070 Uiso 1 1 calc R . . H16E H 0.7510 0.9786 0.4837 0.070 Uiso 1 1 calc R . . H16F H 0.7124 0.8902 0.4893 0.070 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 0.01324(18) 0.01485(19) 0.01320(19) 0.00006(16) 0.00117(15) 0.00062(15) Cu2 0.01387(18) 0.01430(19) 0.01277(18) -0.00049(15) 0.00038(14) -0.00003(15) O1 0.0134(11) 0.0254(12) 0.0199(12) 0.0022(10) -0.0010(9) -0.0033(9) O2 0.0132(11) 0.0146(11) 0.0144(11) -0.0006(9) 0.0003(9) -0.0011(8) O3 0.0169(11) 0.0130(11) 0.0135(11) 0.0016(9) 0.0005(9) 0.0008(9) O4 0.0160(11) 0.0254(12) 0.0164(12) 0.0010(9) -0.0050(9) -0.0002(9) N1 0.0265(16) 0.0221(15) 0.0273(16) 0.0023(13) 0.0080(12) 0.0024(12) N2 0.0220(14) 0.0196(16) 0.0166(14) -0.0033(12) -0.0003(11) 0.0037(11) N3 0.059(2) 0.0180(16) 0.0236(16) -0.0016(13) 0.0028(15) -0.0008(15) N4 0.0340(17) 0.0179(15) 0.0175(14) -0.0014(12) -0.0033(12) -0.0041(12) N5 0.0249(16) 0.0211(16) 0.0194(14) -0.0067(14) -0.0064(12) -0.0020(11) N6 0.059(2) 0.0209(17) 0.0240(17) 0.0007(14) -0.0103(15) -0.0008(15) N7 0.0161(13) 0.0191(14) 0.0146(14) 0.0002(11) 0.0002(11) -0.0007(11) N8 0.0136(13) 0.0161(14) 0.0148(14) -0.0013(11) -0.0005(11) 0.0024(10) C1 0.0207(17) 0.0257(17) 0.0144(16) 0.0008(14) -0.0017(13) -0.0032(13) C2 0.0157(16) 0.0259(18) 0.0149(16) -0.0028(14) 0.0021(12) -0.0036(13) C3 0.0131(15) 0.0222(17) 0.0184(17) 0.0006(14) -0.0002(12) -0.0034(12) C4 0.0156(16) 0.0197(16) 0.0149(16) 0.0034(13) 0.0024(13) -0.0002(13) C5 0.0125(15) 0.0245(17) 0.0205(17) 0.0000(14) 0.0024(12) 0.0009(13) C6 0.0137(15) 0.0263(18) 0.0190(17) -0.0030(14) 0.0018(12) 0.0000(13) C7 0.0138(16) 0.039(2) 0.034(2) 0.0023(17) 0.0003(14) 0.0065(14) C8 0.026(2) 0.049(3) 0.043(2) 0.006(2) -0.0134(17) 0.0009(18) C9 0.0211(16) 0.0164(17) 0.0174(16) 0.0024(14) 0.0006(13) 0.0037(13) C10 0.0175(15) 0.0144(16) 0.0155(16) 0.0035(13) 0.0003(12) 0.0022(12) C11 0.0125(15) 0.0200(16) 0.0205(17) -0.0011(14) 0.0011(13) 0.0016(12) C12 0.0108(14) 0.0241(17) 0.0167(16) -0.0047(13) 0.0008(12) 0.0011(12) C13 0.0164(16) 0.0226(17) 0.0142(16) -0.0034(13) -0.0039(12) -0.0020(13) C14 0.0137(15) 0.0266(18) 0.0210(17) 0.0003(14) -0.0031(13) 0.0014(13) C15 0.0197(18) 0.045(2) 0.030(2) -0.0097(18) -0.0063(15) -0.0001(16) C16 0.0178(19) 0.066(3) 0.056(3) -0.015(2) -0.0122(18) 0.0021(19) Cu1B 0.01373(18) 0.01282(18) 0.01241(19) 0.00008(16) -0.00008(15) -0.00002(15) Cu2B 0.01381(18) 0.01232(18) 0.01371(19) 0.00004(16) 0.00073(15) -0.00036(15) O1B 0.0135(11) 0.0171(11) 0.0264(12) 0.0001(10) -0.0058(9) 0.0032(9) O2B 0.0139(11) 0.0143(11) 0.0163(12) -0.0013(9) 0.0019(9) 0.0000(9) O3B 0.0163(11) 0.0126(11) 0.0130(11) -0.0021(9) -0.0006(9) 0.0006(8) O4B 0.0139(10) 0.0170(11) 0.0237(12) -0.0037(9) -0.0039(9) -0.0013(8) N1B 0.0321(16) 0.0182(14) 0.0162(14) 0.0030(12) 0.0017(12) 0.0050(12) N2B 0.0221(14) 0.0198(14) 0.0155(15) 0.0069(12) 0.0008(12) -0.0021(11) N3B 0.048(2) 0.0290(17) 0.0230(17) -0.0013(14) 0.0145(15) 0.0026(15) N4B 0.0238(15) 0.0202(15) 0.0223(15) 0.0002(13) 0.0082(12) -0.0006(12) N5B 0.0211(14) 0.0212(15) 0.0184(15) 0.0055(13) 0.0040(12) 0.0007(12) N6B 0.051(2) 0.0261(17) 0.0300(18) 0.0004(14) 0.0194(17) 0.0009(15) N7B 0.0117(13) 0.0162(13) 0.0139(13) 0.0005(11) -0.0012(10) 0.0001(10) N8B 0.0137(13) 0.0107(13) 0.0150(14) 0.0012(10) -0.0023(10) 0.0001(10) C1B 0.0176(17) 0.0171(16) 0.0253(18) -0.0005(14) -0.0037(13) -0.0046(13) C2B 0.0142(15) 0.0126(15) 0.0232(17) -0.0005(13) -0.0009(13) -0.0022(12) C3B 0.0175(16) 0.0155(16) 0.0165(16) -0.0012(13) 0.0036(13) 0.0027(12) C4B 0.0213(16) 0.0166(16) 0.0166(17) -0.0037(13) 0.0013(13) 0.0008(13) C5B 0.0167(16) 0.0150(15) 0.0178(16) 0.0034(13) -0.0028(12) 0.0032(12) C6B 0.0146(15) 0.0223(17) 0.0222(17) 0.0027(14) -0.0011(13) 0.0024(13) C7B 0.0139(16) 0.036(2) 0.0292(19) 0.0054(17) -0.0047(14) -0.0017(14) C8B 0.0217(19) 0.041(2) 0.041(2) 0.0042(19) -0.0079(16) -0.0016(16) C9B 0.0182(16) 0.0137(16) 0.0140(16) -0.0033(13) -0.0015(12) 0.0003(12) C10B 0.0178(15) 0.0132(16) 0.0193(16) -0.0039(13) -0.0008(13) 0.0010(12) C11B 0.0203(16) 0.0173(17) 0.0196(17) 0.0003(13) 0.0000(13) 0.0048(13) C12B 0.0210(16) 0.0132(15) 0.0213(17) 0.0033(13) -0.0039(13) -0.0007(12) C13B 0.0155(15) 0.0172(16) 0.0214(16) -0.0005(13) -0.0005(13) -0.0029(12) C14B 0.0151(15) 0.0226(17) 0.0202(16) 0.0020(14) -0.0022(13) -0.0021(12) C15B 0.0175(17) 0.030(2) 0.037(2) 0.0049(17) -0.0029(15) -0.0032(14) C16B 0.022(2) 0.059(3) 0.058(3) 0.022(2) -0.0108(19) -0.0064(19) _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 1.942(3) . yes Cu1 O3 1.962(2) . yes Cu1 O2 1.980(2) . yes Cu1 N7 2.039(3) . yes Cu1 O1 2.305(2) . yes Cu1 Cu2 2.9574(5) . yes Cu2 N4 1.944(3) . yes Cu2 O2 1.953(2) . yes Cu2 O3 1.993(2) . yes Cu2 N8 2.031(3) . yes Cu2 O4 2.310(2) . yes O1 C1 1.446(4) . ? O1 H1O 0.8595 . ? O2 C3 1.424(4) . ? O3 C9 1.434(4) . ? O4 C11 1.427(4) . ? O4 H4O 0.8271 . ? N1 N2 1.201(4) . yes N2 N3 1.158(4) . yes N4 N5 1.202(4) . yes N5 N6 1.157(4) . yes N7 C4 1.493(4) . ? N7 C5 1.495(4) . ? N7 C2 1.499(4) . ? N8 C12 1.491(4) . ? N8 C13 1.497(4) . ? N8 C10 1.502(4) . ? C1 C2 1.505(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.531(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.526(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.513(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.509(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.517(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.531(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.522(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? Cu1B N1B 1.936(3) . yes Cu1B O3B 1.957(2) . yes Cu1B O2B 1.983(2) . yes Cu1B N7B 2.044(3) . yes Cu1B O1B 2.253(2) . yes Cu1B Cu2B 2.9495(5) . yes Cu2B N4B 1.936(3) . yes Cu2B O2B 1.956(2) . yes Cu2B O3B 1.971(2) . yes Cu2B N8B 2.047(3) . yes Cu2B O4B 2.337(2) . yes O1B C1B 1.436(4) . ? O1B H1P 0.8573 . ? O2B C3B 1.426(4) . ? O3B C9B 1.431(4) . ? O4B C11B 1.430(4) . ? O4B H4P 0.8573 . ? N1B N2B 1.199(4) . yes N2B N3B 1.153(4) . yes N4B N5B 1.200(4) . yes N5B N6B 1.152(4) . yes N7B C2B 1.484(4) . ? N7B C5B 1.495(4) . ? N7B C4B 1.504(4) . ? N8B C13B 1.489(4) . ? N8B C12B 1.491(4) . ? N8B C10B 1.499(4) . ? C1B C2B 1.517(4) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.517(4) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.522(4) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.528(4) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C8B 1.527(5) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 0.9800 . ? C9B C10B 1.522(4) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B C12B 1.522(4) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.527(4) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C15B 1.519(4) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15B C16B 1.536(5) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 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 O3 100.70(11) . . yes N1 Cu1 O2 166.50(11) . . yes O3 Cu1 O2 80.34(9) . . yes N1 Cu1 N7 93.17(11) . . yes O3 Cu1 N7 164.67(10) . . ? O2 Cu1 N7 84.65(10) . . ? N1 Cu1 O1 97.06(11) . . yes O3 Cu1 O1 101.92(9) . . ? O2 Cu1 O1 95.87(8) . . ? N7 Cu1 O1 82.62(9) . . ? N1 Cu1 Cu2 134.75(9) . . ? O3 Cu1 Cu2 42.01(6) . . ? O2 Cu1 Cu2 40.90(6) . . ? N7 Cu1 Cu2 122.71(7) . . ? O1 Cu1 Cu2 112.80(6) . . ? N4 Cu2 O2 100.03(10) . . yes N4 Cu2 O3 168.26(11) . . yes O2 Cu2 O3 80.22(9) . . yes N4 Cu2 N8 93.88(11) . . yes O2 Cu2 N8 164.35(9) . . ? O3 Cu2 N8 84.70(10) . . ? N4 Cu2 O4 96.65(10) . . yes O2 Cu2 O4 103.18(9) . . ? O3 Cu2 O4 94.70(8) . . ? N8 Cu2 O4 82.12(9) . . ? N4 Cu2 Cu1 134.60(9) . . ? O2 Cu2 Cu1 41.58(6) . . ? O3 Cu2 Cu1 41.21(6) . . ? N8 Cu2 Cu1 122.78(7) . . ? O4 Cu2 Cu1 112.80(6) . . ? C1 O1 Cu1 105.25(17) . . ? C1 O1 H1O 109.4 . . ? Cu1 O1 H1O 135.3 . . ? C3 O2 Cu2 125.50(19) . . ? C3 O2 Cu1 108.62(18) . . ? Cu2 O2 Cu1 97.52(9) . . ? C9 O3 Cu1 124.01(18) . . ? C9 O3 Cu2 106.95(18) . . ? Cu1 O3 Cu2 96.79(9) . . ? C11 O4 Cu2 105.45(17) . . ? C11 O4 H4O 114.3 . . ? Cu2 O4 H4O 118.0 . . ? N2 N1 Cu1 124.7(2) . . ? N3 N2 N1 177.8(4) . . yes N5 N4 Cu2 124.4(2) . . ? N6 N5 N4 175.9(3) . . yes C4 N7 C5 112.2(2) . . ? C4 N7 C2 110.6(2) . . ? C5 N7 C2 107.5(2) . . ? C4 N7 Cu1 107.63(19) . . ? C5 N7 Cu1 113.19(19) . . ? C2 N7 Cu1 105.61(19) . . ? C12 N8 C13 106.6(2) . . ? C12 N8 C10 110.7(2) . . ? C13 N8 C10 112.1(2) . . ? C12 N8 Cu2 105.97(18) . . ? C13 N8 Cu2 113.3(2) . . ? C10 N8 Cu2 108.04(18) . . ? O1 C1 C2 108.5(3) . . ? O1 C1 H1A 110.0 . . ? C2 C1 H1A 110.0 . . ? O1 C1 H1B 110.0 . . ? C2 C1 H1B 110.0 . . ? H1A C1 H1B 108.4 . . ? N7 C2 C1 113.4(3) . . ? N7 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N7 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? O2 C3 C4 106.9(2) . . ? O2 C3 H3A 110.4 . . ? C4 C3 H3A 110.4 . . ? O2 C3 H3B 110.4 . . ? C4 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? N7 C4 C3 110.3(3) . . ? N7 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N7 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? N7 C5 C6 113.5(3) . . ? N7 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N7 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 111.1(3) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 112.1(3) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? 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 . . ? O3 C9 C10 107.7(2) . . ? O3 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? O3 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? N8 C10 C9 110.1(2) . . ? N8 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N8 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.2 . . ? O4 C11 C12 107.7(2) . . ? O4 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? O4 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? N8 C12 C11 113.4(2) . . ? N8 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? N8 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N8 C13 C14 114.1(3) . . ? N8 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? N8 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C15 110.1(3) . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 C14 112.1(3) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1B Cu1B O3B 101.29(11) . . yes N1B Cu1B O2B 166.40(11) . . yes O3B Cu1B O2B 80.28(9) . . yes N1B Cu1B N7B 92.92(11) . . yes O3B Cu1B N7B 164.95(10) . . ? O2B Cu1B N7B 84.75(9) . . ? N1B Cu1B O1B 98.82(11) . . yes O3B Cu1B O1B 99.52(8) . . ? O2B Cu1B O1B 94.20(9) . . ? N7B Cu1B O1B 83.01(9) . . ? N1B Cu1B Cu2B 135.08(9) . . ? O3B Cu1B Cu2B 41.52(7) . . ? O2B Cu1B Cu2B 41.16(6) . . ? N7B Cu1B Cu2B 123.63(7) . . ? O1B Cu1B Cu2B 109.79(6) . . ? N4B Cu2B O2B 100.27(11) . . ? N4B Cu2B O3B 170.84(11) . . ? O2B Cu2B O3B 80.59(9) . . ? N4B Cu2B N8B 93.46(11) . . ? O2B Cu2B N8B 164.44(10) . . ? O3B Cu2B N8B 84.70(9) . . ? N4B Cu2B O4B 94.63(10) . . ? O2B Cu2B O4B 104.78(8) . . ? O3B Cu2B O4B 93.96(8) . . ? N8B Cu2B O4B 81.18(8) . . ? N4B Cu2B Cu1B 136.41(8) . . ? O2B Cu2B Cu1B 41.86(7) . . ? O3B Cu2B Cu1B 41.15(6) . . ? N8B Cu2B Cu1B 122.59(7) . . ? O4B Cu2B Cu1B 113.00(5) . . ? C1B O1B Cu1B 106.55(16) . . ? C1B O1B H1P 109.5 . . ? Cu1B O1B H1P 134.2 . . ? C3B O2B Cu2B 127.29(18) . . ? C3B O2B Cu1B 108.19(17) . . ? Cu2B O2B Cu1B 96.98(9) . . ? C9B O3B Cu1B 124.74(18) . . ? C9B O3B Cu2B 109.12(17) . . ? Cu1B O3B Cu2B 97.34(10) . . ? C11B O4B Cu2B 106.56(16) . . ? C11B O4B H4P 109.0 . . ? Cu2B O4B H4P 133.1 . . ? N2B N1B Cu1B 126.4(2) . . ? N3B N2B N1B 176.2(3) . . yes N5B N4B Cu2B 126.5(2) . . ? N6B N5B N4B 176.6(3) . . yes C2B N7B C5B 107.1(2) . . ? C2B N7B C4B 111.2(2) . . ? C5B N7B C4B 111.6(2) . . ? C2B N7B Cu1B 104.71(18) . . ? C5B N7B Cu1B 114.88(19) . . ? C4B N7B Cu1B 107.21(18) . . ? C13B N8B C12B 107.3(2) . . ? C13B N8B C10B 111.8(2) . . ? C12B N8B C10B 110.9(2) . . ? C13B N8B Cu2B 113.25(19) . . ? C12B N8B Cu2B 105.92(17) . . ? C10B N8B Cu2B 107.55(18) . . ? O1B C1B C2B 107.7(2) . . ? O1B C1B H1B1 110.2 . . ? C2B C1B H1B1 110.2 . . ? O1B C1B H1B2 110.2 . . ? C2B C1B H1B2 110.2 . . ? H1B1 C1B H1B2 108.5 . . ? N7B C2B C1B 113.3(2) . . ? N7B C2B H2B1 108.9 . . ? C1B C2B H2B1 108.9 . . ? N7B C2B H2B2 108.9 . . ? C1B C2B H2B2 108.9 . . ? H2B1 C2B H2B2 107.7 . . ? O2B C3B C4B 107.3(2) . . ? O2B C3B H3B1 110.3 . . ? C4B C3B H3B1 110.3 . . ? O2B C3B H3B2 110.3 . . ? C4B C3B H3B2 110.3 . . ? H3B1 C3B H3B2 108.5 . . ? N7B C4B C3B 110.6(2) . . ? N7B C4B H4B1 109.5 . . ? C3B C4B H4B1 109.5 . . ? N7B C4B H4B2 109.5 . . ? C3B C4B H4B2 109.5 . . ? H4B1 C4B H4B2 108.1 . . ? N7B C5B C6B 114.8(2) . . ? N7B C5B H5B1 108.6 . . ? C6B C5B H5B1 108.6 . . ? N7B C5B H5B2 108.6 . . ? C6B C5B H5B2 108.6 . . ? H5B1 C5B H5B2 107.5 . . ? C5B C6B C7B 110.1(3) . . ? C5B C6B H6B1 109.6 . . ? C7B C6B H6B1 109.6 . . ? C5B C6B H6B2 109.6 . . ? C7B C6B H6B2 109.6 . . ? H6B1 C6B H6B2 108.1 . . ? C8B C7B C6B 112.5(3) . . ? C8B C7B H7B1 109.1 . . ? C6B C7B H7B1 109.1 . . ? C8B C7B H7B2 109.1 . . ? C6B C7B H7B2 109.1 . . ? H7B1 C7B H7B2 107.8 . . ? C7B C8B H8B1 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C7B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? O3B C9B C10B 107.2(2) . . ? O3B C9B H9B1 110.3 . . ? C10B C9B H9B1 110.3 . . ? O3B C9B H9B2 110.3 . . ? C10B C9B H9B2 110.3 . . ? H9B1 C9B H9B2 108.5 . . ? N8B C10B C9B 110.4(3) . . ? N8B C10B H10C 109.6 . . ? C9B C10B H10C 109.6 . . ? N8B C10B H10D 109.6 . . ? C9B C10B H10D 109.6 . . ? H10C C10B H10D 108.1 . . ? O4B C11B C12B 107.7(2) . . ? O4B C11B H11C 110.2 . . ? C12B C11B H11C 110.2 . . ? O4B C11B H11D 110.2 . . ? C12B C11B H11D 110.2 . . ? H11C C11B H11D 108.5 . . ? N8B C12B C11B 113.5(2) . . ? N8B C12B H12C 108.9 . . ? C11B C12B H12C 108.9 . . ? N8B C12B H12D 108.9 . . ? C11B C12B H12D 108.9 . . ? H12C C12B H12D 107.7 . . ? N8B C13B C14B 114.4(2) . . ? N8B C13B H13C 108.7 . . ? C14B C13B H13C 108.7 . . ? N8B C13B H13D 108.7 . . ? C14B C13B H13D 108.7 . . ? H13C C13B H13D 107.6 . . ? C15B C14B C13B 111.2(3) . . ? C15B C14B H14C 109.4 . . ? C13B C14B H14C 109.4 . . ? C15B C14B H14D 109.4 . . ? C13B C14B H14D 109.4 . . ? H14C C14B H14D 108.0 . . ? C14B C15B C16B 111.9(3) . . ? C14B C15B H15C 109.2 . . ? C16B C15B H15C 109.2 . . ? C14B C15B H15D 109.2 . . ? C16B C15B H15D 109.2 . . ? H15C C15B H15D 107.9 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 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 _geom_hbond_publ_flag O1B H1P O2 0.86 1.81 2.661(3) 169.3 . yes O4B H4P O3 0.86 1.86 2.711(3) 172.1 . yes O4 H4O O2B 0.83 1.92 2.700(3) 157.3 . yes O1 H1O O3B 0.86 1.92 2.764(3) 165.0 . yes _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.392 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.082 #===END======================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 696846' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C32 H50 Cu2 N2 O8, 2(H2 O)' _chemical_formula_sum 'C32 H54 Cu2 N2 O10' _chemical_formula_weight 753.85 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.7911(11) _cell_length_b 7.2917(3) _cell_length_c 15.5828(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.017(2) _cell_angle_gamma 90.00 _cell_volume 3607.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12719 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 1.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7545 _exptl_absorpt_correction_T_max 0.9208 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The Cu atom is located coordinated by four O atoms and a N atom in a distorted square based pyramidal geometry. The idealized positions of the H~2~O and OH hydrogens were estimated with HYDROGEN (Nardelli, 1999)program and constrained to ride on their parent atom with U~iso~ = 1.5 (parent atom). Other hydrogens were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.42 \%A from atom O5 and the deepest hole is located 0.88 \%A from atom Cu1. ; _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 23323 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4037 _reflns_number_gt 3197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _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, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0517P)^2^+5.1006P] 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 4037 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.003 _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 0.795838(8) 0.20983(4) 0.548921(18) 0.01751(11) Uani 1 1 d . . . O1 O 0.79437(5) -0.1048(2) 0.59952(11) 0.0244(4) Uani 1 1 d . . . H1O H 0.8053 -0.1723 0.5685 0.037 Uiso 1 1 d R . . O2 O 0.75325(5) 0.1993(3) 0.43043(11) 0.0240(4) Uani 1 1 d . . . O3 O 0.84437(5) 0.1378(2) 0.51989(11) 0.0225(4) Uani 1 1 d . . . O4 O 0.84440(6) 0.3892(3) 0.43625(12) 0.0311(4) Uani 1 1 d . . . O5 O 0.70867(8) -0.1673(3) 0.5512(2) 0.0688(9) Uani 1 1 d . . . H5O H 0.7349 -0.1455 0.5742 0.103 Uiso 1 1 d R . . H5P H 0.6925 -0.0700 0.5527 0.103 Uiso 1 1 d R . . N1 N 0.82273(6) 0.2550(3) 0.68638(13) 0.0182(4) Uani 1 1 d . . . C1 C 0.82364(8) -0.0872(3) 0.69067(17) 0.0256(5) Uani 1 1 d . . . H1A H 0.8528 -0.0849 0.6897 0.031 Uiso 1 1 calc R . . H1B H 0.8210 -0.1936 0.7278 0.031 Uiso 1 1 calc R . . C2 C 0.81477(8) 0.0872(3) 0.73232(16) 0.0229(5) Uani 1 1 d . . . H2A H 0.7850 0.0869 0.7290 0.028 Uiso 1 1 calc R . . H2B H 0.8326 0.0909 0.7976 0.028 Uiso 1 1 calc R . . C3 C 0.79832(8) 0.4130(3) 0.70323(16) 0.0239(5) Uani 1 1 d . . . H3A H 0.8072 0.5275 0.6810 0.029 Uiso 1 1 calc R . . H3B H 0.8040 0.4260 0.7696 0.029 Uiso 1 1 calc R . . C4 C 0.74876(8) 0.1180(4) 0.34621(15) 0.0230(5) Uani 1 1 d . . . H4A H 0.7641 -0.0002 0.3556 0.028 Uiso 1 1 calc R . . H4B H 0.7603 0.1994 0.3098 0.028 Uiso 1 1 calc R . . C5 C 0.86859(7) 0.2948(3) 0.72066(16) 0.0224(5) Uani 1 1 d . . . H5A H 0.8838 0.1842 0.7122 0.027 Uiso 1 1 calc R . . H5B H 0.8775 0.3197 0.7870 0.027 Uiso 1 1 calc R . . C6 C 0.88149(8) 0.4563(3) 0.67429(17) 0.0239(5) Uani 1 1 d . . . H6A H 0.8768 0.5720 0.7026 0.029 Uiso 1 1 calc R . . H6B H 0.8637 0.4589 0.6089 0.029 Uiso 1 1 calc R . . C7 C 0.92778(9) 0.4427(4) 0.6828(2) 0.0367(7) Uani 1 1 d . . . H7A H 0.9455 0.4484 0.7482 0.044 Uiso 1 1 calc R . . H7B H 0.9328 0.3228 0.6585 0.044 Uiso 1 1 calc R . . C8 C 0.94066(11) 0.5957(5) 0.6315(3) 0.0526(9) Uani 1 1 d . . . H8A H 0.9233 0.5900 0.5666 0.079 Uiso 1 1 calc R . . H8B H 0.9704 0.5812 0.6380 0.079 Uiso 1 1 calc R . . H8C H 0.9366 0.7145 0.6566 0.079 Uiso 1 1 calc R . . C9 C 0.85756(7) 0.2344(4) 0.46655(16) 0.0223(5) Uani 1 1 d . . . C10 C 0.89273(7) 0.1493(4) 0.44116(15) 0.0209(5) Uani 1 1 d . . . C11 C 0.91405(9) 0.2522(4) 0.39572(18) 0.0281(6) Uani 1 1 d . . . H11 H 0.9065 0.3767 0.3808 0.034 Uiso 1 1 calc R . . C12 C 0.94634(9) 0.1741(4) 0.37208(18) 0.0325(6) Uani 1 1 d . . . H12 H 0.9608 0.2463 0.3416 0.039 Uiso 1 1 calc R . . C13 C 0.95780(7) -0.0081(4) 0.39229(16) 0.0265(6) Uani 1 1 d . . . C14 C 0.99286(9) -0.0942(5) 0.3663(2) 0.0379(7) Uani 1 1 d . . . H14A H 1.0080 -0.1835 0.4131 0.057 Uiso 1 1 calc R . . H14B H 1.0124 0.0014 0.3618 0.057 Uiso 1 1 calc R . . H14C H 0.9809 -0.1564 0.3073 0.057 Uiso 1 1 calc R . . C15 C 0.93633(8) -0.1095(4) 0.43768(17) 0.0265(6) Uani 1 1 d . . . H15 H 0.9438 -0.2342 0.4523 0.032 Uiso 1 1 calc R . . C16 C 0.90424(8) -0.0325(4) 0.46209(16) 0.0237(5) Uani 1 1 d . . . H16 H 0.8900 -0.1044 0.4933 0.028 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 0.01525(15) 0.02169(18) 0.01613(16) -0.00027(12) 0.00606(11) 0.00304(12) O1 0.0257(9) 0.0215(9) 0.0258(9) -0.0051(7) 0.0084(7) -0.0001(7) O2 0.0191(8) 0.0376(11) 0.0155(8) -0.0048(7) 0.0062(6) 0.0073(7) O3 0.0199(8) 0.0276(9) 0.0224(8) 0.0021(7) 0.0103(7) 0.0038(7) O4 0.0316(10) 0.0305(11) 0.0339(10) 0.0084(8) 0.0149(8) 0.0104(8) O5 0.0468(14) 0.0371(13) 0.144(3) -0.0332(16) 0.0600(17) -0.0095(11) N1 0.0200(10) 0.0164(10) 0.0175(9) 0.0006(8) 0.0057(8) -0.0014(8) C1 0.0270(13) 0.0193(12) 0.0266(13) 0.0037(10) 0.0040(10) -0.0018(10) C2 0.0287(13) 0.0203(12) 0.0184(11) 0.0044(10) 0.0063(10) -0.0046(10) C3 0.0285(13) 0.0205(13) 0.0225(12) -0.0048(10) 0.0082(10) 0.0015(10) C4 0.0258(13) 0.0259(14) 0.0190(11) -0.0046(10) 0.0099(10) 0.0041(10) C5 0.0199(12) 0.0194(12) 0.0222(12) 0.0021(10) -0.0003(9) -0.0011(10) C6 0.0232(12) 0.0208(13) 0.0248(12) 0.0020(10) 0.0043(10) -0.0024(10) C7 0.0258(14) 0.0317(16) 0.0495(17) 0.0081(14) 0.0092(12) -0.0022(12) C8 0.0370(18) 0.050(2) 0.073(2) 0.0187(19) 0.0224(17) -0.0077(15) C9 0.0173(11) 0.0286(14) 0.0190(11) -0.0002(10) 0.0037(9) 0.0030(10) C10 0.0168(11) 0.0299(13) 0.0145(10) -0.0019(10) 0.0032(9) -0.0003(10) C11 0.0269(13) 0.0324(15) 0.0264(13) 0.0026(11) 0.0109(11) 0.0007(11) C12 0.0285(14) 0.0472(18) 0.0267(13) -0.0007(13) 0.0159(11) -0.0069(13) C13 0.0170(12) 0.0432(16) 0.0189(11) -0.0111(11) 0.0057(9) -0.0028(11) C14 0.0256(14) 0.057(2) 0.0347(15) -0.0172(14) 0.0152(12) -0.0019(13) C15 0.0233(13) 0.0301(15) 0.0250(12) -0.0040(11) 0.0069(10) 0.0041(11) C16 0.0218(12) 0.0298(14) 0.0205(11) -0.0002(10) 0.0085(10) -0.0002(10) _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 O2 1.9127(16) 7_656 yes Cu1 O2 1.9150(16) . yes Cu1 O3 1.9179(16) . yes Cu1 N1 2.0469(19) . yes Cu1 O1 2.4318(18) . yes Cu1 Cu1 3.0050(5) 7_656 yes O1 C1 1.432(3) . ? O1 H1O 0.8575 . ? O2 C4 1.400(3) . ? O2 Cu1 1.9128(16) 7_656 ? O3 C9 1.280(3) . ? O4 C9 1.245(3) . ? O5 H5O 0.8506 . ? O5 H5P 0.9014 . ? N1 C5 1.484(3) . ? N1 C2 1.488(3) . ? N1 C3 1.492(3) . ? C1 C2 1.503(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(3) 7_656 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C3 1.528(3) 7_656 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.521(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.527(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.521(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.509(3) . ? C10 C16 1.388(4) . ? C10 C11 1.391(4) . ? C11 C12 1.388(4) . ? C11 H11 0.9500 . ? C12 C13 1.389(4) . ? C12 H12 0.9500 . ? C13 C15 1.387(4) . ? C13 C14 1.513(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 O2 Cu1 O2 76.55(7) 7_656 . yes O2 Cu1 O3 174.44(8) 7_656 . ? O2 Cu1 O3 100.53(7) . . ? O2 Cu1 N1 82.42(7) 7_656 . ? O2 Cu1 N1 158.97(8) . . ? O3 Cu1 N1 100.47(8) . . ? O2 Cu1 O1 99.04(7) 7_656 . ? O2 Cu1 O1 100.53(7) . . yes O3 Cu1 O1 86.11(7) . . yes N1 Cu1 O1 82.16(7) . . yes O2 Cu1 Cu1 38.30(5) 7_656 7_656 ? O2 Cu1 Cu1 38.25(5) . 7_656 ? O3 Cu1 Cu1 138.59(5) . 7_656 ? N1 Cu1 Cu1 120.72(6) . 7_656 ? O1 Cu1 Cu1 102.50(4) . 7_656 ? C1 O1 Cu1 98.81(13) . . ? C1 O1 H1O 109.0 . . ? Cu1 O1 H1O 107.4 . . ? C4 O2 Cu1 118.85(14) . 7_656 ? C4 O2 Cu1 136.49(15) . . ? Cu1 O2 Cu1 103.45(7) 7_656 . ? C9 O3 Cu1 121.21(16) . . ? H5O O5 H5P 113.4 . . ? C5 N1 C2 109.03(18) . . ? C5 N1 C3 110.96(19) . . ? C2 N1 C3 110.39(19) . . ? C5 N1 Cu1 116.29(15) . . ? C2 N1 Cu1 106.41(14) . . ? C3 N1 Cu1 103.55(14) . . ? O1 C1 C2 109.4(2) . . ? O1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? O1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? N1 C2 C1 113.09(19) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N1 C3 C4 109.88(19) . 7_656 ? N1 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 7_656 . ? N1 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 7_656 . ? H3A C3 H3B 108.2 . . ? O2 C4 C3 107.16(19) . 7_656 ? O2 C4 H4A 110.3 . . ? C3 C4 H4A 110.3 7_656 . ? O2 C4 H4B 110.3 . . ? C3 C4 H4B 110.3 7_656 . ? H4A C4 H4B 108.5 . . ? N1 C5 C6 114.45(19) . . ? N1 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? N1 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 111.1(2) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 112.1(2) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? 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 . . ? O4 C9 O3 125.9(2) . . ? O4 C9 C10 119.0(2) . . ? O3 C9 C10 115.1(2) . . ? C16 C10 C11 118.9(2) . . ? C16 C10 C9 120.9(2) . . ? C11 C10 C9 120.2(2) . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C15 C13 C12 118.1(2) . . ? C15 C13 C14 120.6(3) . . ? C12 C13 C14 121.3(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C13 121.3(3) . . ? C16 C15 H15 119.4 . . ? C13 C15 H15 119.4 . . ? C15 C16 C10 120.3(2) . . ? C15 C16 H16 119.8 . . ? C10 C16 H16 119.8 . . ? 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 O5 0.86 2.11 2.850(3) 143.6 7_646 yes O5 H5O O1 0.85 1.93 2.769(3) 167.4 . yes O5 H5P O4 0.90 1.86 2.758(3) 172.4 7_656 yes _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.728 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.086 #===END======================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 696847' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 Cu N O4, H2 O' _chemical_formula_sum 'C12 H22 Cu N O5' _chemical_formula_weight 323.85 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 8.4037(5) _cell_length_b 8.5697(5) _cell_length_c 10.9509(6) _cell_angle_alpha 74.038(4) _cell_angle_beta 84.244(3) _cell_angle_gamma 70.545(3) _cell_volume 714.92(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3058 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 1.543 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7655 _exptl_absorpt_correction_T_max 0.9131 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The Cu atom is coordinated by four O atoms and a N atom in a distorted square pyramidal geometry. The H~2~O and OH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.2-1.5 U~eq~ parent atom). Other hydrogens were positioned geometrically and also constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.92 \%A from atom Cu1 and the deepest hole is located 0.80 \%A from atom Cu1. ; _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 13165 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.36 _reflns_number_total 3209 _reflns_number_gt 2601 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0844P)^2^+0.0000P] 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 3209 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.48704(4) 0.61247(4) 0.86675(3) 0.02278(16) Uani 1 1 d . . . O1 O 0.6358(3) 0.5095(3) 1.0083(2) 0.0303(5) Uani 1 1 d . . . O2 O 0.6110(3) 0.4154(3) 0.7429(2) 0.0315(5) Uani 1 1 d . . . H2O H 0.6873 0.3334 0.7846 0.047 Uiso 1 1 d R . . O3 O 0.3242(3) 0.7321(3) 0.7331(2) 0.0235(4) Uani 1 1 d . . . O4 O 0.1229(3) 0.8997(3) 0.8345(2) 0.0278(5) Uani 1 1 d . . . O5 O 0.8349(3) 0.1512(3) 0.8996(2) 0.0485(7) Uani 1 1 d . . . H5O H 0.8506 0.1486 0.9813 0.073 Uiso 1 1 d R . . H5P H 0.9257 0.0800 0.8851 0.073 Uiso 1 1 d R . . N1 N 0.6768(3) 0.7103(3) 0.7851(2) 0.0244(6) Uani 1 1 d . . . C1 C 0.7934(4) 0.5356(4) 0.9940(3) 0.0270(7) Uani 1 1 d . . . H1A H 0.8792 0.4416 0.9647 0.032 Uiso 1 1 calc R . . H1B H 0.8303 0.5397 1.0758 0.032 Uiso 1 1 calc R . . C2 C 0.7711(4) 0.7057(4) 0.8956(3) 0.0285(7) Uani 1 1 d . . . H2A H 0.7075 0.8015 0.9333 0.034 Uiso 1 1 calc R . . H2B H 0.8828 0.7182 0.8670 0.034 Uiso 1 1 calc R . . C3 C 0.6918(4) 0.5157(4) 0.6503(3) 0.0333(8) Uani 1 1 d . . . H3A H 0.6060 0.6071 0.5922 0.040 Uiso 1 1 calc R . . H3B H 0.7703 0.4427 0.5994 0.040 Uiso 1 1 calc R . . C4 C 0.7886(4) 0.5961(4) 0.7094(3) 0.0308(7) Uani 1 1 d . . . H4A H 0.8773 0.5046 0.7650 0.037 Uiso 1 1 calc R . . H4B H 0.8449 0.6630 0.6415 0.037 Uiso 1 1 calc R . . C5 C 0.6141(4) 0.8878(4) 0.7010(3) 0.0268(7) Uani 1 1 d . . . H5A H 0.5593 0.8839 0.6265 0.032 Uiso 1 1 calc R . . H5B H 0.7123 0.9274 0.6694 0.032 Uiso 1 1 calc R . . C6 C 0.4898(4) 1.0185(4) 0.7635(3) 0.0276(7) Uani 1 1 d . . . H6A H 0.5520 1.0585 0.8141 0.033 Uiso 1 1 calc R . . H6B H 0.4139 0.9645 0.8217 0.033 Uiso 1 1 calc R . . C7 C 0.3857(4) 1.1706(4) 0.6626(3) 0.0313(7) Uani 1 1 d . . . H7A H 0.4627 1.2238 0.6051 0.038 Uiso 1 1 calc R . . H7B H 0.3262 1.1288 0.6112 0.038 Uiso 1 1 calc R . . C8 C 0.2565(5) 1.3057(5) 0.7187(4) 0.0429(9) Uani 1 1 d . . . H8A H 0.1820 1.2531 0.7777 0.064 Uiso 1 1 calc R . . H8B H 0.1894 1.3970 0.6502 0.064 Uiso 1 1 calc R . . H8C H 0.3150 1.3541 0.7642 0.064 Uiso 1 1 calc R . . C9 C 0.1832(4) 0.8485(4) 0.7388(3) 0.0231(6) Uani 1 1 d . . . C10 C 0.0870(4) 0.9274(4) 0.6150(3) 0.0227(6) Uani 1 1 d . . . C11 C 0.1264(4) 0.8439(4) 0.5182(3) 0.0251(6) Uani 1 1 d . . . H11 H 0.2135 0.7367 0.5302 0.030 Uiso 1 1 calc R . . C12 C 0.0407(4) 0.9150(4) 0.4050(3) 0.0253(6) Uani 1 1 d . . . H12 H 0.0689 0.8561 0.3400 0.030 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 0.0211(2) 0.0209(2) 0.0209(2) 0.00102(15) -0.00400(14) -0.00377(15) O1 0.0231(11) 0.0380(13) 0.0243(11) 0.0083(10) -0.0076(9) -0.0139(10) O2 0.0326(12) 0.0215(11) 0.0351(13) -0.0044(10) -0.0068(10) -0.0023(9) O3 0.0217(10) 0.0208(10) 0.0220(10) -0.0005(8) -0.0051(8) -0.0018(8) O4 0.0293(11) 0.0279(12) 0.0216(11) -0.0053(9) -0.0041(9) -0.0030(9) O5 0.0534(16) 0.0378(15) 0.0281(13) -0.0066(11) -0.0098(11) 0.0202(12) N1 0.0254(13) 0.0183(12) 0.0228(13) 0.0011(10) -0.0013(10) -0.0031(10) C1 0.0227(14) 0.0268(16) 0.0262(16) 0.0020(13) -0.0050(12) -0.0066(12) C2 0.0260(15) 0.0256(16) 0.0303(17) 0.0003(13) -0.0077(13) -0.0073(13) C3 0.0421(19) 0.0223(16) 0.0248(16) -0.0025(13) -0.0023(14) 0.0010(14) C4 0.0283(16) 0.0275(17) 0.0262(16) -0.0009(13) 0.0058(13) -0.0021(13) C5 0.0291(16) 0.0206(15) 0.0239(15) 0.0026(12) -0.0023(13) -0.0053(12) C6 0.0314(16) 0.0205(15) 0.0288(16) -0.0016(13) -0.0020(13) -0.0088(13) C7 0.0314(17) 0.0238(16) 0.0327(17) -0.0029(14) -0.0030(14) -0.0040(13) C8 0.043(2) 0.0290(18) 0.051(2) -0.0079(17) -0.0011(18) -0.0055(16) C9 0.0236(14) 0.0193(14) 0.0249(15) -0.0012(12) -0.0031(12) -0.0077(12) C10 0.0208(14) 0.0189(14) 0.0249(15) -0.0014(12) -0.0039(11) -0.0042(11) C11 0.0260(15) 0.0198(15) 0.0241(15) -0.0015(12) -0.0039(12) -0.0025(12) C12 0.0280(15) 0.0214(15) 0.0240(15) -0.0053(12) -0.0035(12) -0.0043(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.909(2) . yes Cu1 O1 1.918(2) 2_667 yes Cu1 O3 1.925(2) . yes Cu1 N1 2.059(3) . yes Cu1 O2 2.362(2) . yes Cu1 Cu1 3.0057(7) 2_667 yes O1 C1 1.402(4) . ? O1 Cu1 1.918(2) 2_667 ? O2 C3 1.414(4) . ? O2 H2O 0.8340 . ? O3 C9 1.279(4) . ? O4 C9 1.242(4) . ? O5 H5O 0.9114 . ? O5 H5P 0.8352 . ? N1 C4 1.485(4) . ? N1 C5 1.494(4) . ? N1 C2 1.496(4) . ? C1 C2 1.522(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.510(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.521(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.522(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.517(4) . ? C10 C11 1.391(4) . ? C10 C12 1.393(4) 2_576 ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C10 1.393(4) 2_576 ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 76.50(10) . 2_667 yes O1 Cu1 O3 174.38(9) . . yes O1 Cu1 O3 102.01(9) 2_667 . ? O1 Cu1 N1 83.31(9) . . yes O1 Cu1 N1 159.78(10) 2_667 . ? O3 Cu1 N1 98.00(9) . . yes O1 Cu1 O2 99.17(9) . . yes O1 Cu1 O2 101.57(10) 2_667 . ? O3 Cu1 O2 86.43(8) . . ? N1 Cu1 O2 82.40(9) . . ? O1 Cu1 Cu1 38.35(6) . 2_667 ? O1 Cu1 Cu1 38.15(6) 2_667 2_667 ? O3 Cu1 Cu1 139.90(6) . 2_667 ? N1 Cu1 Cu1 121.65(7) . 2_667 ? O2 Cu1 Cu1 103.25(6) . 2_667 ? C1 O1 Cu1 117.56(18) . . ? C1 O1 Cu1 138.89(19) . 2_667 ? Cu1 O1 Cu1 103.50(10) . 2_667 yes C3 O2 Cu1 98.60(17) . . ? C3 O2 H2O 106.6 . . ? Cu1 O2 H2O 109.0 . . ? C9 O3 Cu1 126.80(19) . . ? H5O O5 H5P 100.8 . . ? C4 N1 C5 108.8(2) . . ? C4 N1 C2 110.0(2) . . ? C5 N1 C2 111.1(2) . . ? C4 N1 Cu1 109.0(2) . . ? C5 N1 Cu1 113.63(19) . . ? C2 N1 Cu1 104.29(18) . . ? O1 C1 C2 106.5(2) . . ? O1 C1 H1A 110.4 . . ? C2 C1 H1A 110.4 . . ? O1 C1 H1B 110.4 . . ? C2 C1 H1B 110.4 . . ? H1A C1 H1B 108.6 . . ? N1 C2 C1 108.8(3) . . ? N1 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? N1 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O2 C3 C4 112.0(3) . . ? O2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? O2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N1 C4 C3 111.8(3) . . ? N1 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 C6 115.0(3) . . ? N1 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? N1 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C5 C6 C7 110.1(3) . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? C8 C7 C6 113.0(3) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? 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 . . ? O4 C9 O3 125.8(3) . . ? O4 C9 C10 119.6(3) . . ? O3 C9 C10 114.6(2) . . ? C11 C10 C12 118.6(3) . 2_576 ? C11 C10 C9 120.3(3) . . ? C12 C10 C9 121.1(3) 2_576 . ? C12 C11 C10 120.7(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C10 120.7(3) . 2_576 ? C11 C12 H12 119.7 . . ? C10 C12 H12 119.7 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 _geom_hbond_publ_flag O2 H2O O5 0.83 1.87 2.699(3) 171.0 . yes O5 H5O O4 0.91 1.96 2.865(3) 169.0 2_667 yes O5 H5P O4 0.84 2.01 2.834(3) 171.4 1_645 yes _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.36 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.860 _refine_diff_density_min -0.853 _refine_diff_density_rms 0.154