# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ashutosh Ghosh' _publ_contact_author_email 'ghosh 59@yahoo.com' _publ_section_title ; Synthesis, crystal structure and magnetic properties of three unprecedented tri-nuclear and one very rare tetra-nuclear copper(II) Schiff-base complexes supported by mixed azido/phenoxo/nitrato or acetato bridges ; loop_ _publ_author_name C.Biswas M.G.B.Drew E.Ruiz E.Marta C.Diaz 'Ashutosh Ghosh' # Attachment '- 1-4.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 773184' #TrackingRef '- 1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H42 B2 Cu3 F8 N10 O4' _chemical_formula_weight 922.94 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0620(11) _cell_length_b 12.1832(12) _cell_length_c 13.4652(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.918(6) _cell_angle_gamma 90.00 _cell_volume 1792.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10477 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 30.00 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 938 _exptl_absorpt_coefficient_mu 1.854 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.874 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 10477 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.2627 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5115 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; w=1/[\s^2^(Fo^2^)+(0.0520P)^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 5115 _refine_ls_number_parameters 248 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1358 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 0.737 _refine_ls_restrained_S_all 0.738 _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 C12 C 0.0713(4) 0.7383(4) 0.4896(3) 0.0302(11) Uani 1 1 d . . . C13 C 0.1633(4) 0.7248(4) 0.4313(3) 0.0347(11) Uani 1 1 d . . . H13 H 0.1637 0.6621 0.3919 0.042 Uiso 1 1 calc R . . C14 C 0.2543(4) 0.8022(4) 0.4303(3) 0.0376(12) Uani 1 1 d . . . H14 H 0.3152 0.7922 0.3907 0.045 Uiso 1 1 calc R . . C15 C 0.2531(4) 0.8954(4) 0.4897(4) 0.0427(13) Uani 1 1 d . . . H15 H 0.3154 0.9471 0.4918 0.051 Uiso 1 1 calc R . . C17 C 0.0673(4) 0.8354(4) 0.5467(3) 0.0312(11) Uani 1 1 d . . . C18 C -0.0312(4) 0.8620(4) 0.6039(3) 0.0350(12) Uani 1 1 d . . . C20 C -0.2367(4) 0.8467(4) 0.6413(3) 0.0382(12) Uani 1 1 d . . . H20A H -0.2393 0.9258 0.6486 0.046 Uiso 1 1 calc R . . H20B H -0.2223 0.8140 0.7078 0.046 Uiso 1 1 calc R . . C21 C -0.3558(4) 0.8057(4) 0.5837(3) 0.0362(11) Uani 1 1 d . . . H21A H -0.4201 0.8131 0.6247 0.043 Uiso 1 1 calc R . . H21B H -0.3780 0.8494 0.5234 0.043 Uiso 1 1 calc R . . C32 C -0.1653(5) 0.7018(4) 0.2748(4) 0.0549(15) Uani 1 1 d D . . H32A H -0.0876 0.7386 0.2850 0.082 Uiso 1 1 calc R . . H32B H -0.2087 0.7199 0.2095 0.082 Uiso 1 1 calc R . . H32C H -0.1525 0.6239 0.2793 0.082 Uiso 1 1 calc R . . N5 N -0.2522(3) 0.4692(3) 0.4185(3) 0.0311(9) Uani 1 1 d . . . N6 N -0.3224(3) 0.4206(3) 0.3662(3) 0.0489(12) Uani 1 1 d . . . C121 C -0.4488(4) 0.6586(4) 0.4787(3) 0.0380(12) Uani 1 1 d . . . H12A H -0.5236 0.6740 0.5038 0.057 Uiso 1 1 calc R . . H12B H -0.4451 0.5818 0.4634 0.057 Uiso 1 1 calc R . . H12C H -0.4460 0.7008 0.4188 0.057 Uiso 1 1 calc R . . C122 C -0.3420(4) 0.6182(4) 0.6435(4) 0.0419(13) Uani 1 1 d . . . H12D H -0.2755 0.6392 0.6945 0.063 Uiso 1 1 calc R . . H12E H -0.3319 0.5431 0.6248 0.063 Uiso 1 1 calc R . . H12F H -0.4179 0.6261 0.6691 0.063 Uiso 1 1 calc R . . C16 C 0.1620(4) 0.9116(4) 0.5444(4) 0.0383(12) Uani 1 1 d . . . H16 H 0.1621 0.9756 0.5821 0.046 Uiso 1 1 calc R . . C171 C -0.0063(4) 0.9450(4) 0.6880(3) 0.0464(13) Uani 1 1 d . . . H17A H -0.0308 1.0166 0.6627 0.070 Uiso 1 1 calc R . . H17B H 0.0796 0.9455 0.7140 0.070 Uiso 1 1 calc R . . H17C H -0.0518 0.9257 0.7406 0.070 Uiso 1 1 calc R . . O11 O -0.0110(2) 0.6598(2) 0.4923(2) 0.0323(7) Uani 1 1 d . . . O31 O -0.2344(3) 0.7355(3) 0.3490(2) 0.0518(10) Uani 1 1 d D . . H31 H -0.279(3) 0.795(3) 0.3456(16) 0.062 Uiso 1 1 d D . . N4 N -0.1801(3) 0.5202(3) 0.4756(3) 0.0340(10) Uani 1 1 d . . . N19 N -0.1384(3) 0.8154(3) 0.5844(3) 0.0327(9) Uani 1 1 d . . . N22 N -0.3432(3) 0.6884(3) 0.5558(3) 0.0331(9) Uani 1 1 d . . . Cu1 Cu -0.17914(4) 0.68197(4) 0.50851(4) 0.03099(17) Uani 1 1 d D . . Cu2 Cu 0.0000 0.5000 0.5000 0.0311(2) Uani 1 2 d S . . B7 B -0.0081(5) 0.4230(5) 0.2255(5) 0.0379(14) Uani 1 1 d . . . F71 F 0.0371(3) 0.4768(3) 0.1513(3) 0.0845(11) Uani 1 1 d . . . F72 F 0.0343(2) 0.3162(2) 0.2308(2) 0.0523(8) Uani 1 1 d . . . F73 F -0.1343(3) 0.4232(2) 0.1998(3) 0.0782(11) Uani 1 1 d . . . F74 F 0.0246(3) 0.4754(3) 0.3129(2) 0.0862(12) 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 C12 0.025(2) 0.028(3) 0.036(3) 0.004(2) -0.002(2) 0.0035(19) C13 0.032(3) 0.041(3) 0.032(3) 0.002(2) 0.006(2) 0.004(2) C14 0.028(2) 0.050(4) 0.036(3) 0.013(3) 0.007(2) 0.002(2) C15 0.031(3) 0.046(4) 0.049(3) 0.017(3) -0.001(2) -0.007(2) C17 0.038(3) 0.029(3) 0.026(3) 0.006(2) 0.0033(19) -0.002(2) C18 0.045(3) 0.030(3) 0.028(3) 0.005(2) 0.001(2) 0.005(2) C20 0.055(3) 0.036(3) 0.027(3) 0.003(2) 0.014(2) 0.008(2) C21 0.037(3) 0.041(3) 0.034(3) 0.004(2) 0.014(2) 0.007(2) C32 0.072(4) 0.055(4) 0.036(3) -0.006(3) 0.003(3) 0.004(3) N5 0.025(2) 0.035(2) 0.034(2) 0.0019(19) 0.0077(17) 0.0019(17) N6 0.040(3) 0.049(3) 0.053(3) -0.005(2) -0.007(2) -0.003(2) C121 0.028(2) 0.049(3) 0.035(3) 0.004(2) -0.001(2) 0.003(2) C122 0.045(3) 0.041(3) 0.042(3) 0.010(3) 0.013(2) 0.002(2) C16 0.044(3) 0.030(3) 0.040(3) 0.003(2) 0.005(2) -0.006(2) C171 0.060(3) 0.041(3) 0.035(3) -0.014(3) -0.003(2) 0.006(2) O11 0.0266(16) 0.0305(19) 0.0409(19) -0.0033(15) 0.0091(13) 0.0002(13) O31 0.060(2) 0.057(3) 0.039(2) 0.0082(18) 0.0124(18) 0.0252(18) N4 0.0238(19) 0.032(2) 0.043(2) -0.0005(18) -0.0039(17) -0.0006(16) N19 0.035(2) 0.032(2) 0.032(2) 0.0024(19) 0.0078(16) 0.0001(18) N22 0.030(2) 0.032(2) 0.039(2) 0.0060(19) 0.0101(16) 0.0016(16) Cu1 0.0274(3) 0.0307(3) 0.0353(3) 0.0005(3) 0.0064(2) 0.0015(2) Cu2 0.0258(4) 0.0289(5) 0.0375(5) -0.0030(4) 0.0013(3) 0.0012(3) B7 0.043(3) 0.026(3) 0.047(4) -0.002(3) 0.012(3) -0.010(3) F71 0.114(3) 0.059(2) 0.096(3) 0.020(2) 0.063(2) 0.0025(19) F72 0.0642(18) 0.0427(19) 0.0488(19) 0.0020(14) 0.0045(14) 0.0106(14) F73 0.0416(18) 0.050(2) 0.137(3) -0.007(2) -0.0061(18) -0.0049(14) F74 0.119(3) 0.081(3) 0.047(2) -0.0291(19) -0.0230(19) 0.027(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 C12 O11 1.325(5) . ? C12 C13 1.387(6) . ? C12 C17 1.416(6) . ? C13 C14 1.381(6) . ? C13 H13 0.9300 . ? C14 C15 1.390(6) . ? C14 H14 0.9300 . ? C15 C16 1.352(6) . ? C15 H15 0.9300 . ? C17 C16 1.404(6) . ? C17 C18 1.464(6) . ? C18 N19 1.304(5) . ? C18 C171 1.511(6) . ? C20 N19 1.475(5) . ? C20 C21 1.506(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N22 1.490(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C32 O31 1.410(6) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? N5 N6 1.131(5) . ? N5 N4 1.193(5) . ? C121 N22 1.483(5) . ? C121 H12A 0.9600 . ? C121 H12B 0.9600 . ? C121 H12C 0.9600 . ? C122 N22 1.456(5) . ? C122 H12D 0.9600 . ? C122 H12E 0.9600 . ? C122 H12F 0.9600 . ? C16 H16 0.9300 . ? C171 H17A 0.9600 . ? C171 H17B 0.9600 . ? C171 H17C 0.9600 . ? O11 Cu1 1.925(3) . ? O11 Cu2 1.952(3) . ? O31 Cu1 2.237(3) . ? O31 H31 0.880(14) . ? N4 Cu2 1.983(3) . ? N4 Cu1 2.020(4) . ? N19 Cu1 1.936(4) . ? N22 Cu1 2.016(3) . ? Cu1 Cu2 2.9876(6) . ? Cu2 O11 1.952(3) 3_566 ? Cu2 N4 1.983(3) 3_566 ? Cu2 Cu1 2.9875(6) 3_566 ? B7 F74 1.338(6) . ? B7 F71 1.354(6) . ? B7 F73 1.385(6) . ? B7 F72 1.382(6) . ? 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 O11 C12 C13 119.9(4) . . ? O11 C12 C17 120.5(4) . . ? C13 C12 C17 119.6(4) . . ? C14 C13 C12 121.6(5) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 118.7(4) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C16 C17 C12 117.0(4) . . ? C16 C17 C18 118.9(4) . . ? C12 C17 C18 124.0(4) . . ? N19 C18 C17 121.7(4) . . ? N19 C18 C171 119.8(4) . . ? C17 C18 C171 118.6(4) . . ? N19 C20 C21 107.7(4) . . ? N19 C20 H20A 110.2 . . ? C21 C20 H20A 110.2 . . ? N19 C20 H20B 110.2 . . ? C21 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? N22 C21 C20 109.9(3) . . ? N22 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? N22 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? O31 C32 H32A 109.5 . . ? O31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N6 N5 N4 178.2(5) . . ? N22 C121 H12A 109.5 . . ? N22 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? N22 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 109.5 . . ? N22 C122 H12D 109.5 . . ? N22 C122 H12E 109.5 . . ? H12D C122 H12E 109.5 . . ? N22 C122 H12F 109.5 . . ? H12D C122 H12F 109.5 . . ? H12E C122 H12F 109.5 . . ? C15 C16 C17 122.5(5) . . ? C15 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C18 C171 H17A 109.5 . . ? C18 C171 H17B 109.5 . . ? H17A C171 H17B 109.5 . . ? C18 C171 H17C 109.5 . . ? H17A C171 H17C 109.5 . . ? H17B C171 H17C 109.5 . . ? C12 O11 Cu1 125.6(3) . . ? C12 O11 Cu2 133.1(3) . . ? Cu1 O11 Cu2 100.78(13) . . ? C32 O31 Cu1 119.9(3) . . ? C32 O31 H31 124.6(16) . . ? Cu1 O31 H31 111.1(14) . . ? N5 N4 Cu2 126.6(3) . . ? N5 N4 Cu1 129.0(3) . . ? Cu2 N4 Cu1 96.53(14) . . ? C18 N19 C20 120.3(4) . . ? C18 N19 Cu1 127.0(3) . . ? C20 N19 Cu1 111.2(3) . . ? C122 N22 C121 109.4(3) . . ? C122 N22 C21 110.4(4) . . ? C121 N22 C21 108.5(3) . . ? C122 N22 Cu1 109.8(3) . . ? C121 N22 Cu1 114.7(3) . . ? C21 N22 Cu1 103.9(2) . . ? O11 Cu1 N19 91.57(13) . . ? O11 Cu1 N22 166.94(13) . . ? N19 Cu1 N22 87.04(15) . . ? O11 Cu1 N4 79.08(13) . . ? N19 Cu1 N4 158.14(14) . . ? N22 Cu1 N4 97.62(15) . . ? O11 Cu1 O31 93.27(12) . . ? N19 Cu1 O31 105.58(14) . . ? N22 Cu1 O31 99.62(13) . . ? N4 Cu1 O31 94.73(14) . . ? O11 Cu1 Cu2 39.94(8) . . ? N19 Cu1 Cu2 122.81(10) . . ? N22 Cu1 Cu2 132.51(11) . . ? N4 Cu1 Cu2 41.27(9) . . ? O31 Cu1 Cu2 105.27(9) . . ? O11 Cu2 O11 179.999(11) . 3_566 ? O11 Cu2 N4 100.65(13) . 3_566 ? O11 Cu2 N4 79.35(13) 3_566 3_566 ? O11 Cu2 N4 79.35(13) . . ? O11 Cu2 N4 100.65(13) 3_566 . ? N4 Cu2 N4 180.00(4) 3_566 . ? O11 Cu2 Cu1 140.72(8) . 3_566 ? O11 Cu2 Cu1 39.28(8) 3_566 3_566 ? N4 Cu2 Cu1 42.21(10) 3_566 3_566 ? N4 Cu2 Cu1 137.79(10) . 3_566 ? O11 Cu2 Cu1 39.28(8) . . ? O11 Cu2 Cu1 140.72(8) 3_566 . ? N4 Cu2 Cu1 137.80(10) 3_566 . ? N4 Cu2 Cu1 42.21(10) . . ? Cu1 Cu2 Cu1 179.999(1) 3_566 . ? F74 B7 F71 109.7(5) . . ? F74 B7 F73 110.1(5) . . ? F71 B7 F73 106.8(5) . . ? F74 B7 F72 111.1(5) . . ? F71 B7 F72 109.4(5) . . ? F73 B7 F72 109.6(4) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.851 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.114 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 773185' #TrackingRef '- 1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H34 Cu3 N12 O8 ' _chemical_formula_weight 809.26 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 10.538(3) _cell_length_b 18.379(5) _cell_length_c 8.705(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.53(4) _cell_angle_gamma 90.00 _cell_volume 1557.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9641 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 826 _exptl_absorpt_coefficient_mu 2.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 9641 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.1300 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4442 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0705P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4442 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1557 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _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 C14 C 0.2023(7) 0.2947(3) 0.9707(7) 0.0487(15) Uani 1 1 d . . . H14 H 0.2187 0.2537 0.9187 0.058 Uiso 1 1 calc R . . C20 C 0.1675(6) 0.5985(3) 1.3511(7) 0.0450(15) Uani 1 1 d . . . H20A H 0.1899 0.5825 1.4647 0.054 Uiso 1 1 calc R . . H20B H 0.0706 0.6107 1.3032 0.054 Uiso 1 1 calc R . . C21 C 0.2520(6) 0.6643(3) 1.3496(7) 0.0428(14) Uani 1 1 d . . . H21A H 0.2101 0.6894 1.2441 0.051 Uiso 1 1 calc R . . H21B H 0.2542 0.6975 1.4373 0.051 Uiso 1 1 calc R . . C23 C 0.4730(6) 0.6171(4) 1.5462(6) 0.0524(17) Uani 1 1 d . . . H23A H 0.5641 0.6039 1.5567 0.079 Uiso 1 1 calc R . . H23B H 0.4283 0.5755 1.5695 0.079 Uiso 1 1 calc R . . H23C H 0.4780 0.6553 1.6235 0.079 Uiso 1 1 calc R . . C24 C 0.4642(6) 0.7064(3) 1.3418(7) 0.0468(15) Uani 1 1 d . . . H24A H 0.4689 0.7443 1.4196 0.070 Uiso 1 1 calc R . . H24B H 0.4143 0.7235 1.2307 0.070 Uiso 1 1 calc R . . H24C H 0.5555 0.6929 1.3537 0.070 Uiso 1 1 calc R . . O31 O 0.2753(4) 0.6415(2) 0.9902(4) 0.0448(10) Uani 1 1 d . . . O32 O 0.3602(5) 0.5885(3) 0.8301(5) 0.0664(14) Uani 1 1 d . . . O34 O 0.1980(4) 0.6659(2) 0.7299(4) 0.0505(11) Uani 1 1 d . . . N22 N 0.3937(4) 0.6427(2) 1.3746(5) 0.0361(11) Uani 1 1 d . . . N33 N 0.2777(4) 0.6322(3) 0.8489(5) 0.0348(10) Uani 1 1 d . . . C181 C -0.0062(5) 0.4755(3) 1.2520(7) 0.0463(15) Uani 1 1 d . . . H18A H 0.0050 0.4365 1.3294 0.069 Uiso 1 1 calc R . . H18B H -0.0844 0.4659 1.1516 0.069 Uiso 1 1 calc R . . H18C H -0.0202 0.5203 1.3000 0.069 Uiso 1 1 calc R . . C12 C 0.2613(5) 0.4185(3) 1.0672(6) 0.0302(11) Uani 1 1 d . . . C13 C 0.2843(6) 0.3550(3) 0.9948(7) 0.0403(13) Uani 1 1 d . . . H13 H 0.3582 0.3534 0.9614 0.048 Uiso 1 1 calc R . . C15 C 0.0944(7) 0.2957(4) 1.0251(9) 0.0588(18) Uani 1 1 d . . . H15 H 0.0379 0.2553 1.0103 0.071 Uiso 1 1 calc R . . C16 C 0.0728(6) 0.3563(3) 1.0998(7) 0.0465(15) Uani 1 1 d . . . H16 H 0.0005 0.3560 1.1361 0.056 Uiso 1 1 calc R . . C17 C 0.1533(5) 0.4199(3) 1.1260(6) 0.0331(12) Uani 1 1 d . . . C18 C 0.1212(5) 0.4816(3) 1.2125(6) 0.0300(12) Uani 1 1 d . . . O11 O 0.3425(4) 0.4765(2) 1.0782(4) 0.0361(9) Uani 1 1 d . . . Cu1 Cu 0.36345(6) 0.55986(4) 1.21531(7) 0.03033(19) Uani 1 1 d . . . Cu2 Cu 0.5000 0.5000 1.0000 0.0338(2) Uani 1 2 d S . . N4 N 0.5487(4) 0.5604(3) 1.2007(5) 0.0386(11) Uani 1 1 d . . . N5 N 0.6611(5) 0.5672(3) 1.3067(5) 0.0415(12) Uani 1 1 d . . . N6 N 0.7667(6) 0.5761(4) 1.4035(7) 0.082(2) Uani 1 1 d . . . N19 N 0.1966(4) 0.5398(2) 1.2542(5) 0.0311(10) 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 C14 0.063(4) 0.030(3) 0.050(3) -0.012(3) 0.019(3) -0.003(3) C20 0.048(3) 0.050(4) 0.055(3) 0.006(3) 0.039(3) 0.010(3) C21 0.051(4) 0.039(4) 0.047(3) -0.002(3) 0.028(3) 0.008(3) C23 0.063(4) 0.067(5) 0.027(3) -0.005(3) 0.018(3) 0.006(4) C24 0.052(4) 0.040(4) 0.052(3) -0.013(3) 0.023(3) -0.015(3) O31 0.056(2) 0.053(3) 0.0307(19) -0.0011(18) 0.0229(18) 0.007(2) O32 0.072(3) 0.092(4) 0.049(2) 0.018(2) 0.039(2) 0.037(3) O34 0.060(3) 0.054(3) 0.033(2) 0.007(2) 0.0119(19) 0.004(2) N22 0.043(3) 0.043(3) 0.031(2) -0.005(2) 0.024(2) -0.003(2) N33 0.033(2) 0.039(3) 0.036(2) -0.001(2) 0.017(2) -0.009(2) C181 0.037(3) 0.053(4) 0.056(4) -0.007(3) 0.027(3) -0.008(3) C12 0.029(3) 0.031(3) 0.028(2) 0.002(2) 0.009(2) 0.003(2) C13 0.045(3) 0.039(4) 0.039(3) -0.002(3) 0.018(3) -0.001(3) C15 0.047(4) 0.044(4) 0.084(5) -0.004(4) 0.024(4) -0.013(3) C16 0.041(3) 0.040(4) 0.061(4) 0.002(3) 0.023(3) 0.000(3) C17 0.027(3) 0.037(3) 0.032(3) 0.003(2) 0.007(2) -0.002(2) C18 0.030(3) 0.033(3) 0.027(2) 0.003(2) 0.011(2) 0.006(2) O11 0.042(2) 0.034(2) 0.044(2) -0.0121(17) 0.0298(18) -0.0067(17) Cu1 0.0301(3) 0.0375(4) 0.0293(3) -0.0040(3) 0.0180(2) -0.0012(3) Cu2 0.0304(5) 0.0465(6) 0.0320(4) -0.0086(4) 0.0205(4) -0.0038(4) N4 0.030(2) 0.055(3) 0.036(2) -0.013(2) 0.018(2) -0.008(2) N5 0.036(3) 0.054(3) 0.036(2) 0.000(2) 0.015(2) 0.002(2) N6 0.044(3) 0.140(7) 0.048(3) -0.004(4) 0.005(3) 0.001(4) N19 0.035(2) 0.029(3) 0.036(2) -0.004(2) 0.022(2) 0.0032(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 C14 C13 1.372(8) . ? C14 C15 1.389(8) . ? C20 N19 1.473(7) . ? C20 C21 1.505(8) . ? C21 N22 1.479(6) . ? C23 N22 1.481(6) . ? C24 N22 1.472(7) . ? O31 N33 1.252(5) . ? O31 Cu1 2.358(4) . ? O32 N33 1.239(6) . ? O32 Cu2 2.309(4) . ? O34 N33 1.222(5) . ? N22 Cu1 2.001(4) . ? C181 C18 1.512(6) . ? C12 O11 1.348(6) . ? C12 C13 1.391(7) . ? C12 C17 1.416(7) . ? C15 C16 1.352(8) . ? C16 C17 1.410(7) . ? C17 C18 1.471(7) . ? C18 N19 1.298(6) . ? O11 Cu1 1.902(3) . ? O11 Cu2 2.066(3) . ? Cu1 N19 1.949(4) . ? Cu1 N4 2.004(4) . ? Cu1 Cu2 2.9768(10) . ? Cu2 N4 1.966(4) . ? Cu2 N4 1.966(4) 3_667 ? Cu2 O11 2.066(3) 3_667 ? Cu2 O32 2.309(4) 3_667 ? Cu2 Cu1 2.9768(10) 3_667 ? N4 N5 1.197(6) . ? N5 N6 1.121(6) . ? 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 C13 C14 C15 119.2(6) . . ? N19 C20 C21 109.3(4) . . ? N22 C21 C20 110.5(5) . . ? N33 O31 Cu1 125.5(3) . . ? N33 O32 Cu2 132.9(3) . . ? C24 N22 C21 108.3(4) . . ? C24 N22 C23 108.5(5) . . ? C21 N22 C23 112.4(4) . . ? C24 N22 Cu1 115.4(3) . . ? C21 N22 Cu1 102.6(3) . . ? C23 N22 Cu1 109.6(4) . . ? O34 N33 O32 120.4(4) . . ? O34 N33 O31 119.8(5) . . ? O32 N33 O31 119.8(5) . . ? O11 C12 C13 118.6(4) . . ? O11 C12 C17 122.5(5) . . ? C13 C12 C17 118.9(5) . . ? C14 C13 C12 122.5(5) . . ? C16 C15 C14 119.0(6) . . ? C15 C16 C17 124.0(5) . . ? C12 C17 C16 116.4(5) . . ? C12 C17 C18 124.9(5) . . ? C16 C17 C18 118.7(5) . . ? N19 C18 C17 122.8(4) . . ? N19 C18 C181 120.0(4) . . ? C17 C18 C181 117.2(5) . . ? C12 O11 Cu1 126.8(3) . . ? C12 O11 Cu2 135.2(3) . . ? Cu1 O11 Cu2 97.13(15) . . ? O11 Cu1 N19 93.50(16) . . ? O11 Cu1 N22 175.57(17) . . ? N19 Cu1 N22 86.48(17) . . ? O11 Cu1 N4 81.15(16) . . ? N19 Cu1 N4 167.81(19) . . ? N22 Cu1 N4 98.00(18) . . ? O11 Cu1 O31 94.41(15) . . ? N19 Cu1 O31 99.81(15) . . ? N22 Cu1 O31 89.95(16) . . ? N4 Cu1 O31 91.56(17) . . ? O11 Cu1 Cu2 43.54(10) . . ? N19 Cu1 Cu2 136.50(12) . . ? N22 Cu1 Cu2 136.92(12) . . ? N4 Cu1 Cu2 40.94(12) . . ? O31 Cu1 Cu2 80.99(9) . . ? N4 Cu2 N4 179.999(1) . 3_667 ? N4 Cu2 O11 101.90(15) . 3_667 ? N4 Cu2 O11 78.10(15) 3_667 3_667 ? N4 Cu2 O11 78.10(15) . . ? N4 Cu2 O11 101.90(15) 3_667 . ? O11 Cu2 O11 180.00(7) 3_667 . ? N4 Cu2 O32 93.23(18) . . ? N4 Cu2 O32 86.77(18) 3_667 . ? O11 Cu2 O32 92.19(15) 3_667 . ? O11 Cu2 O32 87.81(15) . . ? N4 Cu2 O32 86.77(18) . 3_667 ? N4 Cu2 O32 93.23(18) 3_667 3_667 ? O11 Cu2 O32 87.81(15) 3_667 3_667 ? O11 Cu2 O32 92.19(15) . 3_667 ? O32 Cu2 O32 179.999(1) . 3_667 ? N4 Cu2 Cu1 41.91(12) . . ? N4 Cu2 Cu1 138.09(12) 3_667 . ? O11 Cu2 Cu1 140.67(10) 3_667 . ? O11 Cu2 Cu1 39.34(10) . . ? O32 Cu2 Cu1 78.41(10) . . ? O32 Cu2 Cu1 101.59(10) 3_667 . ? N4 Cu2 Cu1 138.09(12) . 3_667 ? N4 Cu2 Cu1 41.91(12) 3_667 3_667 ? O11 Cu2 Cu1 39.33(10) 3_667 3_667 ? O11 Cu2 Cu1 140.66(10) . 3_667 ? O32 Cu2 Cu1 101.59(10) . 3_667 ? O32 Cu2 Cu1 78.41(10) 3_667 3_667 ? Cu1 Cu2 Cu1 180.0 . 3_667 ? N5 N4 Cu2 126.0(4) . . ? N5 N4 Cu1 130.7(4) . . ? Cu2 N4 Cu1 97.16(19) . . ? N6 N5 N4 177.4(7) . . ? C18 N19 C20 121.6(4) . . ? C18 N19 Cu1 127.1(3) . . ? C20 N19 Cu1 111.1(3) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.776 _refine_diff_density_min -0.787 _refine_diff_density_rms 0.108 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 773186' #TrackingRef '- 1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H42 Cu3 N12 O8 ' _chemical_formula_weight 865.36 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1192(11) _cell_length_b 10.2553(16) _cell_length_c 10.6412(18) _cell_angle_alpha 67.626(15) _cell_angle_beta 71.919(13) _cell_angle_gamma 76.806(12) _cell_volume 867.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5331 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 30.00 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 445 _exptl_absorpt_coefficient_mu 1.888 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 5331 _diffrn_reflns_av_R_equivalents 0.2208 _diffrn_reflns_av_sigmaI/netI 0.1489 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4364 _reflns_number_gt 2887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4364 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1209 _refine_ls_R_factor_gt 0.0968 _refine_ls_wR_factor_ref 0.2646 _refine_ls_wR_factor_gt 0.2548 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _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 C12 C 0.0417(7) 0.1460(6) 0.1963(7) 0.0228(13) Uani 1 1 d . . . C13 C -0.0426(7) 0.2727(6) 0.1285(8) 0.0251(13) Uani 1 1 d . . . H13 H -0.0801 0.2767 0.0550 0.030 Uiso 1 1 calc R . . C14 C -0.0713(8) 0.3922(7) 0.1688(9) 0.0354(17) Uani 1 1 d . . . H14 H -0.1294 0.4746 0.1242 0.043 Uiso 1 1 calc R . . C15 C -0.0130(10) 0.3868(9) 0.2747(11) 0.048(2) Uani 1 1 d . . . H15 H -0.0343 0.4654 0.3039 0.057 Uiso 1 1 calc R . . C16 C 0.0764(8) 0.2675(7) 0.3387(8) 0.0304(15) Uani 1 1 d . . . H16 H 0.1179 0.2682 0.4080 0.036 Uiso 1 1 calc R . . C17 C 0.1069(7) 0.1433(6) 0.3018(8) 0.0255(14) Uani 1 1 d . . . C18 C 0.1971(8) 0.0186(7) 0.3820(8) 0.0278(14) Uani 1 1 d . . . C20 C 0.3259(9) -0.2242(8) 0.4415(9) 0.0375(17) Uani 1 1 d . . . H20A H 0.2703 -0.2475 0.5396 0.045 Uiso 1 1 calc R . . H20B H 0.4286 -0.2038 0.4310 0.045 Uiso 1 1 calc R . . C21 C 0.3376(9) -0.3484(8) 0.3884(9) 0.0377(18) Uani 1 1 d . . . H21A H 0.4171 -0.4229 0.4226 0.045 Uiso 1 1 calc R . . H21B H 0.2394 -0.3875 0.4272 0.045 Uiso 1 1 calc R . . C23 C 0.5390(8) -0.2757(9) 0.1867(10) 0.0407(19) Uani 1 1 d . . . H23A H 0.6051 -0.3624 0.2229 0.049 Uiso 1 1 calc R . . H23B H 0.5491 -0.2071 0.2250 0.049 Uiso 1 1 calc R . . C24 C 0.6007(14) -0.2165(15) 0.0223(15) 0.081(4) Uani 1 1 d . . . H24A H 0.6064 -0.2890 -0.0160 0.122 Uiso 1 1 calc R . . H24B H 0.7023 -0.1889 -0.0013 0.122 Uiso 1 1 calc R . . H24C H 0.5310 -0.1355 -0.0159 0.122 Uiso 1 1 calc R . . C25 C 0.3495(9) -0.4231(7) 0.1946(9) 0.0349(16) Uani 1 1 d . . . H25A H 0.3768 -0.3925 0.0929 0.042 Uiso 1 1 calc R . . H25B H 0.2397 -0.4341 0.2267 0.042 Uiso 1 1 calc R . . C26 C 0.4415(9) -0.5674(8) 0.2493(10) 0.044(2) Uani 1 1 d . . . H26A H 0.5503 -0.5578 0.2206 0.067 Uiso 1 1 calc R . . H26B H 0.4233 -0.6323 0.2120 0.067 Uiso 1 1 calc R . . H26C H 0.4089 -0.6030 0.3499 0.067 Uiso 1 1 calc R . . C181 C 0.2440(10) 0.0253(10) 0.5054(10) 0.046(2) Uani 1 1 d . . . H18A H 0.3040 -0.0627 0.5453 0.070 Uiso 1 1 calc R . . H18B H 0.1523 0.0408 0.5753 0.070 Uiso 1 1 calc R . . H18C H 0.3051 0.1019 0.4730 0.070 Uiso 1 1 calc R . . O11 O 0.0617(5) 0.0333(5) 0.1551(5) 0.0252(10) Uani 1 1 d . . . O32 O -0.1343(6) -0.1869(6) 0.1747(6) 0.0398(13) Uani 1 1 d . . . O31 O 0.0112(6) -0.2744(6) 0.3207(7) 0.0412(13) Uani 1 1 d . . . O34 O -0.2279(7) -0.3156(7) 0.3931(8) 0.0557(17) Uani 1 1 d . . . N4 N 0.2048(6) -0.1188(5) 0.0005(7) 0.0236(12) Uani 1 1 d . . . N5 N 0.3021(8) -0.1007(7) -0.1123(8) 0.0411(17) Uani 1 1 d . . . N6 N 0.3930(11) -0.0843(11) -0.2213(11) 0.070(3) Uani 1 1 d . . . N19 N 0.2387(7) -0.0989(6) 0.3522(7) 0.0284(12) Uani 1 1 d . . . N22 N 0.3742(6) -0.3066(5) 0.2385(7) 0.0278(13) Uani 1 1 d . . . N33 N -0.1180(6) -0.2576(6) 0.2951(7) 0.0271(12) Uani 1 1 d . . . Cu2 Cu 0.0000 0.0000 0.0000 0.0225(3) Uani 1 2 d S . . Cu1 Cu 0.21584(8) -0.13191(7) 0.19025(8) 0.0203(3) 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 C12 0.020(3) 0.024(3) 0.030(4) -0.015(3) -0.008(3) -0.002(2) C13 0.022(3) 0.023(3) 0.033(4) -0.012(3) -0.009(3) -0.001(2) C14 0.030(4) 0.030(3) 0.053(5) -0.022(3) -0.014(3) 0.002(3) C15 0.045(5) 0.043(4) 0.071(7) -0.038(4) -0.020(4) 0.005(3) C16 0.037(4) 0.033(3) 0.026(4) -0.015(3) -0.007(3) -0.008(3) C17 0.023(3) 0.026(3) 0.035(4) -0.015(3) -0.014(3) -0.001(2) C18 0.027(3) 0.032(3) 0.035(4) -0.015(3) -0.014(3) -0.006(2) C20 0.039(4) 0.039(4) 0.043(5) -0.012(3) -0.024(4) -0.003(3) C21 0.038(4) 0.040(4) 0.049(5) -0.023(4) -0.031(4) 0.011(3) C23 0.025(3) 0.054(4) 0.054(6) -0.023(4) -0.023(4) 0.001(3) C24 0.063(7) 0.110(10) 0.092(11) -0.044(8) -0.039(7) -0.006(7) C25 0.033(4) 0.034(3) 0.045(5) -0.020(3) -0.016(3) 0.002(3) C26 0.036(4) 0.042(4) 0.054(6) -0.017(4) -0.012(4) 0.000(3) C181 0.049(5) 0.059(5) 0.054(6) -0.035(5) -0.029(4) 0.003(4) O11 0.029(2) 0.0250(19) 0.031(3) -0.0153(19) -0.019(2) 0.0043(17) O32 0.037(3) 0.050(3) 0.038(4) -0.012(3) -0.019(3) -0.009(2) O31 0.029(3) 0.049(3) 0.057(4) -0.024(3) -0.024(3) 0.002(2) O34 0.043(4) 0.063(4) 0.074(5) -0.029(4) -0.024(4) -0.007(3) N4 0.014(2) 0.026(2) 0.035(3) -0.016(2) -0.012(2) 0.0056(19) N5 0.033(3) 0.052(4) 0.054(5) -0.033(4) -0.025(3) 0.013(3) N6 0.056(5) 0.092(7) 0.060(7) -0.033(5) -0.023(5) 0.016(5) N19 0.030(3) 0.032(3) 0.031(3) -0.013(2) -0.017(2) 0.000(2) N22 0.026(3) 0.026(2) 0.040(4) -0.014(3) -0.021(3) 0.004(2) N33 0.025(3) 0.030(3) 0.037(4) -0.021(3) -0.015(3) 0.003(2) Cu2 0.0195(5) 0.0268(5) 0.0307(7) -0.0169(5) -0.0161(5) 0.0055(4) Cu1 0.0183(4) 0.0228(4) 0.0275(5) -0.0133(3) -0.0144(3) 0.0034(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 C12 O11 1.343(6) . ? C12 C13 1.405(8) . ? C12 C17 1.412(9) . ? C13 C14 1.392(8) . ? C14 C15 1.366(12) . ? C15 C16 1.372(11) . ? C16 C17 1.417(8) . ? C17 C18 1.471(9) . ? C18 N19 1.306(8) . ? C18 C181 1.531(10) . ? C20 N19 1.502(9) . ? C20 C21 1.550(10) . ? C21 N22 1.433(10) . ? C23 N22 1.494(9) . ? C23 C24 1.575(16) . ? C25 N22 1.520(8) . ? C25 C26 1.521(10) . ? O11 Cu1 1.934(4) . ? O11 Cu2 2.062(4) . ? O32 N33 1.246(8) . ? O32 Cu2 2.361(6) . ? O31 N33 1.250(7) . ? O31 Cu1 2.374(6) . ? O34 N33 1.263(9) . ? N4 N5 1.228(10) . ? N4 Cu2 1.984(5) . ? N4 Cu1 2.004(6) . ? N5 N6 1.174(12) . ? N19 Cu1 1.956(6) . ? N22 Cu1 2.034(5) . ? Cu2 N4 1.984(5) 2 ? Cu2 O11 2.062(4) 2 ? Cu2 O32 2.361(6) 2 ? Cu2 Cu1 2.9959(8) 2 ? Cu2 Cu1 2.9960(8) . ? 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 O11 C12 C13 118.6(5) . . ? O11 C12 C17 122.4(5) . . ? C13 C12 C17 119.0(5) . . ? C14 C13 C12 121.5(6) . . ? C15 C14 C13 119.0(7) . . ? C14 C15 C16 121.1(6) . . ? C15 C16 C17 121.5(6) . . ? C12 C17 C16 117.7(6) . . ? C12 C17 C18 125.0(5) . . ? C16 C17 C18 117.2(6) . . ? N19 C18 C17 122.4(6) . . ? N19 C18 C181 118.2(6) . . ? C17 C18 C181 119.4(6) . . ? N19 C20 C21 105.7(5) . . ? N22 C21 C20 113.1(7) . . ? N22 C23 C24 115.2(7) . . ? N22 C25 C26 115.3(6) . . ? C12 O11 Cu1 126.8(4) . . ? C12 O11 Cu2 133.8(4) . . ? Cu1 O11 Cu2 97.08(18) . . ? N33 O32 Cu2 129.7(4) . . ? N33 O31 Cu1 126.9(5) . . ? N5 N4 Cu2 117.3(5) . . ? N5 N4 Cu1 132.5(4) . . ? Cu2 N4 Cu1 97.4(2) . . ? N6 N5 N4 178.6(8) . . ? C18 N19 C20 119.7(6) . . ? C18 N19 Cu1 127.4(5) . . ? C20 N19 Cu1 112.7(4) . . ? C21 N22 C23 106.4(6) . . ? C21 N22 C25 110.3(6) . . ? C23 N22 C25 112.5(6) . . ? C21 N22 Cu1 101.7(4) . . ? C23 N22 Cu1 114.1(4) . . ? C25 N22 Cu1 111.1(4) . . ? O32 N33 O31 119.6(7) . . ? O32 N33 O34 122.1(6) . . ? O31 N33 O34 118.3(6) . . ? N4 Cu2 N4 180.0 2 . ? N4 Cu2 O11 78.34(19) 2 2 ? N4 Cu2 O11 101.66(19) . 2 ? N4 Cu2 O11 101.66(19) 2 . ? N4 Cu2 O11 78.34(19) . . ? O11 Cu2 O11 180.0 2 . ? N4 Cu2 O32 87.4(2) 2 . ? N4 Cu2 O32 92.6(2) . . ? O11 Cu2 O32 91.39(19) 2 . ? O11 Cu2 O32 88.61(19) . . ? N4 Cu2 O32 92.6(2) 2 2 ? N4 Cu2 O32 87.4(2) . 2 ? O11 Cu2 O32 88.61(19) 2 2 ? O11 Cu2 O32 91.39(19) . 2 ? O32 Cu2 O32 180.0 . 2 ? N4 Cu2 Cu1 41.56(17) 2 2 ? N4 Cu2 Cu1 138.44(17) . 2 ? O11 Cu2 Cu1 39.85(11) 2 2 ? O11 Cu2 Cu1 140.15(11) . 2 ? O32 Cu2 Cu1 101.37(12) . 2 ? O32 Cu2 Cu1 78.63(12) 2 2 ? N4 Cu2 Cu1 138.44(17) 2 . ? N4 Cu2 Cu1 41.56(17) . . ? O11 Cu2 Cu1 140.15(11) 2 . ? O11 Cu2 Cu1 39.85(11) . . ? O32 Cu2 Cu1 78.63(12) . . ? O32 Cu2 Cu1 101.37(12) 2 . ? Cu1 Cu2 Cu1 180.0 2 . ? O11 Cu1 N19 91.6(2) . . ? O11 Cu1 N4 80.90(19) . . ? N19 Cu1 N4 166.5(2) . . ? O11 Cu1 N22 176.9(2) . . ? N19 Cu1 N22 85.6(2) . . ? N4 Cu1 N22 102.1(2) . . ? O11 Cu1 O31 88.87(19) . . ? N19 Cu1 O31 94.8(2) . . ? N4 Cu1 O31 96.2(2) . . ? N22 Cu1 O31 89.9(2) . . ? O11 Cu1 Cu2 43.07(12) . . ? N19 Cu1 Cu2 134.21(16) . . ? N4 Cu1 Cu2 41.05(13) . . ? N22 Cu1 Cu2 139.47(15) . . ? O31 Cu1 Cu2 80.85(13) . . ? _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.862 _refine_diff_density_max 2.545 _refine_diff_density_min -2.815 _refine_diff_density_rms 0.315 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 773187' #TrackingRef '- 1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 Cu2 N8 O3' _chemical_formula_weight 461.43 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0042(5) _cell_length_b 9.5167(5) _cell_length_c 18.6682(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.833(6) _cell_angle_gamma 90.00 _cell_volume 1739.57(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8320 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 30.00 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 2.478 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 8320 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0834 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4898 _reflns_number_gt 3172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0381P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4898 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.767 _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 0.72476(3) 0.19219(3) 0.055122(18) 0.01545(8) Uani 1 1 d . . . Cu2 Cu 0.91148(3) 0.44155(3) 0.051675(18) 0.01540(8) Uani 1 1 d . . . N1 N 0.9357(2) 0.2844(2) 0.12186(12) 0.0178(5) Uani 1 1 d . . . O11 O 0.76908(17) 0.29263(17) -0.02674(10) 0.0165(4) Uani 1 1 d . . . O31 O 0.76275(18) 0.53096(17) 0.08740(11) 0.0211(4) Uani 1 1 d . . . N22 N 0.6622(2) 0.0745(2) 0.13408(13) 0.0188(5) Uani 1 1 d . . . C12 C 0.8053(2) 0.2383(3) -0.08501(14) 0.0147(5) Uani 1 1 d . . . O32 O 0.61587(18) 0.34997(18) 0.07738(11) 0.0202(4) Uani 1 1 d . . . N6 N 0.7153(2) 0.6871(3) -0.09681(14) 0.0283(6) Uani 1 1 d . . . N4 N 0.9131(2) 0.5982(2) -0.01980(13) 0.0182(5) Uani 1 1 d . . . N2 N 0.9664(2) 0.3049(2) 0.18763(14) 0.0209(5) Uani 1 1 d . . . N19 N 0.7889(2) 0.0141(2) 0.02458(13) 0.0165(5) Uani 1 1 d . . . C34 C 0.5435(3) 0.5710(3) 0.11194(17) 0.0246(6) Uani 1 1 d . . . H34A H 0.4849 0.6081 0.0689 0.037 Uiso 1 1 calc R . . H34B H 0.5885 0.6470 0.1411 0.037 Uiso 1 1 calc R . . H34C H 0.4901 0.5184 0.1398 0.037 Uiso 1 1 calc R . . C13 C 0.8108(3) 0.3248(3) -0.14537(15) 0.0215(6) Uani 1 1 d . . . H13 H 0.7903 0.4198 -0.1430 0.026 Uiso 1 1 calc R . . N5 N 0.8103(2) 0.6425(2) -0.05995(13) 0.0178(5) Uani 1 1 d . . . C21 C 0.7600(3) -0.0452(3) 0.14664(16) 0.0214(6) Uani 1 1 d . . . H21A H 0.7254 -0.1179 0.1744 0.026 Uiso 1 1 calc R . . H21B H 0.8471 -0.0133 0.1749 0.026 Uiso 1 1 calc R . . N3 N 0.9951(3) 0.3163(3) 0.24994(15) 0.0420(7) Uani 1 1 d . . . C14 C 0.8456(3) 0.2729(3) -0.20792(16) 0.0258(7) Uani 1 1 d . . . H14 H 0.8480 0.3331 -0.2469 0.031 Uiso 1 1 calc R . . C18 C 0.8358(3) -0.0072(3) -0.03308(15) 0.0181(6) Uani 1 1 d . . . H18 H 0.8706 -0.0962 -0.0389 0.022 Uiso 1 1 calc R . . C23 C 0.6630(3) 0.1484(3) 0.20416(16) 0.0281(7) Uani 1 1 d . . . H23A H 0.6354 0.0845 0.2382 0.042 Uiso 1 1 calc R . . H23B H 0.6007 0.2262 0.1956 0.042 Uiso 1 1 calc R . . H23C H 0.7534 0.1823 0.2240 0.042 Uiso 1 1 calc R . . C17 C 0.8400(2) 0.0942(3) -0.09023(15) 0.0166(6) Uani 1 1 d . . . C16 C 0.8749(3) 0.0443(3) -0.15503(16) 0.0232(6) Uani 1 1 d . . . H16 H 0.8971 -0.0501 -0.1583 0.028 Uiso 1 1 calc R . . C33 C 0.6483(3) 0.4767(3) 0.09010(15) 0.0174(6) Uani 1 1 d . . . C20 C 0.7799(3) -0.1048(3) 0.07449(16) 0.0215(6) Uani 1 1 d . . . H20A H 0.8630 -0.1602 0.0818 0.026 Uiso 1 1 calc R . . H20B H 0.7036 -0.1651 0.0536 0.026 Uiso 1 1 calc R . . C15 C 0.8772(3) 0.1312(3) -0.21367(17) 0.0263(7) Uani 1 1 d . . . H15 H 0.8994 0.0962 -0.2563 0.032 Uiso 1 1 calc R . . C24 C 0.5198(3) 0.0259(3) 0.10465(17) 0.0256(7) Uani 1 1 d . . . H24A H 0.4881 -0.0278 0.1414 0.038 Uiso 1 1 calc R . . H24B H 0.5183 -0.0317 0.0623 0.038 Uiso 1 1 calc R . . H24C H 0.4615 0.1058 0.0914 0.038 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 0.01454(15) 0.01232(15) 0.02108(18) -0.00007(14) 0.00737(13) -0.00042(13) Cu2 0.01205(15) 0.01375(15) 0.02202(18) 0.00210(15) 0.00725(13) 0.00031(13) N1 0.0189(11) 0.0159(11) 0.0188(13) 0.0025(10) 0.0047(10) 0.0004(9) O11 0.0180(9) 0.0127(9) 0.0202(10) -0.0007(8) 0.0070(8) -0.0005(7) O31 0.0176(9) 0.0145(9) 0.0345(12) -0.0016(9) 0.0131(9) 0.0014(7) N22 0.0149(11) 0.0175(11) 0.0245(13) -0.0009(10) 0.0051(10) -0.0044(9) C12 0.0079(11) 0.0191(13) 0.0163(14) -0.0023(11) 0.0008(10) 0.0000(10) O32 0.0167(9) 0.0155(9) 0.0306(12) -0.0007(9) 0.0100(9) -0.0006(8) N6 0.0188(12) 0.0269(13) 0.0375(16) -0.0003(13) 0.0021(11) 0.0030(11) N4 0.0137(11) 0.0160(11) 0.0271(14) 0.0034(10) 0.0090(10) 0.0023(9) N2 0.0178(11) 0.0187(12) 0.0271(14) 0.0018(12) 0.0069(10) 0.0017(10) N19 0.0121(10) 0.0123(10) 0.0243(13) 0.0006(10) 0.0021(10) -0.0016(9) C34 0.0171(13) 0.0218(14) 0.0371(18) -0.0054(14) 0.0107(13) 0.0032(12) C13 0.0204(14) 0.0200(14) 0.0243(16) 0.0007(13) 0.0050(12) 0.0028(12) N5 0.0161(12) 0.0133(11) 0.0259(14) -0.0017(10) 0.0091(11) -0.0021(9) C21 0.0176(13) 0.0206(14) 0.0253(16) 0.0072(13) 0.0027(12) -0.0004(12) N3 0.0464(17) 0.0533(18) 0.0249(16) -0.0030(15) 0.0038(14) -0.0035(15) C14 0.0222(14) 0.0354(17) 0.0205(16) 0.0043(14) 0.0061(13) 0.0070(13) C18 0.0127(12) 0.0140(12) 0.0268(16) -0.0037(12) 0.0016(12) -0.0014(10) C23 0.0327(17) 0.0287(16) 0.0256(17) -0.0017(14) 0.0123(14) -0.0041(14) C17 0.0121(12) 0.0168(13) 0.0208(15) -0.0021(11) 0.0034(11) -0.0001(10) C16 0.0174(13) 0.0222(15) 0.0300(17) -0.0079(13) 0.0050(12) 0.0032(12) C33 0.0191(13) 0.0179(13) 0.0166(14) 0.0038(11) 0.0070(11) 0.0041(11) C20 0.0213(14) 0.0148(13) 0.0289(17) 0.0037(12) 0.0063(13) 0.0005(11) C15 0.0211(14) 0.0395(17) 0.0199(16) -0.0064(14) 0.0076(13) 0.0060(13) C24 0.0148(13) 0.0309(16) 0.0307(18) 0.0075(14) 0.0035(12) -0.0013(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 O11 1.9296(17) . ? Cu1 N19 1.939(2) . ? Cu1 O32 1.9492(17) . ? Cu1 N22 2.049(2) . ? Cu1 N1 2.387(2) . ? Cu1 Cu2 3.0289(4) . ? Cu2 O31 1.9468(17) . ? Cu2 N1 1.971(2) . ? Cu2 N4 2.002(2) 3_765 ? Cu2 N4 2.003(2) . ? Cu2 O11 2.3077(17) . ? Cu2 Cu2 3.0820(6) 3_765 ? N1 N2 1.219(3) . ? O11 C12 1.321(3) . ? O31 C33 1.267(3) . ? N22 C23 1.484(3) . ? N22 C21 1.489(3) . ? N22 C24 1.491(3) . ? C12 C13 1.406(4) . ? C12 C17 1.422(3) . ? O32 C33 1.259(3) . ? N6 N5 1.136(3) . ? N4 N5 1.217(3) . ? N4 Cu2 2.002(2) 3_765 ? N2 N3 1.145(3) . ? N19 C18 1.276(3) . ? N19 C20 1.480(3) . ? C34 C33 1.498(3) . ? C13 C14 1.377(4) . ? C21 C20 1.512(4) . ? C14 C15 1.394(4) . ? C18 C17 1.446(4) . ? C17 C16 1.409(4) . ? C16 C15 1.376(4) . ? 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 O11 Cu1 N19 93.24(8) . . ? O11 Cu1 O32 90.94(7) . . ? N19 Cu1 O32 165.73(8) . . ? O11 Cu1 N22 173.89(8) . . ? N19 Cu1 N22 84.39(9) . . ? O32 Cu1 N22 90.06(8) . . ? O11 Cu1 N1 84.79(8) . . ? N19 Cu1 N1 99.45(8) . . ? O32 Cu1 N1 94.51(7) . . ? N22 Cu1 N1 101.15(8) . . ? O11 Cu1 Cu2 49.62(5) . . ? N19 Cu1 Cu2 115.84(6) . . ? O32 Cu1 Cu2 77.00(5) . . ? N22 Cu1 Cu2 136.41(6) . . ? N1 Cu1 Cu2 40.54(5) . . ? O31 Cu2 N1 95.89(8) . . ? O31 Cu2 N4 164.34(8) . 3_765 ? N1 Cu2 N4 93.34(9) . 3_765 ? O31 Cu2 N4 90.80(8) . . ? N1 Cu2 N4 172.42(9) . . ? N4 Cu2 N4 79.36(9) 3_765 . ? O31 Cu2 O11 94.01(7) . . ? N1 Cu2 O11 86.06(8) . . ? N4 Cu2 O11 99.23(8) 3_765 . ? N4 Cu2 O11 97.05(8) . . ? O31 Cu2 Cu1 79.46(5) . . ? N1 Cu2 Cu1 51.94(6) . . ? N4 Cu2 Cu1 116.14(6) 3_765 . ? N4 Cu2 Cu1 133.35(7) . . ? O11 Cu2 Cu1 39.57(4) . . ? O31 Cu2 Cu2 129.38(5) . 3_765 ? N1 Cu2 Cu2 133.00(6) . 3_765 ? N4 Cu2 Cu2 39.70(6) 3_765 3_765 ? N4 Cu2 Cu2 39.67(6) . 3_765 ? O11 Cu2 Cu2 100.59(5) . 3_765 ? Cu1 Cu2 Cu2 137.070(18) . 3_765 ? N2 N1 Cu2 121.29(18) . . ? N2 N1 Cu1 126.70(17) . . ? Cu2 N1 Cu1 87.52(8) . . ? C12 O11 Cu1 127.22(16) . . ? C12 O11 Cu2 121.66(15) . . ? Cu1 O11 Cu2 90.81(7) . . ? C33 O31 Cu2 126.61(17) . . ? C23 N22 C21 109.8(2) . . ? C23 N22 C24 107.7(2) . . ? C21 N22 C24 111.6(2) . . ? C23 N22 Cu1 115.35(17) . . ? C21 N22 Cu1 104.09(15) . . ? C24 N22 Cu1 108.33(17) . . ? O11 C12 C13 119.5(2) . . ? O11 C12 C17 123.1(2) . . ? C13 C12 C17 117.4(2) . . ? C33 O32 Cu1 130.15(17) . . ? N5 N4 Cu2 124.32(18) . 3_765 ? N5 N4 Cu2 123.19(17) . . ? Cu2 N4 Cu2 100.64(9) 3_765 . ? N3 N2 N1 176.2(3) . . ? C18 N19 C20 119.3(2) . . ? C18 N19 Cu1 126.03(19) . . ? C20 N19 Cu1 114.63(17) . . ? C14 C13 C12 121.8(3) . . ? N6 N5 N4 178.3(3) . . ? N22 C21 C20 110.4(2) . . ? C13 C14 C15 120.9(3) . . ? N19 C18 C17 126.0(2) . . ? C16 C17 C12 119.4(3) . . ? C16 C17 C18 117.3(2) . . ? C12 C17 C18 123.3(2) . . ? C15 C16 C17 121.9(3) . . ? O32 C33 O31 125.7(2) . . ? O32 C33 C34 117.2(2) . . ? O31 C33 C34 117.1(2) . . ? N19 C20 C21 108.0(2) . . ? C16 C15 C14 118.6(3) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.452 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.090 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END