Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Dr Jennifer Scott' _publ_contact_author_email Jennifer.Scott@rmc.ca loop_ _publ_author_name D.Reid J.Cull K.Chisholm A.Langlois P.-H.Lin J.Long O.Lebel ; I.Korobkov ; R.Wang J.Wuest M.Murugesu J.Scott data_jen03_complex_2 _database_code_depnum_ccdc_archive 'CCDC 806769' #TrackingRef '- cifs_complexes 2-5_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H54 Co2 N16 O6 S4' _chemical_formula_weight 1053.05 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.8096(18) _cell_length_b 17.481(3) _cell_length_c 14.825(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.962(3) _cell_angle_gamma 90.00 _cell_volume 2523.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1292 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 20.39 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.880 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9329 _exptl_absorpt_correction_T_max 0.9491 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11595 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4956 _reflns_number_gt 2479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^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 4956 _refine_ls_number_parameters 303 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1323 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1353 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.991 _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 Co1 Co 0.64845(7) 0.85856(4) 0.04813(4) 0.0497(2) Uani 1 1 d . . . O1 O 0.8508(3) 0.83573(19) 0.1172(2) 0.0617(10) Uani 1 1 d . . . O2 O 0.5784(4) 0.8585(2) 0.1735(2) 0.0643(11) Uani 1 1 d D B . H2H H 0.532(6) 0.892(3) 0.185(4) 0.077 Uiso 1 1 d D . . N1 N 0.4466(4) 0.9016(2) -0.0085(2) 0.0428(9) Uani 1 1 d . . . N2 N 0.2132(4) 0.8973(2) -0.0760(3) 0.0577(11) Uani 1 1 d . . . N3 N 0.3307(4) 1.0173(2) -0.0540(2) 0.0486(10) Uani 1 1 d . . . N4 N 0.1069(4) 1.0086(3) -0.1216(3) 0.0960(18) Uani 1 1 d . . . H4A H 0.0339 0.9823 -0.1408 0.115 Uiso 1 1 calc R . . H4B H 0.1065 1.0581 -0.1276 0.115 Uiso 1 1 calc R . . N5 N 0.3311(4) 0.7882(2) -0.0281(2) 0.0512(11) Uani 1 1 d . . . H5B H 0.4098 0.7696 -0.0047 0.061 Uiso 1 1 calc R . . N6 N 1.0426(5) 0.7686(2) 0.1622(3) 0.0636(12) Uani 1 1 d . . . N7 N 0.7312(5) 0.8657(3) -0.0725(3) 0.0656(12) Uani 1 1 d . . . N8 N 0.6135(4) 0.7420(2) 0.0359(3) 0.0614(12) Uani 1 1 d . . . S1 S 0.82619(17) 0.91807(11) -0.22997(10) 0.0862(6) Uani 1 1 d . . . S2 S 0.6711(2) 0.59126(9) 0.00321(12) 0.0991(7) Uani 1 1 d . . . C1 C 0.3275(5) 0.8637(3) -0.0380(3) 0.0435(11) Uani 1 1 d . . . C2 C 0.2175(5) 0.9738(3) -0.0837(3) 0.0588(14) Uani 1 1 d . . . C3 C 0.4368(5) 0.9768(3) -0.0177(3) 0.0432(11) Uani 1 1 d . . . C4 C 0.2246(5) 0.7329(3) -0.0503(3) 0.0511(13) Uani 1 1 d . . . C5 C 0.2663(6) 0.6564(3) -0.0513(4) 0.0659(15) Uani 1 1 d . . . H5A H 0.3601 0.6440 -0.0402 0.079 Uiso 1 1 calc R . . C6 C 0.1705(7) 0.5997(3) -0.0683(4) 0.0834(19) Uani 1 1 d . . . H6A H 0.1992 0.5484 -0.0687 0.100 Uiso 1 1 calc R . . C7 C 0.0346(7) 0.6163(3) -0.0846(4) 0.089(2) Uani 1 1 d . . . H7A H -0.0298 0.5767 -0.0971 0.107 Uiso 1 1 calc R . . C8 C -0.0095(6) 0.6918(4) -0.0828(4) 0.0796(18) Uani 1 1 d . . . H8A H -0.1038 0.7033 -0.0921 0.095 Uiso 1 1 calc R . . C9 C 0.0866(5) 0.7502(3) -0.0673(4) 0.0646(15) Uani 1 1 d . . . H9A H 0.0577 0.8015 -0.0683 0.078 Uiso 1 1 calc R . . C10 C 0.9124(6) 0.7746(3) 0.1315(3) 0.0605(14) Uani 1 1 d . . . H10A H 0.8621 0.7292 0.1196 0.073 Uiso 1 1 calc R . . C11 C 1.1289(6) 0.8374(4) 0.1792(5) 0.096(2) Uani 1 1 d . . . H11A H 1.0952 0.8773 0.1368 0.144 Uiso 1 1 calc R . . H11B H 1.2230 0.8250 0.1710 0.144 Uiso 1 1 calc R . . H11C H 1.1252 0.8550 0.2408 0.144 Uiso 1 1 calc R . . C12 C 1.1095(6) 0.6939(3) 0.1770(4) 0.0838(19) Uani 1 1 d . . . H12A H 1.0451 0.6538 0.1558 0.126 Uiso 1 1 calc R . . H12B H 1.1388 0.6869 0.2414 0.126 Uiso 1 1 calc R . . H12C H 1.1887 0.6915 0.1438 0.126 Uiso 1 1 calc R . . C13 C 0.6137(6) 0.8049(3) 0.2486(4) 0.0722(16) Uani 1 1 d D . . H13A H 0.6754 0.7665 0.2275 0.087 Uiso 1 1 calc R A 1 H13B H 0.6672 0.8334 0.2976 0.087 Uiso 1 1 calc R A 1 C14A C 0.506(4) 0.764(3) 0.289(4) 0.079(7) Uani 0.33 1 d PD B 1 H14A H 0.5160 0.7732 0.3537 0.119 Uiso 0.33 1 calc PR B 1 H14B H 0.5150 0.7093 0.2778 0.119 Uiso 0.33 1 calc PR B 1 H14C H 0.4170 0.7813 0.2615 0.119 Uiso 0.33 1 calc PR B 1 C14B C 0.486(3) 0.781(4) 0.282(3) 0.079(7) Uani 0.33 1 d PD B 2 H14D H 0.4640 0.8174 0.3281 0.119 Uiso 0.33 1 calc PR B 2 H14E H 0.4976 0.7308 0.3086 0.119 Uiso 0.33 1 calc PR B 2 H14F H 0.4126 0.7807 0.2323 0.119 Uiso 0.33 1 calc PR B 2 C14C C 0.492(3) 0.757(2) 0.252(3) 0.079(7) Uani 0.33 1 d PD B 3 H14G H 0.4596 0.7386 0.1915 0.119 Uiso 0.33 1 calc PR B 3 H14H H 0.4207 0.7863 0.2756 0.119 Uiso 0.33 1 calc PR B 3 H14I H 0.5163 0.7133 0.2917 0.119 Uiso 0.33 1 calc PR B 3 C15 C 0.7732(5) 0.8865(3) -0.1368(4) 0.0528(13) Uani 1 1 d . . . C16 C 0.6368(5) 0.6783(3) 0.0225(3) 0.0562(14) Uani 1 1 d . . . O3 O 0.4625(6) 0.9863(3) 0.2257(4) 0.1183(19) Uani 1 1 d D . . H3H H 0.389(6) 1.005(4) 0.216(5) 0.142 Uiso 1 1 d D . . C17 C 0.5249(10) 1.0256(8) 0.2997(7) 0.205(7) Uani 1 1 d D . . H17A H 0.5044 0.9997 0.3551 0.246 Uiso 1 1 calc R . . H17B H 0.4851 1.0770 0.2997 0.246 Uiso 1 1 calc R . . C18 C 0.6716(13) 1.0325(6) 0.3027(6) 0.206(6) Uani 1 1 d D . . H18A H 0.7074 1.0629 0.3550 0.309 Uiso 1 1 calc R . . H18B H 0.6934 1.0573 0.2477 0.309 Uiso 1 1 calc R . . H18C H 0.7129 0.9821 0.3073 0.309 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 Co1 0.0462(4) 0.0381(4) 0.0628(5) 0.0027(3) -0.0012(3) 0.0065(3) O1 0.060(2) 0.043(2) 0.079(2) 0.0083(17) -0.0077(18) 0.0124(18) O2 0.078(3) 0.052(2) 0.063(2) 0.0101(19) 0.0112(19) 0.023(2) N1 0.042(2) 0.029(2) 0.056(2) 0.0040(17) 0.0010(18) 0.0028(18) N2 0.049(3) 0.039(3) 0.081(3) 0.007(2) -0.011(2) 0.001(2) N3 0.041(3) 0.039(2) 0.063(3) 0.0045(19) -0.0017(19) 0.0010(19) N4 0.049(3) 0.042(3) 0.184(5) 0.019(3) -0.036(3) -0.004(2) N5 0.043(3) 0.036(2) 0.071(3) 0.0029(19) -0.006(2) 0.0041(19) N6 0.061(3) 0.057(3) 0.069(3) 0.007(2) -0.007(2) 0.014(2) N7 0.062(3) 0.062(3) 0.074(3) 0.001(3) 0.012(3) 0.014(2) N8 0.050(3) 0.045(3) 0.087(3) -0.002(2) -0.004(2) 0.007(2) S1 0.0727(11) 0.1181(15) 0.0680(10) 0.0006(9) 0.0090(8) -0.0091(10) S2 0.1454(18) 0.0451(10) 0.1021(13) -0.0103(9) -0.0042(12) 0.0245(10) C1 0.044(3) 0.032(3) 0.053(3) 0.004(2) 0.001(2) 0.003(2) C2 0.042(3) 0.048(3) 0.083(4) 0.013(3) -0.007(3) 0.004(3) C3 0.041(3) 0.037(3) 0.051(3) 0.000(2) 0.003(2) 0.002(2) C4 0.049(3) 0.042(3) 0.060(3) 0.002(2) -0.004(2) 0.003(2) C5 0.064(4) 0.044(3) 0.086(4) 0.003(3) -0.009(3) 0.005(3) C6 0.080(5) 0.044(4) 0.119(5) 0.003(3) -0.014(4) -0.006(3) C7 0.084(5) 0.047(4) 0.129(6) 0.001(4) -0.015(4) -0.020(4) C8 0.059(4) 0.065(4) 0.110(5) 0.002(3) -0.007(3) -0.015(3) C9 0.052(4) 0.050(3) 0.089(4) 0.005(3) 0.000(3) -0.002(3) C10 0.054(4) 0.049(3) 0.076(4) 0.006(3) -0.002(3) 0.003(3) C11 0.054(4) 0.076(5) 0.150(6) -0.005(4) -0.023(4) 0.008(3) C12 0.072(4) 0.078(4) 0.100(5) 0.016(4) 0.000(3) 0.028(4) C13 0.078(4) 0.070(4) 0.067(4) 0.010(3) 0.003(3) 0.008(3) C14A 0.071(7) 0.100(18) 0.067(14) 0.053(12) 0.012(9) 0.020(7) C14B 0.071(7) 0.100(18) 0.067(14) 0.053(12) 0.012(9) 0.020(7) C14C 0.071(7) 0.100(18) 0.067(14) 0.053(12) 0.012(9) 0.020(7) C15 0.038(3) 0.054(3) 0.065(4) -0.010(3) -0.001(3) 0.009(2) C16 0.059(4) 0.042(3) 0.064(3) 0.002(3) -0.007(3) 0.008(3) O3 0.135(5) 0.108(4) 0.108(4) -0.015(3) 0.001(3) 0.071(4) C17 0.153(10) 0.319(18) 0.131(8) -0.058(10) -0.035(8) 0.125(12) C18 0.315(18) 0.174(11) 0.129(8) -0.009(7) 0.035(11) -0.126(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 Co1 N7 2.056(5) . ? Co1 O2 2.058(4) . ? Co1 N8 2.071(4) . ? Co1 O1 2.158(3) . ? Co1 N3 2.180(4) 3_675 ? Co1 N1 2.188(4) . ? O1 C10 1.233(5) . ? O2 C13 1.464(6) . ? O2 H2H 0.78(4) . ? N1 C3 1.323(5) . ? N1 C1 1.368(5) . ? N2 C1 1.329(5) . ? N2 C2 1.343(6) . ? N3 C3 1.319(5) . ? N3 C2 1.375(6) . ? N3 Co1 2.180(4) 3_675 ? N4 C2 1.310(6) . ? N4 H4A 0.8700 . ? N4 H4B 0.8700 . ? N5 C1 1.328(5) . ? N5 C4 1.433(6) . ? N5 H5B 0.8700 . ? N6 C10 1.307(6) . ? N6 C12 1.466(6) . ? N6 C11 1.475(7) . ? N7 C15 1.142(6) . ? N8 C16 1.159(6) . ? S1 C15 1.630(6) . ? S2 C16 1.592(6) . ? C3 C3 1.521(9) 3_675 ? C4 C9 1.380(7) . ? C4 C5 1.398(6) . ? C5 C6 1.369(7) . ? C5 H5A 0.9400 . ? C6 C7 1.357(8) . ? C6 H6A 0.9400 . ? C7 C8 1.390(8) . ? C7 H7A 0.9400 . ? C8 C9 1.390(7) . ? C8 H8A 0.9400 . ? C9 H9A 0.9400 . ? C10 H10A 0.9400 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 C14B 1.459(15) . ? C13 C14A 1.461(15) . ? C13 C14C 1.465(15) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14A H14A 0.9700 . ? C14A H14B 0.9700 . ? C14A H14C 0.9700 . ? C14B H14D 0.9700 . ? C14B H14E 0.9700 . ? C14B H14F 0.9700 . ? C14C H14G 0.9700 . ? C14C H14H 0.9700 . ? C14C H14I 0.9700 . ? O3 C17 1.374(8) . ? O3 H3H 0.79(5) . ? C17 C18 1.439(8) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Co1 O2 174.90(17) . . ? N7 Co1 N8 93.57(17) . . ? O2 Co1 N8 90.50(16) . . ? N7 Co1 O1 89.22(16) . . ? O2 Co1 O1 87.74(14) . . ? N8 Co1 O1 89.59(15) . . ? N7 Co1 N3 85.93(16) . 3_675 ? O2 Co1 N3 90.26(14) . 3_675 ? N8 Co1 N3 175.29(16) . 3_675 ? O1 Co1 N3 95.09(13) . 3_675 ? N7 Co1 N1 94.57(16) . . ? O2 Co1 N1 87.75(14) . . ? N8 Co1 N1 99.91(15) . . ? O1 Co1 N1 169.51(13) . . ? N3 Co1 N1 75.48(13) 3_675 . ? C10 O1 Co1 130.2(3) . . ? C13 O2 Co1 127.8(3) . . ? C13 O2 H2H 114(4) . . ? Co1 O2 H2H 118(4) . . ? C3 N1 C1 113.5(4) . . ? C3 N1 Co1 115.6(3) . . ? C1 N1 Co1 130.9(3) . . ? C1 N2 C2 116.2(4) . . ? C3 N3 C2 113.6(4) . . ? C3 N3 Co1 116.9(3) . 3_675 ? C2 N3 Co1 129.3(3) . 3_675 ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C1 N5 C4 129.5(4) . . ? C1 N5 H5B 115.2 . . ? C4 N5 H5B 115.2 . . ? C10 N6 C12 121.7(5) . . ? C10 N6 C11 120.7(5) . . ? C12 N6 C11 117.6(5) . . ? C15 N7 Co1 164.9(4) . . ? C16 N8 Co1 157.9(4) . . ? N5 C1 N2 119.7(4) . . ? N5 C1 N1 115.8(4) . . ? N2 C1 N1 124.5(4) . . ? N4 C2 N2 117.8(5) . . ? N4 C2 N3 118.3(5) . . ? N2 C2 N3 123.9(4) . . ? N3 C3 N1 128.3(4) . . ? N3 C3 C3 115.1(5) . 3_675 ? N1 C3 C3 116.6(5) . 3_675 ? C9 C4 C5 119.4(5) . . ? C9 C4 N5 124.4(4) . . ? C5 C4 N5 116.2(4) . . ? C6 C5 C4 119.9(5) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C7 C6 C5 121.0(6) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C6 C7 C8 120.1(6) . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C9 C8 C7 119.6(6) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C4 C9 C8 120.0(5) . . ? C4 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? O1 C10 N6 124.6(5) . . ? O1 C10 H10A 117.7 . . ? N6 C10 H10A 117.7 . . ? N6 C11 H11A 109.5 . . ? N6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N6 C12 H12A 109.5 . . ? N6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14B C13 C14A 15(3) . . ? C14B C13 O2 107.8(16) . . ? C14A C13 O2 121(2) . . ? C14B C13 C14C 25(4) . . ? C14A C13 C14C 22(3) . . ? O2 C13 C14C 106.1(18) . . ? C14B C13 H13A 120.2 . . ? C14A C13 H13A 107.2 . . ? O2 C13 H13A 107.2 . . ? C14C C13 H13A 98.8 . . ? C14B C13 H13B 107.0 . . ? C14A C13 H13B 107.2 . . ? O2 C13 H13B 107.2 . . ? C14C C13 H13B 129.0 . . ? H13A C13 H13B 106.8 . . ? C13 C14A H14A 109.5 . . ? C13 C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? C13 C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? C13 C14B H14D 109.5 . . ? C13 C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13 C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C13 C14C H14G 109.5 . . ? C13 C14C H14H 109.5 . . ? H14G C14C H14H 109.5 . . ? C13 C14C H14I 109.5 . . ? H14G C14C H14I 109.5 . . ? H14H C14C H14I 109.5 . . ? N7 C15 S1 177.3(5) . . ? N8 C16 S2 179.0(5) . . ? C17 O3 H3H 104(6) . . ? O3 C17 C18 114.4(9) . . ? O3 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? O3 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N7 Co1 O1 C10 -88.2(4) . . . . ? O2 Co1 O1 C10 95.9(4) . . . . ? N8 Co1 O1 C10 5.4(4) . . . . ? N3 Co1 O1 C10 -174.0(4) 3_675 . . . ? N1 Co1 O1 C10 160.5(7) . . . . ? N7 Co1 O2 C13 -96.8(17) . . . . ? N8 Co1 O2 C13 46.2(4) . . . . ? O1 Co1 O2 C13 -43.4(4) . . . . ? N3 Co1 O2 C13 -138.4(4) 3_675 . . . ? N1 Co1 O2 C13 146.1(4) . . . . ? N7 Co1 N1 C3 -80.1(3) . . . . ? O2 Co1 N1 C3 95.3(3) . . . . ? N8 Co1 N1 C3 -174.6(3) . . . . ? O1 Co1 N1 C3 30.7(9) . . . . ? N3 Co1 N1 C3 4.4(3) 3_675 . . . ? N7 Co1 N1 C1 98.4(4) . . . . ? O2 Co1 N1 C1 -86.1(4) . . . . ? N8 Co1 N1 C1 4.0(4) . . . . ? O1 Co1 N1 C1 -150.7(6) . . . . ? N3 Co1 N1 C1 -177.0(4) 3_675 . . . ? O2 Co1 N7 C15 -51(3) . . . . ? N8 Co1 N7 C15 166.4(16) . . . . ? O1 Co1 N7 C15 -104.1(17) . . . . ? N3 Co1 N7 C15 -8.9(16) 3_675 . . . ? N1 Co1 N7 C15 66.1(17) . . . . ? N7 Co1 N8 C16 47.3(11) . . . . ? O2 Co1 N8 C16 -129.7(11) . . . . ? O1 Co1 N8 C16 -41.9(11) . . . . ? N3 Co1 N8 C16 131.0(18) 3_675 . . . ? N1 Co1 N8 C16 142.5(11) . . . . ? C4 N5 C1 N2 -2.2(7) . . . . ? C4 N5 C1 N1 178.8(4) . . . . ? C2 N2 C1 N5 -180.0(4) . . . . ? C2 N2 C1 N1 -1.0(7) . . . . ? C3 N1 C1 N5 -178.4(4) . . . . ? Co1 N1 C1 N5 3.0(6) . . . . ? C3 N1 C1 N2 2.6(6) . . . . ? Co1 N1 C1 N2 -176.0(3) . . . . ? C1 N2 C2 N4 179.4(5) . . . . ? C1 N2 C2 N3 -0.8(7) . . . . ? C3 N3 C2 N4 -179.4(5) . . . . ? Co1 N3 C2 N4 6.4(7) 3_675 . . . ? C3 N3 C2 N2 0.9(7) . . . . ? Co1 N3 C2 N2 -173.3(4) 3_675 . . . ? C2 N3 C3 N1 1.0(7) . . . . ? Co1 N3 C3 N1 176.0(4) 3_675 . . . ? C2 N3 C3 C3 -178.8(5) . . . 3_675 ? Co1 N3 C3 C3 -3.8(6) 3_675 . . 3_675 ? C1 N1 C3 N3 -2.7(7) . . . . ? Co1 N1 C3 N3 176.2(4) . . . . ? C1 N1 C3 C3 177.2(5) . . . 3_675 ? Co1 N1 C3 C3 -4.0(6) . . . 3_675 ? C1 N5 C4 C9 -16.2(8) . . . . ? C1 N5 C4 C5 166.1(5) . . . . ? C9 C4 C5 C6 -0.4(8) . . . . ? N5 C4 C5 C6 177.4(5) . . . . ? C4 C5 C6 C7 0.1(9) . . . . ? C5 C6 C7 C8 -1.0(10) . . . . ? C6 C7 C8 C9 2.1(9) . . . . ? C5 C4 C9 C8 1.6(8) . . . . ? N5 C4 C9 C8 -176.1(5) . . . . ? C7 C8 C9 C4 -2.5(8) . . . . ? Co1 O1 C10 N6 169.2(4) . . . . ? C12 N6 C10 O1 -179.5(5) . . . . ? C11 N6 C10 O1 -2.3(8) . . . . ? Co1 O2 C13 C14B -133(3) . . . . ? Co1 O2 C13 C14A -125(3) . . . . ? Co1 O2 C13 C14C -107.3(19) . . . . ? Co1 N7 C15 S1 -59(12) . . . . ? Co1 N8 C16 S2 -21(31) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2H O3 0.78(4) 1.90(5) 2.663(6) 165(6) . O3 H3H S1 0.79(5) 2.53(5) 3.296(5) 164(7) 3_675 N4 H4A S1 0.87 2.55 3.405(5) 167.6 1_455 N5 H5B N8 0.87 2.07 2.930(6) 168.5 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.420 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.067 #===END data_jen02_complex_3 _database_code_depnum_ccdc_archive 'CCDC 806770' #TrackingRef '- cifs_complexes 2-5_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H46 N16 Ni2 O18' _chemical_formula_weight 1012.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 9.10730(10) _cell_length_b 9.48280(10) _cell_length_c 13.0297(2) _cell_angle_alpha 106.2700(10) _cell_angle_beta 92.7070(10) _cell_angle_gamma 93.2830(10) _cell_volume 1076.09(2) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5236 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.20 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7287 _exptl_absorpt_correction_T_max 0.7943 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8858 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4192 _reflns_number_gt 3798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.4416P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4192 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.002 _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 Ni1 Ni 0.36477(2) 1.02896(2) 0.308243(17) 0.02266(8) Uani 1 1 d . . . O1 O 0.52794(16) 0.91627(17) 0.22428(12) 0.0341(3) Uani 1 1 d . . . H1H H 0.552(3) 0.868(3) 0.248(2) 0.038(7) Uiso 1 1 d . . . O2 O 0.18695(15) 1.13524(17) 0.37619(12) 0.0323(3) Uani 1 1 d . . . H2H H 0.211(3) 1.188(3) 0.428(2) 0.040(8) Uiso 1 1 d . . . O3 O 0.38392(14) 1.18090(14) 0.22400(10) 0.0312(3) Uani 1 1 d . . . O4 O 0.21112(14) 0.90189(14) 0.18869(10) 0.0318(3) Uani 1 1 d . . . O5 O 0.2688(2) 0.69696(18) 0.07970(14) 0.0623(5) Uani 1 1 d . . . O6 O 0.2861(3) 0.8945(2) 0.03156(13) 0.0734(6) Uani 1 1 d . . . O7 O 0.59804(18) 0.67014(19) 0.29644(14) 0.0549(4) Uani 1 1 d . . . O8 O 0.75027(19) 0.85131(17) 0.38279(13) 0.0502(4) Uani 1 1 d . . . O9 O 0.72452(17) 0.65663(15) 0.43756(12) 0.0420(4) Uani 1 1 d . . . N1 N 0.36405(15) 0.88397(15) 0.40631(11) 0.0217(3) Uani 1 1 d . . . N2 N 0.48545(15) 0.85644(15) 0.56424(11) 0.0216(3) Uani 1 1 d . . . N3 N 0.30294(16) 0.67130(16) 0.46431(12) 0.0262(3) Uani 1 1 d . . . N4 N 0.4315(2) 0.64044(19) 0.60921(14) 0.0331(4) Uani 1 1 d . . . H4NB H 0.490(2) 0.675(2) 0.6655(19) 0.037(6) Uiso 1 1 d . . . H4NA H 0.385(3) 0.558(3) 0.5960(19) 0.044(7) Uiso 1 1 d . . . N5 N 0.18317(17) 0.71013(17) 0.31539(13) 0.0295(4) Uani 1 1 d . . . H5N H 0.185(3) 0.761(3) 0.2743(19) 0.045(7) Uiso 1 1 d . . . N6 N 0.29196(19) 1.28884(19) 0.10376(13) 0.0353(4) Uani 1 1 d . . . N7 N 0.2572(2) 0.8284(2) 0.09608(13) 0.0408(4) Uani 1 1 d . . . N8 N 0.69143(19) 0.72579(19) 0.37121(14) 0.0361(4) Uani 1 1 d . . . C1 C 0.45745(17) 0.92716(17) 0.49163(13) 0.0196(3) Uani 1 1 d . . . C2 C 0.40553(18) 0.72233(19) 0.54476(14) 0.0232(3) Uani 1 1 d . . . C3 C 0.28420(18) 0.75167(18) 0.39713(14) 0.0231(3) Uani 1 1 d . . . C4 C 0.07259(19) 0.59230(19) 0.28736(15) 0.0271(4) Uani 1 1 d . . . C5 C 0.0603(2) 0.4788(2) 0.3341(2) 0.0469(6) Uani 1 1 d . . . H5A H 0.1283 0.4749 0.3896 0.056 Uiso 1 1 calc R . . C6 C -0.0540(3) 0.3708(3) 0.2979(2) 0.0568(7) Uani 1 1 d . . . H6A H -0.0636 0.2940 0.3302 0.068 Uiso 1 1 calc R . . C7 C -0.1535(2) 0.3729(2) 0.21636(19) 0.0428(5) Uani 1 1 d . . . H7A H -0.2287 0.2970 0.1918 0.051 Uiso 1 1 calc R . . C8 C -0.1424(2) 0.4868(2) 0.17082(17) 0.0388(5) Uani 1 1 d . . . H8A H -0.2109 0.4902 0.1154 0.047 Uiso 1 1 calc R . . C9 C -0.0303(2) 0.5964(2) 0.20663(16) 0.0358(4) Uani 1 1 d . . . H9A H -0.0236 0.6749 0.1759 0.043 Uiso 1 1 calc R . . C10 C 0.6466(3) 0.9848(3) 0.1850(2) 0.0590(7) Uani 1 1 d . . . H10A H 0.7202 0.9148 0.1614 0.089 Uiso 1 1 calc R . . H10B H 0.6904 1.0686 0.2415 0.089 Uiso 1 1 calc R . . H10C H 0.6104 1.0180 0.1252 0.089 Uiso 1 1 calc R . . C11 C 0.0506(2) 1.0580(3) 0.3857(2) 0.0461(5) Uani 1 1 d . . . H11A H -0.0111 1.1255 0.4316 0.069 Uiso 1 1 calc R . . H11B H 0.0704 0.9786 0.4167 0.069 Uiso 1 1 calc R . . H11C H 0.0002 1.0177 0.3154 0.069 Uiso 1 1 calc R . . C12 C 0.2802(2) 1.2017(2) 0.16445(15) 0.0315(4) Uani 1 1 d . . . H12A H 0.1882 1.1510 0.1637 0.038 Uiso 1 1 calc R . . C13 C 0.1665(3) 1.3079(3) 0.03657(19) 0.0532(6) Uani 1 1 d . . . H13A H 0.0809 1.2492 0.0473 0.080 Uiso 1 1 calc R . . H13B H 0.1892 1.2763 -0.0381 0.080 Uiso 1 1 calc R . . H13C H 0.1459 1.4110 0.0558 0.080 Uiso 1 1 calc R . . C14 C 0.4291(3) 1.3708(3) 0.0995(3) 0.0715(9) Uani 1 1 d . . . H14A H 0.5017 1.3551 0.1514 0.107 Uiso 1 1 calc R . . H14B H 0.4134 1.4749 0.1162 0.107 Uiso 1 1 calc R . . H14C H 0.4643 1.3375 0.0282 0.107 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 Ni1 0.02754(13) 0.02115(13) 0.02051(13) 0.00980(9) -0.00410(8) -0.00321(9) O1 0.0406(8) 0.0335(8) 0.0321(8) 0.0148(7) 0.0049(6) 0.0044(6) O2 0.0326(7) 0.0337(8) 0.0316(8) 0.0113(7) -0.0011(6) 0.0019(6) O3 0.0388(7) 0.0287(7) 0.0287(7) 0.0160(6) -0.0076(5) -0.0058(5) O4 0.0402(7) 0.0308(7) 0.0238(7) 0.0101(6) -0.0069(5) -0.0078(6) O5 0.0993(14) 0.0325(9) 0.0485(10) 0.0019(8) 0.0088(10) -0.0044(9) O6 0.1312(18) 0.0612(12) 0.0325(9) 0.0225(9) 0.0148(10) -0.0075(12) O7 0.0472(9) 0.0545(11) 0.0538(10) 0.0011(8) -0.0103(8) 0.0110(8) O8 0.0652(10) 0.0333(8) 0.0569(10) 0.0206(8) 0.0085(8) -0.0002(7) O9 0.0574(9) 0.0284(8) 0.0423(8) 0.0135(7) 0.0027(7) 0.0028(7) N1 0.0252(7) 0.0186(7) 0.0216(7) 0.0081(6) -0.0028(5) -0.0035(5) N2 0.0255(7) 0.0182(7) 0.0220(7) 0.0088(6) -0.0021(6) -0.0026(5) N3 0.0312(8) 0.0223(8) 0.0264(8) 0.0117(6) -0.0062(6) -0.0063(6) N4 0.0445(10) 0.0247(9) 0.0315(9) 0.0162(7) -0.0144(7) -0.0128(7) N5 0.0355(8) 0.0249(8) 0.0297(8) 0.0151(7) -0.0114(7) -0.0097(6) N6 0.0453(10) 0.0352(9) 0.0301(9) 0.0176(8) -0.0028(7) 0.0049(7) N7 0.0547(11) 0.0398(11) 0.0249(9) 0.0090(8) -0.0077(8) -0.0134(8) N8 0.0370(9) 0.0316(9) 0.0387(10) 0.0064(8) 0.0082(7) 0.0080(7) C1 0.0218(8) 0.0174(8) 0.0199(8) 0.0061(7) 0.0010(6) -0.0001(6) C2 0.0270(8) 0.0196(8) 0.0233(9) 0.0081(7) -0.0007(7) -0.0024(7) C3 0.0257(8) 0.0200(9) 0.0234(9) 0.0071(7) -0.0009(7) -0.0024(7) C4 0.0278(9) 0.0212(9) 0.0300(10) 0.0055(8) -0.0050(7) -0.0038(7) C5 0.0440(12) 0.0384(12) 0.0625(15) 0.0295(12) -0.0251(11) -0.0151(9) C6 0.0530(14) 0.0397(13) 0.0845(19) 0.0386(14) -0.0258(13) -0.0208(10) C7 0.0358(11) 0.0335(11) 0.0554(14) 0.0123(10) -0.0108(10) -0.0139(9) C8 0.0349(10) 0.0434(12) 0.0353(11) 0.0113(10) -0.0116(8) -0.0109(9) C9 0.0402(11) 0.0341(11) 0.0340(11) 0.0155(9) -0.0094(8) -0.0089(8) C10 0.0550(15) 0.0562(16) 0.0755(19) 0.0296(15) 0.0313(14) 0.0069(12) C11 0.0353(11) 0.0485(13) 0.0606(15) 0.0246(12) 0.0100(10) 0.0031(10) C12 0.0379(10) 0.0285(10) 0.0293(10) 0.0117(8) -0.0029(8) -0.0005(8) C13 0.0630(15) 0.0579(15) 0.0460(13) 0.0256(12) -0.0094(11) 0.0198(12) C14 0.0647(17) 0.084(2) 0.089(2) 0.0683(19) -0.0076(15) -0.0139(15) _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 Ni1 O3 2.0462(12) . ? Ni1 O1 2.0561(15) . ? Ni1 O2 2.0603(14) . ? Ni1 O4 2.0943(13) . ? Ni1 N2 2.0992(14) 2_676 ? Ni1 N1 2.1231(13) . ? O1 C10 1.418(3) . ? O1 H1H 0.66(2) . ? O2 C11 1.434(2) . ? O2 H2H 0.74(2) . ? O3 C12 1.253(2) . ? O4 N7 1.315(2) . ? O5 N7 1.216(2) . ? O6 N7 1.211(2) . ? O7 N8 1.238(2) . ? O8 N8 1.243(2) . ? O9 N8 1.259(2) . ? N1 C1 1.320(2) . ? N1 C3 1.386(2) . ? N2 C1 1.327(2) . ? N2 C2 1.381(2) . ? N2 Ni1 2.0992(14) 2_676 ? N3 C3 1.323(2) . ? N3 C2 1.333(2) . ? N4 C2 1.316(2) . ? N4 H4NB 0.86(2) . ? N4 H4NA 0.84(3) . ? N5 C3 1.329(2) . ? N5 C4 1.416(2) . ? N5 H5N 0.81(2) . ? N6 C12 1.297(2) . ? N6 C14 1.445(3) . ? N6 C13 1.457(3) . ? C1 C1 1.500(3) 2_676 ? C4 C5 1.379(3) . ? C4 C9 1.385(2) . ? C5 C6 1.384(3) . ? C5 H5A 0.9400 . ? C6 C7 1.368(3) . ? C6 H6A 0.9400 . ? C7 C8 1.372(3) . ? C7 H7A 0.9400 . ? C8 C9 1.379(3) . ? C8 H8A 0.9400 . ? C9 H9A 0.9400 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9400 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Ni1 O1 89.90(6) . . ? O3 Ni1 O2 87.52(5) . . ? O1 Ni1 O2 173.50(6) . . ? O3 Ni1 O4 89.26(5) . . ? O1 Ni1 O4 88.26(6) . . ? O2 Ni1 O4 85.75(6) . . ? O3 Ni1 N2 95.65(5) . 2_676 ? O1 Ni1 N2 92.35(6) . 2_676 ? O2 Ni1 N2 93.84(6) . 2_676 ? O4 Ni1 N2 175.06(5) . 2_676 ? O3 Ni1 N1 173.96(5) . . ? O1 Ni1 N1 89.36(6) . . ? O2 Ni1 N1 93.84(5) . . ? O4 Ni1 N1 96.71(5) . . ? N2 Ni1 N1 78.39(5) 2_676 . ? C10 O1 Ni1 123.76(14) . . ? C10 O1 H1H 110(2) . . ? Ni1 O1 H1H 110(2) . . ? C11 O2 Ni1 122.68(13) . . ? C11 O2 H2H 109.3(19) . . ? Ni1 O2 H2H 109.9(19) . . ? C12 O3 Ni1 122.51(12) . . ? N7 O4 Ni1 119.24(11) . . ? C1 N1 C3 113.85(13) . . ? C1 N1 Ni1 114.21(10) . . ? C3 N1 Ni1 131.93(11) . . ? C1 N2 C2 113.90(14) . . ? C1 N2 Ni1 114.84(11) . 2_676 ? C2 N2 Ni1 131.19(11) . 2_676 ? C3 N3 C2 117.06(14) . . ? C2 N4 H4NB 119.7(15) . . ? C2 N4 H4NA 118.3(16) . . ? H4NB N4 H4NA 122(2) . . ? C3 N5 C4 130.98(15) . . ? C3 N5 H5N 114.7(17) . . ? C4 N5 H5N 114.3(17) . . ? C12 N6 C14 121.79(17) . . ? C12 N6 C13 121.12(19) . . ? C14 N6 C13 117.09(18) . . ? O6 N7 O5 123.3(2) . . ? O6 N7 O4 118.64(18) . . ? O5 N7 O4 118.06(17) . . ? O7 N8 O8 120.40(18) . . ? O7 N8 O9 119.94(18) . . ? O8 N8 O9 119.63(18) . . ? N1 C1 N2 127.62(15) . . ? N1 C1 C1 116.30(17) . 2_676 ? N2 C1 C1 116.08(17) . 2_676 ? N4 C2 N3 118.08(16) . . ? N4 C2 N2 118.34(16) . . ? N3 C2 N2 123.57(14) . . ? N3 C3 N5 121.14(15) . . ? N3 C3 N1 123.84(15) . . ? N5 C3 N1 115.02(14) . . ? C5 C4 C9 119.39(17) . . ? C5 C4 N5 125.41(16) . . ? C9 C4 N5 115.20(16) . . ? C4 C5 C6 118.83(18) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C7 C6 C5 121.8(2) . . ? C7 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? C6 C7 C8 119.34(19) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C7 C8 C9 119.73(18) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C8 C9 C4 120.89(18) . . ? C8 C9 H9A 119.6 . . ? C4 C9 H9A 119.6 . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 N6 124.07(18) . . ? O3 C12 H12A 118.0 . . ? N6 C12 H12A 118.0 . . ? N6 C13 H13A 109.5 . . ? N6 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N6 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N6 C14 H14A 109.5 . . ? N6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Ni1 O1 C10 31.58(18) . . . . ? O2 Ni1 O1 C10 98.1(5) . . . . ? O4 Ni1 O1 C10 120.84(18) . . . . ? N2 Ni1 O1 C10 -64.07(18) 2_676 . . . ? N1 Ni1 O1 C10 -142.42(18) . . . . ? O3 Ni1 O2 C11 133.82(15) . . . . ? O1 Ni1 O2 C11 67.2(5) . . . . ? O4 Ni1 O2 C11 44.38(15) . . . . ? N2 Ni1 O2 C11 -130.68(15) 2_676 . . . ? N1 Ni1 O2 C11 -52.07(16) . . . . ? O1 Ni1 O3 C12 117.66(15) . . . . ? O2 Ni1 O3 C12 -56.38(16) . . . . ? O4 Ni1 O3 C12 29.40(15) . . . . ? N2 Ni1 O3 C12 -149.99(15) 2_676 . . . ? N1 Ni1 O3 C12 -159.4(5) . . . . ? O3 Ni1 O4 N7 73.84(13) . . . . ? O1 Ni1 O4 N7 -16.08(13) . . . . ? O2 Ni1 O4 N7 161.40(13) . . . . ? N2 Ni1 O4 N7 -113.2(6) 2_676 . . . ? N1 Ni1 O4 N7 -105.23(13) . . . . ? O3 Ni1 N1 C1 6.2(6) . . . . ? O1 Ni1 N1 C1 89.09(12) . . . . ? O2 Ni1 N1 C1 -96.57(12) . . . . ? O4 Ni1 N1 C1 177.27(12) . . . . ? N2 Ni1 N1 C1 -3.43(12) 2_676 . . . ? O3 Ni1 N1 C3 -173.4(5) . . . . ? O1 Ni1 N1 C3 -90.48(16) . . . . ? O2 Ni1 N1 C3 83.86(16) . . . . ? O4 Ni1 N1 C3 -2.30(16) . . . . ? N2 Ni1 N1 C3 176.99(16) 2_676 . . . ? Ni1 O4 N7 O6 -78.5(2) . . . . ? Ni1 O4 N7 O5 101.39(19) . . . . ? C3 N1 C1 N2 2.8(3) . . . . ? Ni1 N1 C1 N2 -176.87(14) . . . . ? C3 N1 C1 C1 -177.54(17) . . . 2_676 ? Ni1 N1 C1 C1 2.8(2) . . . 2_676 ? C2 N2 C1 N1 0.3(3) . . . . ? Ni1 N2 C1 N1 -177.05(14) 2_676 . . . ? C2 N2 C1 C1 -179.38(17) . . . 2_676 ? Ni1 N2 C1 C1 3.3(2) 2_676 . . 2_676 ? C3 N3 C2 N4 -176.46(17) . . . . ? C3 N3 C2 N2 3.8(3) . . . . ? C1 N2 C2 N4 176.42(16) . . . . ? Ni1 N2 C2 N4 -6.8(3) 2_676 . . . ? C1 N2 C2 N3 -3.8(2) . . . . ? Ni1 N2 C2 N3 172.98(13) 2_676 . . . ? C2 N3 C3 N5 -179.18(17) . . . . ? C2 N3 C3 N1 -0.2(3) . . . . ? C4 N5 C3 N3 6.4(3) . . . . ? C4 N5 C3 N1 -172.64(18) . . . . ? C1 N1 C3 N3 -2.8(2) . . . . ? Ni1 N1 C3 N3 176.75(13) . . . . ? C1 N1 C3 N5 176.18(16) . . . . ? Ni1 N1 C3 N5 -4.2(2) . . . . ? C3 N5 C4 C5 -10.0(3) . . . . ? C3 N5 C4 C9 169.3(2) . . . . ? C9 C4 C5 C6 0.8(4) . . . . ? N5 C4 C5 C6 -179.9(2) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 -1.7(4) . . . . ? C6 C7 C8 C9 0.9(4) . . . . ? C7 C8 C9 C4 0.7(3) . . . . ? C5 C4 C9 C8 -1.6(3) . . . . ? N5 C4 C9 C8 179.02(19) . . . . ? Ni1 O3 C12 N6 -174.54(15) . . . . ? C14 N6 C12 O3 0.2(3) . . . . ? C13 N6 C12 O3 -179.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1H O7 0.66(2) 2.19(2) 2.843(2) 166(3) . O1 H1H O8 0.66(2) 2.50(2) 3.034(2) 140(3) . O2 H2H O8 0.74(2) 2.60(2) 3.131(2) 130(2) 2_676 O2 H2H O9 0.74(2) 1.98(3) 2.717(2) 176(3) 2_676 N4 H4NB O3 0.86(2) 1.95(2) 2.772(2) 159(2) 2_676 N4 H4NA O9 0.84(3) 2.13(3) 2.970(2) 178(2) 2_666 N5 H5N O4 0.81(2) 1.98(2) 2.7867(19) 172(2) . N5 H5N O5 0.81(2) 2.60(2) 3.174(2) 129(2) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.267 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.051 #===END data_js001_complex_4 _database_code_depnum_ccdc_archive 'CCDC 806771' #TrackingRef '- cifs_complexes 2-5_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H38 Cl4 Cu2 N12 O4' _chemical_formula_weight 851.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3414(2) _cell_length_b 10.4430(2) _cell_length_c 10.5451(2) _cell_angle_alpha 66.8280(10) _cell_angle_beta 89.8480(10) _cell_angle_gamma 62.3640(10) _cell_volume 904.60(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5788 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.74 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 1.521 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7820 _exptl_absorpt_correction_T_max 0.8505 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8350 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.74 _reflns_number_total 3038 _reflns_number_gt 2682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (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 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.0998P] 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 3038 _refine_ls_number_parameters 229 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.69990(3) 0.67918(3) 0.50325(3) 0.03679(11) Uani 1 1 d . . . Cl1 Cl 0.62962(6) 0.57393(7) 0.71142(6) 0.04955(16) Uani 1 1 d . . . Cl2 Cl 0.66516(8) 0.93353(7) 0.38558(7) 0.05792(18) Uani 1 1 d . . . N1 N 0.90686(18) 0.5998(2) 0.60372(17) 0.0327(4) Uani 1 1 d . . . N2 N 1.15999(18) 0.4834(2) 0.58361(18) 0.0332(4) Uani 1 1 d . . . N3 N 1.08318(19) 0.6125(2) 0.73531(19) 0.0383(4) Uani 1 1 d . . . N4 N 1.3217(2) 0.5138(3) 0.7032(2) 0.0539(5) Uani 1 1 d . . . H4A H 1.3416 0.5469 0.7594 0.065 Uiso 1 1 calc R . . H4B H 1.3902 0.4654 0.6655 0.065 Uiso 1 1 calc R . . N5 N 0.83979(19) 0.6992(2) 0.76712(19) 0.0403(4) Uani 1 1 d . . . H5B H 0.7524 0.7225 0.7320 0.048 Uiso 1 1 calc R . . N6 N 0.2619(2) 0.8653(2) 0.3567(2) 0.0451(5) Uani 1 1 d . . . O1 O 0.51268(16) 0.7386(2) 0.39154(17) 0.0488(4) Uani 1 1 d . . . C1 C 1.0191(2) 0.5234(2) 0.5529(2) 0.0305(4) Uani 1 1 d . . . C2 C 1.1867(2) 0.5371(3) 0.6750(2) 0.0360(5) Uani 1 1 d . . . C3 C 0.9478(2) 0.6362(2) 0.7037(2) 0.0324(4) Uani 1 1 d . . . C4 C 0.8474(2) 0.7335(3) 0.8839(2) 0.0374(5) Uani 1 1 d . . . C5 C 0.9766(3) 0.7001(3) 0.9597(2) 0.0465(6) Uani 1 1 d . . . H5A H 1.0677 0.6524 0.9354 0.056 Uiso 1 1 calc R . . C6 C 0.9699(3) 0.7379(3) 1.0723(3) 0.0540(6) Uani 1 1 d . . . H6A H 1.0569 0.7171 1.1224 0.065 Uiso 1 1 calc R . . C7 C 0.8362(3) 0.8061(3) 1.1114(3) 0.0583(7) Uani 1 1 d . . . H7A H 0.8328 0.8319 1.1868 0.070 Uiso 1 1 calc R . . C8 C 0.7086(3) 0.8355(3) 1.0382(3) 0.0624(7) Uani 1 1 d . . . H8A H 0.6189 0.8782 1.0661 0.075 Uiso 1 1 calc R . . C9 C 0.7117(3) 0.8020(3) 0.9222(3) 0.0531(6) Uani 1 1 d . . . H9A H 0.6242 0.8251 0.8711 0.064 Uiso 1 1 calc R . . C10 C 0.3930(2) 0.8222(3) 0.4184(3) 0.0468(6) Uani 1 1 d . . . H10A H 0.3987 0.8556 0.4870 0.056 Uiso 1 1 calc R . . C11 C 0.2429(3) 0.8272(4) 0.2429(4) 0.0821(10) Uani 1 1 d . . . H11A H 0.3386 0.7713 0.2232 0.123 Uiso 1 1 calc R . . H11B H 0.1786 0.9250 0.1599 0.123 Uiso 1 1 calc R . . H11C H 0.1988 0.7599 0.2701 0.123 Uiso 1 1 calc R . . C12 C 0.1289(3) 0.9504(3) 0.4032(3) 0.0662(8) Uani 1 1 d . . . H12A H 0.1573 0.9683 0.4786 0.099 Uiso 1 1 calc R . . H12B H 0.0816 0.8867 0.4362 0.099 Uiso 1 1 calc R . . H12C H 0.0605 1.0521 0.3256 0.099 Uiso 1 1 calc R . . O2 O 0.3482(5) 0.5899(6) 0.9368(5) 0.0905(13) Uani 0.55 1 d PD A 1 H2A H 0.4376 0.5299 0.9742 0.136 Uiso 0.55 1 calc PR A 1 C13 C 0.308(3) 0.757(2) 0.8986(13) 0.100(3) Uani 0.55 1 d PD A 1 H13A H 0.2449 0.7944 0.9579 0.149 Uiso 0.55 1 calc PR A 1 H13B H 0.2551 0.8236 0.8015 0.149 Uiso 0.55 1 calc PR A 1 H13C H 0.3970 0.7617 0.9116 0.149 Uiso 0.55 1 calc PR A 1 C14 C 0.338(4) 0.734(3) 0.9418(18) 0.100(3) Uani 0.45 1 d PD B 2 H14A H 0.4437 0.6845 0.9752 0.149 Uiso 0.45 1 calc PR B 2 H14B H 0.3012 0.6704 1.0058 0.149 Uiso 0.45 1 calc PR B 2 H14C H 0.2879 0.8404 0.9364 0.149 Uiso 0.45 1 calc PR B 2 O3 O 0.3103(8) 0.7439(8) 0.8084(7) 0.109(2) Uani 0.45 1 d PD B 2 H3A H 0.3439 0.7960 0.7542 0.164 Uiso 0.45 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02622(15) 0.04401(18) 0.04371(18) -0.02579(14) 0.00741(11) -0.01511(12) Cl1 0.0413(3) 0.0563(4) 0.0546(4) -0.0226(3) 0.0152(3) -0.0288(3) Cl2 0.0710(4) 0.0450(3) 0.0543(4) -0.0218(3) 0.0114(3) -0.0268(3) N1 0.0269(8) 0.0373(9) 0.0385(9) -0.0230(8) 0.0088(7) -0.0146(7) N2 0.0257(8) 0.0398(9) 0.0398(9) -0.0256(8) 0.0083(7) -0.0141(7) N3 0.0325(9) 0.0465(10) 0.0472(10) -0.0326(9) 0.0118(8) -0.0187(8) N4 0.0315(10) 0.0845(15) 0.0755(14) -0.0620(13) 0.0177(10) -0.0296(10) N5 0.0295(9) 0.0558(11) 0.0473(10) -0.0356(10) 0.0118(8) -0.0197(9) N6 0.0302(10) 0.0424(10) 0.0581(12) -0.0250(10) 0.0062(9) -0.0126(8) O1 0.0280(8) 0.0626(10) 0.0606(10) -0.0420(9) 0.0076(7) -0.0143(7) C1 0.0297(10) 0.0326(10) 0.0331(10) -0.0179(9) 0.0073(8) -0.0157(9) C2 0.0290(10) 0.0423(12) 0.0430(12) -0.0260(10) 0.0088(9) -0.0168(9) C3 0.0277(10) 0.0351(11) 0.0390(11) -0.0230(9) 0.0086(9) -0.0138(9) C4 0.0374(11) 0.0394(12) 0.0378(11) -0.0235(10) 0.0111(9) -0.0159(10) C5 0.0412(12) 0.0564(14) 0.0494(13) -0.0342(12) 0.0127(11) -0.0212(11) C6 0.0574(15) 0.0621(16) 0.0476(14) -0.0330(13) 0.0054(12) -0.0268(13) C7 0.0739(18) 0.0553(15) 0.0436(14) -0.0324(13) 0.0136(13) -0.0224(14) C8 0.0581(16) 0.0648(17) 0.0551(15) -0.0386(14) 0.0217(13) -0.0142(14) C9 0.0403(13) 0.0641(16) 0.0535(14) -0.0364(13) 0.0141(11) -0.0167(12) C10 0.0352(12) 0.0519(14) 0.0509(14) -0.0325(12) 0.0056(10) -0.0122(11) C11 0.0552(17) 0.080(2) 0.113(3) -0.065(2) -0.0111(17) -0.0174(16) C12 0.0359(13) 0.0582(16) 0.087(2) -0.0304(16) 0.0192(13) -0.0119(12) O2 0.099(3) 0.109(3) 0.086(3) -0.058(3) 0.024(2) -0.057(3) C13 0.155(12) 0.126(7) 0.050(9) -0.029(7) 0.016(9) -0.102(7) C14 0.155(12) 0.126(7) 0.050(9) -0.029(7) 0.016(9) -0.102(7) O3 0.192(7) 0.156(5) 0.105(4) -0.097(4) 0.104(5) -0.149(5) _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 1.9607(15) . ? Cu1 N1 2.0163(16) . ? Cu1 N2 2.1805(15) 2_766 ? Cu1 Cl2 2.2907(7) . ? Cu1 Cl1 2.3214(6) . ? N1 C1 1.321(2) . ? N1 C3 1.379(2) . ? N2 C1 1.317(3) . ? N2 C2 1.376(3) . ? N2 Cu1 2.1804(15) 2_766 ? N3 C3 1.323(3) . ? N3 C2 1.334(3) . ? N4 C2 1.314(3) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 C3 1.337(2) . ? N5 C4 1.423(3) . ? N5 H5B 0.8600 . ? N6 C10 1.294(3) . ? N6 C11 1.444(3) . ? N6 C12 1.459(3) . ? O1 C10 1.251(3) . ? C1 C1 1.500(4) 2_766 ? C4 C5 1.379(3) . ? C4 C9 1.392(3) . ? C5 C6 1.384(3) . ? C5 H5A 0.9300 . ? C6 C7 1.380(4) . ? C6 H6A 0.9300 . ? C7 C8 1.369(4) . ? C7 H7A 0.9300 . ? C8 C9 1.395(3) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O2 C13 1.465(17) . ? O2 H2A 0.8200 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O3 1.389(14) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O3 H3A 0.8200 . ? 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 N1 172.05(6) . . ? O1 Cu1 N2 93.68(6) . 2_766 ? N1 Cu1 N2 78.38(6) . 2_766 ? O1 Cu1 Cl2 92.69(6) . . ? N1 Cu1 Cl2 90.08(5) . . ? N2 Cu1 Cl2 113.07(5) 2_766 . ? O1 Cu1 Cl1 90.58(5) . . ? N1 Cu1 Cl1 93.60(5) . . ? N2 Cu1 Cl1 118.62(5) 2_766 . ? Cl2 Cu1 Cl1 127.85(2) . . ? C1 N1 C3 113.89(16) . . ? C1 N1 Cu1 116.34(13) . . ? C3 N1 Cu1 128.83(13) . . ? C1 N2 C2 113.52(16) . . ? C1 N2 Cu1 110.99(12) . 2_766 ? C2 N2 Cu1 134.94(13) . 2_766 ? C3 N3 C2 117.16(17) . . ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C3 N5 C4 129.84(18) . . ? C3 N5 H5B 115.1 . . ? C4 N5 H5B 115.1 . . ? C10 N6 C11 121.4(2) . . ? C10 N6 C12 120.5(2) . . ? C11 N6 C12 118.1(2) . . ? C10 O1 Cu1 117.42(14) . . ? N2 C1 N1 128.07(17) . . ? N2 C1 C1 116.1(2) . 2_766 ? N1 C1 C1 115.8(2) . 2_766 ? N4 C2 N3 118.42(18) . . ? N4 C2 N2 117.88(18) . . ? N3 C2 N2 123.70(18) . . ? N3 C3 N5 121.57(18) . . ? N3 C3 N1 123.22(17) . . ? N5 C3 N1 115.21(17) . . ? C5 C4 C9 120.11(19) . . ? C5 C4 N5 124.93(19) . . ? C9 C4 N5 114.94(19) . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C8 C7 C6 119.4(2) . . ? C8 C7 H7A 120.3 . . ? C6 C7 H7A 120.3 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 H8A 119.6 . . ? C9 C8 H8A 119.6 . . ? C4 C9 C8 119.2(2) . . ? C4 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? O1 C10 N6 124.0(2) . . ? O1 C10 H10A 118.0 . . ? N6 C10 H10A 118.0 . . ? N6 C11 H11A 109.5 . . ? N6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N6 C12 H12A 109.5 . . ? N6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 O2 H2A 109.5 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C14 O3 H3A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N1 C1 10.2(6) . . . . ? N2 Cu1 N1 C1 13.34(14) 2_766 . . . ? Cl2 Cu1 N1 C1 -100.22(14) . . . . ? Cl1 Cu1 N1 C1 131.83(14) . . . . ? O1 Cu1 N1 C3 178.4(4) . . . . ? N2 Cu1 N1 C3 -178.49(19) 2_766 . . . ? Cl2 Cu1 N1 C3 67.94(18) . . . . ? Cl1 Cu1 N1 C3 -60.01(18) . . . . ? N1 Cu1 O1 C10 175.2(4) . . . . ? N2 Cu1 O1 C10 172.18(18) 2_766 . . . ? Cl2 Cu1 O1 C10 -74.49(18) . . . . ? Cl1 Cu1 O1 C10 53.45(18) . . . . ? C2 N2 C1 N1 -3.4(3) . . . . ? Cu1 N2 C1 N1 169.45(17) 2_766 . . . ? C2 N2 C1 C1 176.5(2) . . . 2_766 ? Cu1 N2 C1 C1 -10.6(3) 2_766 . . 2_766 ? C3 N1 C1 N2 -1.9(3) . . . . ? Cu1 N1 C1 N2 168.04(18) . . . . ? C3 N1 C1 C1 178.2(2) . . . 2_766 ? Cu1 N1 C1 C1 -11.9(3) . . . 2_766 ? C3 N3 C2 N4 179.2(2) . . . . ? C3 N3 C2 N2 -0.2(3) . . . . ? C1 N2 C2 N4 -174.8(2) . . . . ? Cu1 N2 C2 N4 14.6(3) 2_766 . . . ? C1 N2 C2 N3 4.5(3) . . . . ? Cu1 N2 C2 N3 -166.01(16) 2_766 . . . ? C2 N3 C3 N5 174.7(2) . . . . ? C2 N3 C3 N1 -5.8(3) . . . . ? C4 N5 C3 N3 -8.2(4) . . . . ? C4 N5 C3 N1 172.3(2) . . . . ? C1 N1 C3 N3 6.8(3) . . . . ? Cu1 N1 C3 N3 -161.59(16) . . . . ? C1 N1 C3 N5 -173.67(18) . . . . ? Cu1 N1 C3 N5 17.9(3) . . . . ? C3 N5 C4 C5 -2.7(4) . . . . ? C3 N5 C4 C9 179.1(2) . . . . ? C9 C4 C5 C6 -1.3(4) . . . . ? N5 C4 C5 C6 -179.4(2) . . . . ? C4 C5 C6 C7 1.1(4) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C6 C7 C8 C9 -2.0(4) . . . . ? C5 C4 C9 C8 -0.2(4) . . . . ? N5 C4 C9 C8 178.1(2) . . . . ? C7 C8 C9 C4 1.9(4) . . . . ? Cu1 O1 C10 N6 -177.46(19) . . . . ? C11 N6 C10 O1 -4.0(4) . . . . ? C12 N6 C10 O1 174.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 24.74 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.328 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.048 #===END data_js007a_complex_5 _database_code_depnum_ccdc_archive 'CCDC 806772' #TrackingRef '- cifs_complexes 2-5_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H37 Cu2 N17 O16' _chemical_formula_weight 970.81 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 C2/c 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 25.2640(4) _cell_length_b 10.8761(2) _cell_length_c 19.8923(6) _cell_angle_alpha 90.00 _cell_angle_beta 127.5490(10) _cell_angle_gamma 90.00 _cell_volume 4333.53(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9856 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.67 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8397 _exptl_absorpt_correction_T_max 0.8919 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 38347 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.72 _reflns_number_total 5494 _reflns_number_gt 4408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (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 'calc w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+4.3864P] 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 5494 _refine_ls_number_parameters 298 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.134779(13) 0.65538(2) 0.313881(17) 0.03204(12) Uani 1 1 d . . . N1 N 0.03301(10) 0.66744(16) 0.19289(11) 0.0303(4) Uani 1 1 d . . . N2 N -0.07870(10) 0.66670(16) 0.14579(12) 0.0306(4) Uani 1 1 d . . . N3 N -0.05670(10) 0.67364(19) 0.04474(12) 0.0357(4) Uani 1 1 d . . . N4 N -0.16330(11) 0.6783(2) 0.00131(13) 0.0475(5) Uani 1 1 d . . . H4A H -0.1770 0.6830 -0.0502 0.057 Uiso 1 1 calc R . . H4B H -0.1917 0.6776 0.0118 0.057 Uiso 1 1 calc R . . N5 N 0.05379(10) 0.6714(2) 0.09599(12) 0.0379(4) Uani 1 1 d . . . H5B H 0.0943 0.6775 0.1413 0.045 Uiso 1 1 calc R . . N6 N 0.20951(14) 0.4657(2) 0.40865(17) 0.0557(6) Uani 1 1 d . . . N7 N 0.14882(14) 1.0334(2) 0.31587(19) 0.0668(8) Uani 1 1 d . . . N8 N 0.28373(12) 0.8528(2) 0.28210(15) 0.0458(5) Uani 1 1 d . . . O1 O 0.23603(17) 0.5680(3) 0.4394(2) 0.0870(8) Uani 1 1 d . . . O2 O 0.15083(13) 0.4692(3) 0.34112(18) 0.0691(6) Uani 1 1 d . . . O3 O 0.2363(2) 0.3690(3) 0.4400(2) 0.1022(11) Uani 1 1 d . . . O4 O 0.16641(11) 0.83093(15) 0.33876(14) 0.0482(5) Uani 1 1 d . . . O5 O 0.17833(9) 0.63787(16) 0.25909(11) 0.0385(4) Uani 1 1 d . . . H5D H 0.1838 0.5519 0.2552 0.058 Uiso 1 1 d R A . H5C H 0.2187 0.6845 0.2748 0.058 Uiso 1 1 d R . . O6 O 0.32663(13) 0.9328(2) 0.31567(18) 0.0796(8) Uani 1 1 d . . . O7 O 0.2372(2) 0.8578(3) 0.20754(18) 0.1099(14) Uani 1 1 d . . . O8 O 0.28869(10) 0.7651(2) 0.32667(12) 0.0539(5) Uani 1 1 d . . . C1 C -0.01258(11) 0.66610(17) 0.20484(12) 0.0278(4) Uani 1 1 d . . . C2 C -0.09907(12) 0.6723(2) 0.06393(14) 0.0339(4) Uani 1 1 d . . . C3 C 0.00752(12) 0.67047(19) 0.10836(14) 0.0319(4) Uani 1 1 d . . . C4 C 0.04655(13) 0.6640(2) 0.01950(15) 0.0348(5) Uani 1 1 d . . . C5 C 0.10551(15) 0.6777(3) 0.02897(18) 0.0477(6) Uani 1 1 d . . . H5A H 0.1453 0.6929 0.0823 0.057 Uiso 1 1 calc R . . C6 C 0.10508(18) 0.6688(3) -0.0410(2) 0.0588(8) Uani 1 1 d . . . H6A H 0.1445 0.6781 -0.0347 0.071 Uiso 1 1 calc R . . C7 C 0.04579(18) 0.6460(3) -0.11999(19) 0.0521(7) Uani 1 1 d . . . H7A H 0.0452 0.6392 -0.1670 0.062 Uiso 1 1 calc R . . C8 C -0.01239(15) 0.6332(2) -0.12920(16) 0.0448(6) Uani 1 1 d . . . H8A H -0.0521 0.6184 -0.1828 0.054 Uiso 1 1 calc R . . C9 C -0.01296(13) 0.6419(2) -0.05991(15) 0.0401(5) Uani 1 1 d . . . H9A H -0.0526 0.6331 -0.0668 0.048 Uiso 1 1 calc R . . C10 C 0.13106(16) 0.9222(3) 0.3130(3) 0.0796(13) Uani 1 1 d . A . H10A H 0.0863 0.9095 0.2885 0.095 Uiso 1 1 calc R . . C11 C 0.2184(2) 1.0638(4) 0.3531(4) 0.0966(15) Uani 1 1 d . A . H11A H 0.2392 0.9944 0.3478 0.145 Uiso 1 1 calc R . . H11B H 0.2422 1.0838 0.4119 0.145 Uiso 1 1 calc R . . H11C H 0.2193 1.1329 0.3237 0.145 Uiso 1 1 calc R . . C12 C 0.1067(8) 1.1343(11) 0.3155(12) 0.114(5) Uani 0.50 1 d P A 1 H12A H 0.1109 1.1298 0.3668 0.172 Uiso 0.50 1 calc PR A 1 H12B H 0.0607 1.1233 0.2676 0.172 Uiso 0.50 1 calc PR A 1 H12C H 0.1218 1.2131 0.3119 0.172 Uiso 0.50 1 calc PR A 1 C12' C 0.1055(6) 1.1402(10) 0.2635(10) 0.115(6) Uani 0.50 1 d P A 2 H12D H 0.1015 1.1440 0.2123 0.172 Uiso 0.50 1 calc PR A 2 H12E H 0.1253 1.2149 0.2950 0.172 Uiso 0.50 1 calc PR A 2 H12F H 0.0621 1.1300 0.2495 0.172 Uiso 0.50 1 calc PR A 2 N9 N 0.4675(5) 0.5422(6) 0.6224(7) 0.118(3) Uani 0.50 1 d PU . . C13 C 0.4334(4) 0.5256(6) 0.5432(7) 0.108(4) Uani 0.50 1 d PU . . C14 C 0.3831(6) 0.5152(9) 0.4535(7) 0.118(4) Uani 0.50 1 d PU . . H14A H 0.4024 0.4816 0.4283 0.177 Uiso 0.50 1 calc PR . . H14B H 0.3649 0.5950 0.4300 0.177 Uiso 0.50 1 calc PR . . H14C H 0.3481 0.4619 0.4420 0.177 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.03397(18) 0.03138(17) 0.03631(18) 0.00034(9) 0.02427(14) 0.00076(9) N1 0.0301(9) 0.0370(9) 0.0261(8) -0.0006(6) 0.0182(7) -0.0002(7) N2 0.0290(9) 0.0374(9) 0.0271(8) 0.0012(6) 0.0181(7) 0.0015(7) N3 0.0349(10) 0.0460(10) 0.0291(9) 0.0019(7) 0.0210(8) 0.0018(8) N4 0.0314(10) 0.0788(15) 0.0291(9) 0.0042(9) 0.0166(9) 0.0062(10) N5 0.0318(10) 0.0557(12) 0.0278(9) -0.0009(8) 0.0190(8) -0.0008(8) N6 0.0651(16) 0.0518(13) 0.0655(15) 0.0217(12) 0.0476(14) 0.0212(12) N7 0.0574(15) 0.0344(12) 0.0805(19) -0.0002(11) 0.0275(14) 0.0029(11) N8 0.0444(12) 0.0506(12) 0.0443(12) 0.0061(9) 0.0280(11) 0.0012(9) O1 0.124(2) 0.0687(16) 0.109(2) -0.0193(15) 0.092(2) -0.0155(16) O2 0.0631(14) 0.0778(16) 0.0801(15) 0.0082(13) 0.0507(13) -0.0010(12) O3 0.127(3) 0.0785(18) 0.124(3) 0.0531(19) 0.089(2) 0.0551(19) O4 0.0521(11) 0.0324(8) 0.0647(12) -0.0051(7) 0.0379(10) -0.0024(7) O5 0.0379(9) 0.0411(8) 0.0449(9) -0.0032(7) 0.0296(8) -0.0018(7) O6 0.0618(14) 0.0704(15) 0.0793(16) 0.0188(12) 0.0289(13) -0.0167(12) O7 0.101(2) 0.124(3) 0.0448(14) 0.0200(14) 0.0136(15) -0.0294(19) O8 0.0500(11) 0.0575(11) 0.0460(10) 0.0087(8) 0.0250(9) -0.0089(9) C1 0.0311(10) 0.0285(9) 0.0252(9) 0.0006(7) 0.0179(8) 0.0007(7) C2 0.0333(11) 0.0387(11) 0.0292(10) 0.0002(8) 0.0188(9) 0.0013(8) C3 0.0359(11) 0.0353(10) 0.0292(10) 0.0001(8) 0.0222(9) 0.0004(8) C4 0.0389(12) 0.0409(11) 0.0312(10) 0.0010(8) 0.0248(10) 0.0012(8) C5 0.0395(13) 0.0701(17) 0.0377(12) -0.0031(11) 0.0257(11) -0.0017(12) C6 0.0553(18) 0.088(2) 0.0522(16) -0.0005(14) 0.0425(15) 0.0004(15) C7 0.0683(19) 0.0618(17) 0.0424(14) 0.0016(11) 0.0422(15) 0.0036(13) C8 0.0522(15) 0.0500(13) 0.0322(11) -0.0006(10) 0.0257(11) 0.0028(11) C9 0.0399(12) 0.0493(13) 0.0345(11) -0.0027(9) 0.0244(10) -0.0030(10) C10 0.0465(17) 0.0424(16) 0.128(4) -0.0055(17) 0.042(2) -0.0007(12) C11 0.083(3) 0.057(2) 0.151(4) 0.002(2) 0.072(3) -0.0060(19) C12 0.105(9) 0.044(4) 0.175(16) 0.020(7) 0.076(11) 0.029(5) C12' 0.065(6) 0.045(4) 0.146(12) 0.022(6) 0.019(7) 0.014(4) N9 0.111(6) 0.041(3) 0.146(6) 0.016(4) 0.050(6) 0.015(4) C13 0.047(4) 0.027(3) 0.135(6) 0.010(4) -0.004(4) -0.004(2) C14 0.106(7) 0.062(5) 0.114(6) -0.002(5) 0.029(6) 0.006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.9739(17) . ? Cu1 O4 2.0117(18) . ? Cu1 N2 2.0129(19) 2 ? Cu1 O2 2.071(3) . ? Cu1 N1 2.2086(19) . ? Cu1 O1 2.429(4) . ? N1 C1 1.310(3) . ? N1 C3 1.387(3) . ? N2 C1 1.334(3) . ? N2 C2 1.378(3) . ? N2 Cu1 2.0131(19) 2 ? N3 C3 1.316(3) . ? N3 C2 1.338(3) . ? N4 C2 1.314(3) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 C3 1.334(3) . ? N5 C4 1.420(3) . ? N5 H5B 0.8600 . ? N6 O3 1.199(3) . ? N6 O2 1.256(4) . ? N6 O1 1.249(4) . ? N7 C10 1.279(4) . ? N7 C11 1.471(5) . ? N7 C12' 1.497(10) . ? N7 C12 1.527(13) . ? N8 O7 1.208(4) . ? N8 O6 1.223(3) . ? N8 O8 1.256(3) . ? O4 C10 1.220(4) . ? O5 H5D 0.9550 . ? O5 H5C 1.0040 . ? C1 C1 1.497(4) 2 ? C4 C5 1.391(4) . ? C4 C9 1.385(4) . ? C5 C6 1.389(4) . ? C5 H5A 0.9300 . ? C6 C7 1.380(5) . ? C6 H6A 0.9300 . ? C7 C8 1.373(4) . ? C7 H7A 0.9300 . ? C8 C9 1.390(3) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? N9 C13 1.266(14) . ? C13 C14 1.431(14) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O4 87.47(8) . . ? O5 Cu1 N2 172.12(7) . 2 ? O4 Cu1 N2 96.57(8) . 2 ? O5 Cu1 O2 87.94(8) . . ? O4 Cu1 O2 151.45(11) . . ? N2 Cu1 O2 91.64(8) 2 . ? O5 Cu1 N1 94.27(7) . . ? O4 Cu1 N1 103.64(8) . . ? N2 Cu1 N1 78.22(7) 2 . ? O2 Cu1 N1 104.80(9) . . ? O5 Cu1 O1 86.43(8) . . ? O4 Cu1 O1 96.14(9) . . ? N2 Cu1 O1 99.81(8) 2 . ? O2 Cu1 O1 55.43(10) . . ? N1 Cu1 O1 160.22(8) . . ? C1 N1 C3 114.22(19) . . ? C1 N1 Cu1 111.71(13) . . ? C3 N1 Cu1 134.00(15) . . ? C1 N2 C2 113.98(19) . . ? C1 N2 Cu1 117.17(14) . 2 ? C2 N2 Cu1 128.83(16) . 2 ? C3 N3 C2 117.20(19) . . ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C3 N5 C4 130.0(2) . . ? C3 N5 H5B 115.0 . . ? C4 N5 H5B 115.0 . . ? O3 N6 O2 120.5(3) . . ? O3 N6 O1 124.2(4) . . ? O2 N6 O1 115.4(3) . . ? C10 N7 C11 121.0(3) . . ? C10 N7 C12' 127.9(6) . . ? C11 N7 C12' 108.5(6) . . ? C10 N7 C12 117.0(6) . . ? C11 N7 C12 117.2(7) . . ? C12' N7 C12 39.4(8) . . ? O7 N8 O6 120.9(3) . . ? O7 N8 O8 120.3(3) . . ? O6 N8 O8 118.8(2) . . ? N6 O1 Cu1 86.0(2) . . ? N6 O2 Cu1 103.0(2) . . ? C10 O4 Cu1 126.1(2) . . ? Cu1 O5 H5D 107.3 . . ? Cu1 O5 H5C 125.6 . . ? H5D O5 H5C 110.4 . . ? N1 C1 N2 127.43(19) . . ? N1 C1 C1 116.1(2) . 2 ? N2 C1 C1 116.4(2) . 2 ? N4 C2 N3 118.0(2) . . ? N4 C2 N2 118.6(2) . . ? N3 C2 N2 123.4(2) . . ? N3 C3 N5 121.9(2) . . ? N3 C3 N1 123.8(2) . . ? N5 C3 N1 114.4(2) . . ? C5 C4 C9 120.1(2) . . ? C5 C4 N5 114.9(2) . . ? C9 C4 N5 125.0(2) . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C7 C6 C5 119.6(3) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C7 C8 C9 121.2(3) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C8 C9 C4 118.9(2) . . ? C8 C9 H9A 120.6 . . ? C4 C9 H9A 120.6 . . ? O4 C10 N7 127.1(3) . . ? O4 C10 H10A 116.4 . . ? N7 C10 H10A 116.4 . . ? N7 C11 H11A 109.5 . . ? N7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N7 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N7 C12' H12D 109.5 . . ? N7 C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? N7 C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? N9 C13 C14 167.6(12) . . ? 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 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 N1 C1 172.65(14) . . . . ? O4 Cu1 N1 C1 -98.92(14) . . . . ? N2 Cu1 N1 C1 -4.92(14) 2 . . . ? O2 Cu1 N1 C1 83.66(15) . . . . ? O1 Cu1 N1 C1 81.3(3) . . . . ? O5 Cu1 N1 C3 -3.91(19) . . . . ? O4 Cu1 N1 C3 84.5(2) . . . . ? N2 Cu1 N1 C3 178.5(2) 2 . . . ? O2 Cu1 N1 C3 -92.9(2) . . . . ? O1 Cu1 N1 C3 -95.2(3) . . . . ? O3 N6 O1 Cu1 176.7(3) . . . . ? O2 N6 O1 Cu1 -4.1(2) . . . . ? O5 Cu1 O1 N6 -87.26(17) . . . . ? O4 Cu1 O1 N6 -174.32(17) . . . . ? N2 Cu1 O1 N6 87.89(17) 2 . . . ? O2 Cu1 O1 N6 2.70(16) . . . . ? N1 Cu1 O1 N6 5.4(3) . . . . ? O3 N6 O2 Cu1 -175.9(3) . . . . ? O1 N6 O2 Cu1 4.9(3) . . . . ? O5 Cu1 O2 N6 84.33(18) . . . . ? O4 Cu1 O2 N6 3.4(3) . . . . ? N2 Cu1 O2 N6 -103.54(18) 2 . . . ? N1 Cu1 O2 N6 178.21(16) . . . . ? O1 Cu1 O2 N6 -2.75(16) . . . . ? O5 Cu1 O4 C10 118.4(3) . . . . ? N2 Cu1 O4 C10 -54.8(3) 2 . . . ? O2 Cu1 O4 C10 -160.6(3) . . . . ? N1 Cu1 O4 C10 24.6(3) . . . . ? O1 Cu1 O4 C10 -155.4(3) . . . . ? C3 N1 C1 N2 0.4(3) . . . . ? Cu1 N1 C1 N2 -176.92(16) . . . . ? C3 N1 C1 C1 -178.48(12) . . . 2 ? Cu1 N1 C1 C1 4.23(13) . . . 2 ? C2 N2 C1 N1 -1.6(3) . . . . ? Cu1 N2 C1 N1 176.93(16) 2 . . . ? C2 N2 C1 C1 177.24(13) . . . 2 ? Cu1 N2 C1 C1 -4.22(15) 2 . . 2 ? C3 N3 C2 N4 178.4(2) . . . . ? C3 N3 C2 N2 -0.6(3) . . . . ? C1 N2 C2 N4 -177.3(2) . . . . ? Cu1 N2 C2 N4 4.4(3) 2 . . . ? C1 N2 C2 N3 1.7(3) . . . . ? Cu1 N2 C2 N3 -176.64(16) 2 . . . ? C2 N3 C3 N5 180.0(2) . . . . ? C2 N3 C3 N1 -0.9(3) . . . . ? C4 N5 C3 N3 -6.7(4) . . . . ? C4 N5 C3 N1 174.1(2) . . . . ? C1 N1 C3 N3 1.0(3) . . . . ? Cu1 N1 C3 N3 177.48(16) . . . . ? C1 N1 C3 N5 -179.79(18) . . . . ? Cu1 N1 C3 N5 -3.3(3) . . . . ? C3 N5 C4 C5 175.0(2) . . . . ? C3 N5 C4 C9 -6.6(4) . . . . ? C9 C4 C5 C6 -0.3(4) . . . . ? N5 C4 C5 C6 178.2(3) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C5 C6 C7 C8 0.5(5) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? C7 C8 C9 C4 0.0(4) . . . . ? C5 C4 C9 C8 0.3(4) . . . . ? N5 C4 C9 C8 -178.0(2) . . . . ? Cu1 O4 C10 N7 -167.4(3) . . . . ? C11 N7 C10 O4 0.1(8) . . . . ? C12' N7 C10 O4 159.7(11) . . . . ? C12 N7 C10 O4 -154.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.72 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.742 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.094