# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Youngmee Kim' _publ_contact_author_email ymeekim@ewha.ac.kr loop_ _publ_author_name 'Youngmee Kim' 'Seong Kim' data_ym625sadc2c _database_code_depnum_ccdc_archive 'CCDC 853983' #TrackingRef '- 1_C2c_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cu2 N3 O8' _chemical_formula_weight 609.54 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 25.667(5) _cell_length_b 13.076(3) _cell_length_c 8.7250(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.07(3) _cell_angle_gamma 90.00 _cell_volume 2916.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1443 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 19.17 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 1.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7863 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2795 _reflns_number_gt 2158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The positions of C and N atoms of a acetonitrile solvent molecule were refined isotropically with half occupancies and with C-C restraints (1.48 \%A) and C-N retraints (1.15 \%A). ; _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^)+(0.0800P)^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 2795 _refine_ls_number_parameters 174 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.292642(16) 0.29674(3) 0.06182(4) 0.02341(17) Uani 1 1 d . . . O11 O 0.25179(11) 0.29209(19) 0.2432(3) 0.0350(6) Uani 1 1 d . . . O12 O 0.17892(11) 0.2172(2) 0.1401(3) 0.0377(6) Uani 1 1 d . . . O13 O 0.18381(10) 0.65509(18) 0.3921(3) 0.0352(6) Uani 1 1 d . . . O14 O 0.25549(11) 0.57623(18) 0.4932(3) 0.0367(6) Uani 1 1 d . . . N21 N 0.35746(11) 0.3660(2) 0.2035(3) 0.0298(7) Uani 1 1 d . . . C11 C 0.20543(15) 0.2625(2) 0.2483(4) 0.0272(8) Uani 1 1 d . . . C12 C 0.17914(16) 0.2847(3) 0.3943(4) 0.0312(8) Uani 1 1 d . . . H12A H 0.1859 0.2285 0.4659 0.037 Uiso 1 1 calc R . . H12B H 0.1416 0.2889 0.3692 0.037 Uiso 1 1 calc R . . C13 C 0.19838(16) 0.3843(3) 0.4719(4) 0.0316(8) Uani 1 1 d . . . H13A H 0.1812 0.3939 0.5655 0.038 Uiso 1 1 calc R . . H13B H 0.2357 0.3795 0.4999 0.038 Uiso 1 1 calc R . . C14 C 0.18730(17) 0.4762(3) 0.3670(4) 0.0369(9) Uani 1 1 d . . . H14A H 0.2001 0.4609 0.2681 0.044 Uiso 1 1 calc R . . H14B H 0.1497 0.4847 0.3501 0.044 Uiso 1 1 calc R . . C15 C 0.21093(14) 0.5772(3) 0.4237(4) 0.0274(8) Uani 1 1 d . . . C21 C 0.39522(17) 0.3088(3) 0.2712(5) 0.0404(10) Uani 1 1 d . . . H21 H 0.3961 0.2399 0.2454 0.048 Uiso 1 1 calc R . . C22 C 0.43319(16) 0.3458(3) 0.3778(5) 0.0451(10) Uani 1 1 d . . . H22 H 0.4593 0.3023 0.4201 0.054 Uiso 1 1 calc R . . C23 C 0.43277(15) 0.4461(3) 0.4219(4) 0.0368(9) Uani 1 1 d . . . C24 C 0.39278(16) 0.5066(3) 0.3509(5) 0.0439(10) Uani 1 1 d . . . H24 H 0.3908 0.5756 0.3757 0.053 Uiso 1 1 calc R . . C25 C 0.35666(15) 0.4647(3) 0.2455(5) 0.0373(9) Uani 1 1 d . . . H25 H 0.3302 0.5065 0.2005 0.045 Uiso 1 1 calc R . . C26 C 0.47480(16) 0.4897(4) 0.5354(5) 0.0476(11) Uani 1 1 d . . . H26A H 0.4623 0.5530 0.5770 0.057 Uiso 1 1 calc R . . H26B H 0.4815 0.4421 0.6201 0.057 Uiso 1 1 calc R . . C2S C 0.4317(4) 0.1158(8) 0.9396(11) 0.060(2) Uiso 0.50 1 d PD . . C1S C 0.4601(7) 0.1920(12) 0.853(2) 0.055(5) Uiso 0.25 1 d PD . . C1S* C 0.4657(8) 0.1079(19) 1.0849(18) 0.076(6) Uiso 0.25 1 d PD . . N1S N 0.4808(9) 0.2489(15) 0.779(3) 0.107(8) Uiso 0.25 1 d PD . . N1S* N 0.4892(13) 0.089(2) 1.200(2) 0.143(11) Uiso 0.25 1 d PD . . 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 0.0243(3) 0.0207(3) 0.0242(3) -0.00256(16) -0.00368(17) -0.00363(17) O11 0.0310(15) 0.0455(16) 0.0283(13) -0.0075(11) 0.0019(11) -0.0059(12) O12 0.0378(16) 0.0426(15) 0.0334(14) -0.0105(11) 0.0064(12) -0.0153(12) O13 0.0333(14) 0.0223(13) 0.0482(15) 0.0016(11) -0.0067(12) 0.0011(11) O14 0.0378(16) 0.0229(13) 0.0464(16) -0.0052(11) -0.0130(13) 0.0014(11) N21 0.0246(16) 0.0312(16) 0.0321(15) -0.0051(13) -0.0049(13) -0.0074(13) C11 0.035(2) 0.0194(16) 0.0273(18) 0.0011(13) 0.0019(15) -0.0020(15) C12 0.040(2) 0.0252(18) 0.0292(18) -0.0016(14) 0.0059(16) -0.0043(16) C13 0.044(2) 0.0276(18) 0.0233(17) -0.0029(14) 0.0009(16) -0.0013(16) C14 0.044(2) 0.0254(19) 0.038(2) -0.0042(16) -0.0108(18) -0.0009(17) C15 0.032(2) 0.0263(18) 0.0234(17) -0.0009(13) -0.0006(15) -0.0015(15) C21 0.037(2) 0.033(2) 0.048(2) -0.0018(17) -0.0151(19) -0.0040(17) C22 0.035(2) 0.044(2) 0.052(2) 0.006(2) -0.0165(19) 0.0005(19) C23 0.029(2) 0.055(2) 0.0265(18) -0.0118(17) 0.0012(15) -0.0091(18) C24 0.030(2) 0.043(2) 0.057(3) -0.025(2) -0.0017(19) -0.0020(18) C25 0.027(2) 0.036(2) 0.048(2) -0.0100(17) -0.0067(17) -0.0042(16) C26 0.032(2) 0.073(3) 0.036(2) -0.021(2) -0.0058(18) -0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O12 1.974(3) 7 ? Cu1 O11 1.975(3) . ? Cu1 O13 1.978(2) 4_545 ? Cu1 O14 1.982(2) 6_565 ? Cu1 N21 2.180(3) . ? Cu1 Cu1 2.6517(10) 7 ? O11 C11 1.256(4) . ? O12 C11 1.261(4) . ? O12 Cu1 1.974(3) 7 ? O13 C15 1.250(4) . ? O13 Cu1 1.979(2) 4 ? O14 C15 1.246(4) . ? O14 Cu1 1.982(2) 6_566 ? N21 C21 1.322(5) . ? N21 C25 1.343(5) . ? C11 C12 1.521(5) . ? C12 C13 1.530(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.522(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.519(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C21 C22 1.374(6) . ? C21 H21 0.9300 . ? C22 C23 1.368(6) . ? C22 H22 0.9300 . ? C23 C24 1.396(6) . ? C23 C26 1.510(5) . ? C24 C25 1.362(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C26 1.507(8) 5_666 ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C2S C1S 1.478(2) . ? C2S C1S* 1.479(2) . ? C1S N1S 1.149(2) . ? C1S* N1S* 1.149(2) . ? N1S N1S 1.14(4) 2_656 ? N1S* N1S* 0.99(2) 2_657 ? 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 O12 Cu1 O11 167.57(11) 7 . ? O12 Cu1 O13 87.97(11) 7 4_545 ? O11 Cu1 O13 89.01(11) . 4_545 ? O12 Cu1 O14 90.78(12) 7 6_565 ? O11 Cu1 O14 89.58(11) . 6_565 ? O13 Cu1 O14 167.53(10) 4_545 6_565 ? O12 Cu1 N21 102.73(11) 7 . ? O11 Cu1 N21 89.50(11) . . ? O13 Cu1 N21 93.99(11) 4_545 . ? O14 Cu1 N21 98.38(10) 6_565 . ? O12 Cu1 Cu1 87.22(8) 7 7 ? O11 Cu1 Cu1 80.45(8) . 7 ? O13 Cu1 Cu1 82.97(8) 4_545 7 ? O14 Cu1 Cu1 84.58(8) 6_565 7 ? N21 Cu1 Cu1 169.53(8) . 7 ? C11 O11 Cu1 127.6(2) . . ? C11 O12 Cu1 119.6(2) . 7 ? C15 O13 Cu1 124.3(2) . 4 ? C15 O14 Cu1 122.3(2) . 6_566 ? C21 N21 C25 116.8(3) . . ? C21 N21 Cu1 120.7(2) . . ? C25 N21 Cu1 121.7(2) . . ? O11 C11 O12 124.7(3) . . ? O11 C11 C12 117.5(3) . . ? O12 C11 C12 117.8(3) . . ? C11 C12 C13 112.6(3) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 111.7(3) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 116.3(3) . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? C13 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? O14 C15 O13 125.8(3) . . ? O14 C15 C14 118.2(3) . . ? O13 C15 C14 116.0(3) . . ? N21 C21 C22 123.5(4) . . ? N21 C21 H21 118.2 . . ? C22 C21 H21 118.2 . . ? C23 C22 C21 120.3(4) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 116.2(3) . . ? C22 C23 C26 121.6(4) . . ? C24 C23 C26 122.1(4) . . ? C25 C24 C23 120.1(4) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? N21 C25 C24 123.0(4) . . ? N21 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C26 C26 C23 112.8(4) 5_666 . ? C26 C26 H26A 109.0 5_666 . ? C23 C26 H26A 109.0 . . ? C26 C26 H26B 109.0 5_666 . ? C23 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C1S C2S C1S* 101.7(14) . . ? N1S C1S C2S 176(2) . . ? N1S* C1S* C2S 171(3) . . ? N1S N1S C1S 135(2) 2_656 . ? N1S* N1S* C1S* 168(2) 2_657 . ? 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 O12 Cu1 O11 C11 -13.2(7) 7 . . . ? O13 Cu1 O11 C11 -89.1(3) 4_545 . . . ? O14 Cu1 O11 C11 78.5(3) 6_565 . . . ? N21 Cu1 O11 C11 176.9(3) . . . . ? Cu1 Cu1 O11 C11 -6.1(3) 7 . . . ? O12 Cu1 N21 C21 -84.5(3) 7 . . . ? O11 Cu1 N21 C21 93.3(3) . . . . ? O13 Cu1 N21 C21 4.3(3) 4_545 . . . ? O14 Cu1 N21 C21 -177.2(3) 6_565 . . . ? Cu1 Cu1 N21 C21 77.0(6) 7 . . . ? O12 Cu1 N21 C25 106.3(3) 7 . . . ? O11 Cu1 N21 C25 -75.9(3) . . . . ? O13 Cu1 N21 C25 -164.9(3) 4_545 . . . ? O14 Cu1 N21 C25 13.6(3) 6_565 . . . ? Cu1 Cu1 N21 C25 -92.2(5) 7 . . . ? Cu1 O11 C11 O12 10.0(5) . . . . ? Cu1 O11 C11 C12 -168.7(2) . . . . ? Cu1 O12 C11 O11 -7.2(5) 7 . . . ? Cu1 O12 C11 C12 171.6(2) 7 . . . ? O11 C11 C12 C13 32.0(5) . . . . ? O12 C11 C12 C13 -146.8(3) . . . . ? C11 C12 C13 C14 60.6(4) . . . . ? C12 C13 C14 C15 -172.3(3) . . . . ? Cu1 O14 C15 O13 -1.9(5) 6_566 . . . ? Cu1 O14 C15 C14 176.1(2) 6_566 . . . ? Cu1 O13 C15 O14 2.9(5) 4 . . . ? Cu1 O13 C15 C14 -175.2(2) 4 . . . ? C13 C14 C15 O14 37.8(5) . . . . ? C13 C14 C15 O13 -144.0(4) . . . . ? C25 N21 C21 C22 -1.3(6) . . . . ? Cu1 N21 C21 C22 -171.0(3) . . . . ? N21 C21 C22 C23 1.5(7) . . . . ? C21 C22 C23 C24 -1.1(6) . . . . ? C21 C22 C23 C26 -178.3(4) . . . . ? C22 C23 C24 C25 0.7(6) . . . . ? C26 C23 C24 C25 177.8(4) . . . . ? C21 N21 C25 C24 0.8(6) . . . . ? Cu1 N21 C25 C24 170.4(3) . . . . ? C23 C24 C25 N21 -0.6(6) . . . . ? C22 C23 C26 C26 77.1(7) . . . 5_666 ? C24 C23 C26 C26 -99.9(6) . . . 5_666 ? C1S* C2S C1S N1S 154(35) . . . . ? C1S C2S C1S* N1S* -157(18) . . . . ? C2S C1S N1S N1S -87(36) . . . 2_656 ? C2S C1S* N1S* N1S* -162(20) . . . 2_657 ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.946 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.091 # Attachment '- 2_Pccn_revised.cif' data_ym629sadpccn _database_code_depnum_ccdc_archive 'CCDC 853984' #TrackingRef '- 2_Pccn_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 Cu2 N2 O9' _chemical_formula_weight 643.62 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 Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 13.042(3) _cell_length_b 28.201(6) _cell_length_c 8.6770(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3191.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1443 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 19.17 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16384 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3095 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The positions of C and O atoms of an acetone solvent molecule were refined isotropically with half occupancies. ; _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^)+(0.0791P)^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 3095 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.04656(3) 0.538769(15) 0.05074(5) 0.02732(18) Uani 1 1 d . . . O11 O 0.17531(18) 0.50574(10) -0.0058(3) 0.0406(7) Uani 1 1 d . . . O12 O 0.09599(19) 0.44026(10) -0.0849(3) 0.0407(7) Uani 1 1 d . . . O13 O 0.45968(19) 0.50076(10) -0.2577(3) 0.0376(6) Uani 1 1 d . . . O14 O 0.5360(2) 0.43513(10) -0.3399(3) 0.0403(7) Uani 1 1 d . . . N21 N 0.1097(2) 0.59747(10) 0.1822(4) 0.0338(7) Uani 1 1 d . . . C11 C 0.1748(3) 0.46516(13) -0.0620(4) 0.0309(8) Uani 1 1 d . . . C12 C 0.2756(3) 0.44378(15) -0.1141(5) 0.0381(9) Uani 1 1 d . . . H12A H 0.2670 0.4097 -0.1216 0.046 Uiso 1 1 calc R . . H12B H 0.2906 0.4555 -0.2168 0.046 Uiso 1 1 calc R . . C13 C 0.3672(3) 0.45370(15) -0.0125(5) 0.0355(9) Uani 1 1 d . . . H13A H 0.3576 0.4382 0.0862 0.043 Uiso 1 1 calc R . . H13B H 0.3721 0.4876 0.0058 0.043 Uiso 1 1 calc R . . C14 C 0.4681(3) 0.43603(16) -0.0861(5) 0.0357(9) Uani 1 1 d . . . H14A H 0.5245 0.4426 -0.0164 0.043 Uiso 1 1 calc R . . H14B H 0.4642 0.4019 -0.0999 0.043 Uiso 1 1 calc R . . C15 C 0.4896(3) 0.45900(14) -0.2394(4) 0.0305(8) Uani 1 1 d . . . C21 C 0.2039(3) 0.59660(14) 0.2425(5) 0.0397(9) Uani 1 1 d . . . H21 H 0.2470 0.5717 0.2151 0.048 Uiso 1 1 calc R . . C22 C 0.2411(3) 0.63044(14) 0.3433(5) 0.0452(10) Uani 1 1 d . . . H22 H 0.3075 0.6281 0.3816 0.054 Uiso 1 1 calc R . . C23 C 0.1791(3) 0.66750(13) 0.3861(4) 0.0386(10) Uani 1 1 d . . . C24 C 0.0804(3) 0.66883(14) 0.3254(6) 0.0469(11) Uani 1 1 d . . . H24 H 0.0357 0.6932 0.3519 0.056 Uiso 1 1 calc R . . C25 C 0.0500(3) 0.63370(15) 0.2258(6) 0.0441(11) Uani 1 1 d . . . H25 H -0.0162 0.6352 0.1862 0.053 Uiso 1 1 calc R . . C26 C 0.2153(4) 0.70734(14) 0.4893(5) 0.0451(11) Uani 1 1 d . . . H26A H 0.2718 0.6963 0.5525 0.054 Uiso 1 1 calc R . . H26B H 0.1599 0.7168 0.5574 0.054 Uiso 1 1 calc R . . C27 C 0.2500 0.7500 0.3945(7) 0.0471(15) Uani 1 2 d S . . H27A H 0.3061 0.7402 0.3285 0.057 Uiso 0.50 1 calc PR . . H27B H 0.1938 0.7598 0.3285 0.057 Uiso 0.50 1 calc PR . . O1S O 0.9082(12) 0.7314(6) 1.0186(19) 0.166(5) Uiso 0.50 1 d P . . C1S C 0.8923(10) 0.7021(5) 0.9222(15) 0.075(3) Uiso 0.50 1 d P . . C2S C 0.9642(11) 0.6906(6) 0.820(2) 0.106(5) Uiso 0.50 1 d P . . H2S1 H 1.0281 0.7048 0.8493 0.159 Uiso 0.50 1 calc PR . . H2S2 H 0.9445 0.7019 0.7199 0.159 Uiso 0.50 1 calc PR . . H2S3 H 0.9718 0.6567 0.8171 0.159 Uiso 0.50 1 calc PR . . C3S C 0.7968(15) 0.6798(7) 0.917(2) 0.138(6) Uiso 0.50 1 d P . . H3S1 H 0.7530 0.6930 0.9949 0.207 Uiso 0.50 1 calc PR . . H3S2 H 0.8053 0.6465 0.9352 0.207 Uiso 0.50 1 calc PR . . H3S3 H 0.7665 0.6846 0.8174 0.207 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 0.0245(3) 0.0291(3) 0.0283(3) -0.00264(19) -0.00229(18) -0.00426(17) O11 0.0286(14) 0.0430(17) 0.0501(18) -0.0063(13) 0.0039(13) -0.0046(12) O12 0.0246(13) 0.0434(15) 0.0540(19) -0.0058(13) -0.0012(13) -0.0012(12) O13 0.0454(16) 0.0354(15) 0.0320(15) -0.0003(12) 0.0018(13) 0.0072(11) O14 0.0441(15) 0.0430(16) 0.0338(16) 0.0046(13) 0.0097(13) 0.0146(12) N21 0.0370(17) 0.0307(17) 0.0338(18) -0.0025(14) -0.0047(15) -0.0097(13) C11 0.0272(18) 0.038(2) 0.027(2) -0.0001(17) -0.0018(15) 0.0016(15) C12 0.0242(19) 0.047(2) 0.043(2) -0.0107(19) 0.0016(18) 0.0022(16) C13 0.030(2) 0.048(2) 0.028(2) 0.0017(17) 0.0022(17) 0.0042(16) C14 0.0293(19) 0.044(2) 0.034(2) 0.0101(18) 0.0005(16) 0.0019(16) C15 0.0193(16) 0.039(2) 0.033(2) 0.0002(18) -0.0049(15) 0.0010(15) C21 0.037(2) 0.034(2) 0.048(3) -0.0034(19) -0.0098(19) 0.0006(16) C22 0.047(2) 0.037(2) 0.051(3) 0.000(2) -0.015(2) -0.0071(18) C23 0.060(3) 0.029(2) 0.026(2) 0.0030(16) -0.0025(19) -0.0152(19) C24 0.053(2) 0.032(2) 0.057(3) -0.007(2) 0.000(2) -0.0011(19) C25 0.034(2) 0.040(2) 0.058(3) -0.008(2) -0.004(2) -0.0015(17) C26 0.067(3) 0.036(2) 0.033(2) -0.0038(18) -0.009(2) -0.016(2) C27 0.075(4) 0.039(3) 0.027(3) 0.000 0.000 -0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O12 1.973(3) 5_565 ? Cu1 O14 1.977(3) 4_464 ? Cu1 O13 1.979(3) 8_656 ? Cu1 O11 1.982(3) . ? Cu1 N21 2.172(3) . ? Cu1 Cu1 2.6516(9) 5_565 ? O11 C11 1.244(4) . ? O12 C11 1.261(5) . ? O12 Cu1 1.973(3) 5_565 ? O13 C15 1.251(4) . ? O13 Cu1 1.979(3) 8_655 ? O14 C15 1.257(5) . ? O14 Cu1 1.977(3) 4_564 ? N21 C21 1.336(5) . ? N21 C25 1.339(5) . ? C11 C12 1.515(5) . ? C12 C13 1.511(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.544(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.506(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C21 C22 1.382(6) . ? C21 H21 0.9300 . ? C22 C23 1.373(6) . ? C22 H22 0.9300 . ? C23 C24 1.391(6) . ? C23 C26 1.512(5) . ? C24 C25 1.373(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.526(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C26 1.526(5) 2_565 ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? O1S C1S 1.194(17) . ? C1S C2S 1.331(18) . ? C1S C3S 1.40(2) . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? C3S H3S1 0.9600 . ? C3S H3S2 0.9600 . ? C3S H3S3 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 O12 Cu1 O14 87.80(12) 5_565 4_464 ? O12 Cu1 O13 89.87(11) 5_565 8_656 ? O14 Cu1 O13 167.39(11) 4_464 8_656 ? O12 Cu1 O11 167.49(11) 5_565 . ? O14 Cu1 O11 90.27(12) 4_464 . ? O13 Cu1 O11 89.32(11) 8_656 . ? O12 Cu1 N21 92.86(12) 5_565 . ? O14 Cu1 N21 103.20(11) 4_464 . ? O13 Cu1 N21 89.28(11) 8_656 . ? O11 Cu1 N21 99.61(11) . . ? O12 Cu1 Cu1 82.28(8) 5_565 5_565 ? O14 Cu1 Cu1 88.16(8) 4_464 5_565 ? O13 Cu1 Cu1 79.25(8) 8_656 5_565 ? O11 Cu1 Cu1 85.31(8) . 5_565 ? N21 Cu1 Cu1 167.51(9) . 5_565 ? C11 O11 Cu1 121.7(2) . . ? C11 O12 Cu1 125.3(2) . 5_565 ? C15 O13 Cu1 129.0(3) . 8_655 ? C15 O14 Cu1 118.4(2) . 4_564 ? C21 N21 C25 116.0(3) . . ? C21 N21 Cu1 122.7(3) . . ? C25 N21 Cu1 120.6(2) . . ? O11 C11 O12 125.3(3) . . ? O11 C11 C12 118.6(3) . . ? O12 C11 C12 116.0(3) . . ? C13 C12 C11 116.0(3) . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? C11 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 111.9(3) . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 112.7(3) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? O13 C15 O14 124.5(4) . . ? O13 C15 C14 117.3(3) . . ? O14 C15 C14 118.2(3) . . ? N21 C21 C22 123.9(4) . . ? N21 C21 H21 118.0 . . ? C22 C21 H21 118.0 . . ? C23 C22 C21 119.4(4) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 117.6(4) . . ? C22 C23 C26 122.8(4) . . ? C24 C23 C26 119.5(4) . . ? C25 C24 C23 119.1(4) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? N21 C25 C24 124.1(4) . . ? N21 C25 H25 118.0 . . ? C24 C25 H25 118.0 . . ? C23 C26 C27 111.0(3) . . ? C23 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? C23 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C26 C27 C26 114.8(5) 2_565 . ? C26 C27 H27A 108.6 2_565 . ? C26 C27 H27A 108.6 . . ? C26 C27 H27B 108.6 2_565 . ? C26 C27 H27B 108.6 . . ? H27A C27 H27B 107.5 . . ? O1S C1S C2S 121.0(15) . . ? O1S C1S C3S 119.3(16) . . ? C2S C1S C3S 119.8(15) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? C1S C3S H3S1 109.5 . . ? C1S C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? C1S C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 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 O12 Cu1 O11 C11 -7.4(7) 5_565 . . . ? O14 Cu1 O11 C11 -88.5(3) 4_464 . . . ? O13 Cu1 O11 C11 78.9(3) 8_656 . . . ? N21 Cu1 O11 C11 168.1(3) . . . . ? Cu1 Cu1 O11 C11 -0.3(3) 5_565 . . . ? O12 Cu1 N21 C21 159.3(3) 5_565 . . . ? O14 Cu1 N21 C21 -112.2(3) 4_464 . . . ? O13 Cu1 N21 C21 69.5(3) 8_656 . . . ? O11 Cu1 N21 C21 -19.7(3) . . . . ? Cu1 Cu1 N21 C21 92.7(5) 5_565 . . . ? O12 Cu1 N21 C25 -10.8(3) 5_565 . . . ? O14 Cu1 N21 C25 77.7(3) 4_464 . . . ? O13 Cu1 N21 C25 -100.6(3) 8_656 . . . ? O11 Cu1 N21 C25 170.2(3) . . . . ? Cu1 Cu1 N21 C25 -77.4(5) 5_565 . . . ? Cu1 O11 C11 O12 -2.2(5) . . . . ? Cu1 O11 C11 C12 175.2(3) . . . . ? Cu1 O12 C11 O11 4.5(6) 5_565 . . . ? Cu1 O12 C11 C12 -172.9(3) 5_565 . . . ? O11 C11 C12 C13 39.1(5) . . . . ? O12 C11 C12 C13 -143.3(4) . . . . ? C11 C12 C13 C14 -172.6(3) . . . . ? C12 C13 C14 C15 59.7(5) . . . . ? Cu1 O13 C15 O14 10.7(5) 8_655 . . . ? Cu1 O13 C15 C14 -169.1(2) 8_655 . . . ? Cu1 O14 C15 O13 -8.8(5) 4_564 . . . ? Cu1 O14 C15 C14 171.1(2) 4_564 . . . ? C13 C14 C15 O13 32.2(5) . . . . ? C13 C14 C15 O14 -147.7(3) . . . . ? C25 N21 C21 C22 -0.5(6) . . . . ? Cu1 N21 C21 C22 -171.0(3) . . . . ? N21 C21 C22 C23 0.1(7) . . . . ? C21 C22 C23 C24 0.3(6) . . . . ? C21 C22 C23 C26 -176.8(4) . . . . ? C22 C23 C24 C25 -0.4(6) . . . . ? C26 C23 C24 C25 176.8(4) . . . . ? C21 N21 C25 C24 0.4(6) . . . . ? Cu1 N21 C25 C24 171.1(4) . . . . ? C23 C24 C25 N21 0.1(7) . . . . ? C22 C23 C26 C27 96.2(4) . . . . ? C24 C23 C26 C27 -80.9(5) . . . . ? C23 C26 C27 C26 178.1(4) . . . 2_565 ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.842 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.095