# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Bao-Hui Ye' _publ_contact_author_name 'Bao-Hui Ye' _publ_contact_author_address ; Xingang Xilu 135 Guangzhou Guangzhou Guangdong China 510275 ; _publ_contact_author_email cesybh@mail.sysu.edu.cn data_1 _database_code_depnum_ccdc_archive 'CCDC 819470' #TrackingRef '- complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu4 N10 O13' _chemical_formula_weight 1042.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9590(5) _cell_length_b 10.0093(5) _cell_length_c 11.8264(6) _cell_angle_alpha 94.8230(10) _cell_angle_beta 110.5320(10) _cell_angle_gamma 118.4430(10) _cell_volume 924.49(8) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3598 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate-like _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.873 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 2.353 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4529 _exptl_absorpt_correction_T_max 0.6505 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_% negligible _diffrn_reflns_number 7732 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3598 _reflns_number_gt 3333 _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. ; _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^)+(0.0416P)^2^+0.4484P] 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 3598 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0693 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 Cu1 Cu 0.23751(3) 1.09861(3) 0.31835(2) 0.01932(8) Uani 1 1 d . . . Cu2 Cu 0.56490(3) 1.20962(3) 0.28799(2) 0.02218(9) Uani 1 1 d . . . O6 O 0.22444(18) 1.22731(18) 0.20228(14) 0.0297(3) Uani 1 1 d . . . N4 N 0.2862(2) 0.85671(19) 0.60185(15) 0.0196(3) Uani 1 1 d . . . O3 O 0.42614(17) 1.00142(17) 0.14285(13) 0.0254(3) Uani 1 1 d . . . O5 O 0.4639(2) 1.3070(2) 0.18104(15) 0.0329(4) Uani 1 1 d . . . C14 C 0.2765(2) 0.8942(2) 0.12109(18) 0.0210(4) Uani 1 1 d . . . O2 O 0.47938(16) 1.23935(16) 0.40899(12) 0.0208(3) Uani 1 1 d . . . H2B H 0.5144 1.2195 0.4781 0.031 Uiso 1 1 d R . . O1 O 0.49026(16) 1.08894(16) 0.59497(13) 0.0249(3) Uani 1 1 d . . . O4 O 0.19069(17) 0.90532(17) 0.17259(13) 0.0258(3) Uani 1 1 d . . . N1 N -0.0164(2) 0.9854(2) 0.25731(15) 0.0213(3) Uani 1 1 d . . . N5 N 0.2002(2) 0.63008(19) 0.70935(15) 0.0206(3) Uani 1 1 d . . . N2 N 0.2132(2) 0.98045(19) 0.44965(15) 0.0188(3) Uani 1 1 d . . . N3 N -0.0009(2) 0.78258(19) 0.49352(15) 0.0211(3) Uani 1 1 d . . . C13 C 0.1648(3) 0.5157(2) 0.76574(18) 0.0236(4) Uani 1 1 d . . . H13A H 0.2537 0.5021 0.8143 0.028 Uiso 1 1 calc R . . C1 C -0.1261(3) 0.9967(3) 0.15976(19) 0.0270(4) Uani 1 1 d . . . H1A H -0.0842 1.0610 0.1106 0.032 Uiso 1 1 calc R . . C16 C 0.3268(3) 1.2994(2) 0.1579(2) 0.0252(4) Uani 1 1 d . . . C8 C 0.1220(2) 0.7701(2) 0.57464(17) 0.0192(4) Uani 1 1 d . . . C6 C 0.0529(2) 0.8837(2) 0.42909(17) 0.0186(4) Uani 1 1 d . . . C9 C 0.0723(2) 0.6459(2) 0.63848(17) 0.0202(4) Uani 1 1 d . . . C7 C 0.3397(2) 0.9825(2) 0.55154(17) 0.0191(4) Uani 1 1 d . . . C2 C -0.2987(3) 0.9177(3) 0.1279(2) 0.0287(4) Uani 1 1 d . . . H2A H -0.3733 0.9303 0.0598 0.034 Uiso 1 1 calc R . . C4 C -0.2492(2) 0.8023(2) 0.29541(19) 0.0231(4) Uani 1 1 d . . . H4A H -0.2895 0.7328 0.3420 0.028 Uiso 1 1 calc R . . C15 C 0.1950(3) 0.7386(3) 0.0211(2) 0.0311(5) Uani 1 1 d . . . H15C H 0.1756 0.6530 0.0604 0.037 Uiso 1 1 calc R . . H15A H 0.2709 0.7492 -0.0173 0.037 Uiso 1 1 calc R . . H15B H 0.0858 0.7130 -0.0446 0.037 Uiso 1 1 calc R . . C5 C -0.0781(2) 0.8887(2) 0.32318(17) 0.0197(4) Uani 1 1 d . . . C11 C -0.1268(3) 0.4347(2) 0.68492(19) 0.0276(4) Uani 1 1 d . . . H11A H -0.2384 0.3682 0.6775 0.033 Uiso 1 1 calc R . . C3 C -0.3601(3) 0.8206(3) 0.1971(2) 0.0269(4) Uani 1 1 d . . . H3A H -0.4776 0.7665 0.1776 0.032 Uiso 1 1 calc R . . C17 C 0.2785(3) 1.3828(3) 0.0663(2) 0.0365(5) Uani 1 1 d . . . H17A H 0.2633 1.4603 0.1073 0.044 Uiso 1 1 calc R . . H17B H 0.1716 1.3041 -0.0086 0.044 Uiso 1 1 calc R . . H17C H 0.3691 1.4383 0.0404 0.044 Uiso 1 1 calc R . . C10 C -0.0922(3) 0.5521(2) 0.62435(19) 0.0255(4) Uani 1 1 d . . . H10A H -0.1792 0.5673 0.5747 0.031 Uiso 1 1 calc R . . C12 C 0.0031(3) 0.4164(2) 0.75578(19) 0.0262(4) Uani 1 1 d . . . H12A H -0.0180 0.3365 0.7973 0.031 Uiso 1 1 calc R . . O7 O 0.4573(5) 1.4437(4) 0.5713(4) 0.0486(10) Uani 0.50 1 d P . . H7B H 0.4769 1.3996 0.5200 0.073 Uiso 0.50 1 d PR . . H7C H 0.4945 1.5425 0.5858 0.073 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01909(13) 0.02133(14) 0.01995(13) 0.01043(10) 0.00912(10) 0.01170(10) Cu2 0.02458(14) 0.02884(15) 0.02153(14) 0.01453(11) 0.01182(11) 0.01817(11) O6 0.0272(7) 0.0327(8) 0.0360(8) 0.0221(7) 0.0155(7) 0.0182(7) N4 0.0207(7) 0.0198(8) 0.0178(7) 0.0068(6) 0.0078(6) 0.0109(6) O3 0.0219(7) 0.0291(8) 0.0197(7) 0.0063(6) 0.0074(6) 0.0116(6) O5 0.0357(8) 0.0473(10) 0.0367(8) 0.0294(8) 0.0218(7) 0.0305(8) C14 0.0233(9) 0.0217(10) 0.0180(9) 0.0085(7) 0.0063(7) 0.0139(8) O2 0.0214(6) 0.0212(7) 0.0183(6) 0.0074(5) 0.0090(5) 0.0102(5) O1 0.0190(7) 0.0250(7) 0.0229(7) 0.0101(6) 0.0063(6) 0.0081(6) O4 0.0258(7) 0.0238(7) 0.0265(7) 0.0050(6) 0.0137(6) 0.0116(6) N1 0.0228(8) 0.0256(9) 0.0210(8) 0.0102(7) 0.0113(7) 0.0154(7) N5 0.0235(8) 0.0191(8) 0.0186(8) 0.0070(6) 0.0094(7) 0.0109(7) N2 0.0200(7) 0.0194(8) 0.0182(7) 0.0071(6) 0.0084(6) 0.0114(6) N3 0.0199(8) 0.0220(8) 0.0212(8) 0.0084(7) 0.0096(7) 0.0107(7) C13 0.0308(10) 0.0210(10) 0.0213(9) 0.0098(8) 0.0119(8) 0.0149(8) C1 0.0290(10) 0.0368(12) 0.0233(10) 0.0164(9) 0.0125(9) 0.0216(9) C16 0.0275(10) 0.0234(10) 0.0281(10) 0.0124(8) 0.0125(9) 0.0154(8) C8 0.0220(9) 0.0181(9) 0.0163(8) 0.0043(7) 0.0082(7) 0.0103(8) C6 0.0215(9) 0.0197(9) 0.0176(9) 0.0056(7) 0.0095(7) 0.0127(8) C9 0.0223(9) 0.0190(9) 0.0163(9) 0.0047(7) 0.0082(7) 0.0096(8) C7 0.0215(9) 0.0204(9) 0.0172(9) 0.0066(7) 0.0096(7) 0.0119(8) C2 0.0274(10) 0.0396(12) 0.0255(10) 0.0146(9) 0.0104(9) 0.0228(10) C4 0.0239(9) 0.0261(10) 0.0225(9) 0.0091(8) 0.0111(8) 0.0151(8) C15 0.0308(11) 0.0285(11) 0.0298(11) 0.0025(9) 0.0098(9) 0.0167(9) C5 0.0233(9) 0.0218(9) 0.0182(9) 0.0061(7) 0.0100(8) 0.0145(8) C11 0.0243(10) 0.0230(10) 0.0243(10) 0.0051(8) 0.0109(8) 0.0053(8) C3 0.0215(9) 0.0320(11) 0.0273(10) 0.0078(9) 0.0097(8) 0.0157(9) C17 0.0351(12) 0.0433(14) 0.0455(14) 0.0319(12) 0.0208(11) 0.0264(11) C10 0.0228(9) 0.0266(10) 0.0206(9) 0.0077(8) 0.0077(8) 0.0102(8) C12 0.0336(11) 0.0185(10) 0.0218(10) 0.0073(8) 0.0130(9) 0.0102(8) O7 0.071(2) 0.0270(17) 0.065(2) 0.0144(17) 0.050(2) 0.0255(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.9075(13) . ? Cu1 O6 1.9729(14) . ? Cu1 N1 2.0132(16) . ? Cu1 N2 2.0416(16) . ? Cu1 O4 2.2245(14) . ? Cu2 O5 1.9517(15) . ? Cu2 O2 1.9714(13) . ? Cu2 N4 2.0161(16) 2_676 ? Cu2 O3 2.0470(14) . ? Cu2 N5 2.1004(16) 2_676 ? O6 C16 1.254(3) . ? N4 C8 1.328(2) . ? N4 C7 1.390(2) . ? N4 Cu2 2.0161(16) 2_676 ? O3 C14 1.265(2) . ? O5 C16 1.258(3) . ? C14 O4 1.248(2) . ? C14 C15 1.515(3) . ? O1 C7 1.222(2) . ? N1 C1 1.338(3) . ? N1 C5 1.348(3) . ? N5 C13 1.337(3) . ? N5 C9 1.348(3) . ? N5 Cu2 2.1004(16) 2_676 ? N2 C6 1.327(2) . ? N2 C7 1.395(2) . ? N3 C8 1.333(3) . ? N3 C6 1.339(2) . ? C13 C12 1.385(3) . ? C1 C2 1.386(3) . ? C16 C17 1.508(3) . ? C8 C9 1.481(3) . ? C6 C5 1.483(3) . ? C9 C10 1.382(3) . ? C2 C3 1.381(3) . ? C4 C5 1.384(3) . ? C4 C3 1.390(3) . ? C11 C12 1.379(3) . ? C11 C10 1.394(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O6 91.61(6) . . ? O2 Cu1 N1 165.45(6) . . ? O6 Cu1 N1 89.44(6) . . ? O2 Cu1 N2 95.35(6) . . ? O6 Cu1 N2 165.46(6) . . ? N1 Cu1 N2 80.65(6) . . ? O2 Cu1 O4 105.78(5) . . ? O6 Cu1 O4 93.12(6) . . ? N1 Cu1 O4 88.65(6) . . ? N2 Cu1 O4 97.24(6) . . ? O5 Cu2 O2 91.26(6) . . ? O5 Cu2 N4 168.23(7) . 2_676 ? O2 Cu2 N4 95.53(6) . 2_676 ? O5 Cu2 O3 91.81(7) . . ? O2 Cu2 O3 120.93(6) . . ? N4 Cu2 O3 92.92(6) 2_676 . ? O5 Cu2 N5 89.00(7) . 2_676 ? O2 Cu2 N5 127.29(6) . 2_676 ? N4 Cu2 N5 79.23(6) 2_676 2_676 ? O3 Cu2 N5 111.73(6) . 2_676 ? C16 O6 Cu1 128.58(14) . . ? C8 N4 C7 117.83(16) . . ? C8 N4 Cu2 116.18(13) . 2_676 ? C7 N4 Cu2 125.98(12) . 2_676 ? C14 O3 Cu2 120.90(13) . . ? C16 O5 Cu2 129.29(14) . . ? O4 C14 O3 126.48(18) . . ? O4 C14 C15 117.75(18) . . ? O3 C14 C15 115.76(18) . . ? Cu1 O2 Cu2 104.69(6) . . ? C14 O4 Cu1 134.07(13) . . ? C1 N1 C5 118.43(17) . . ? C1 N1 Cu1 126.70(14) . . ? C5 N1 Cu1 114.86(13) . . ? C13 N5 C9 118.30(17) . . ? C13 N5 Cu2 127.91(14) . 2_676 ? C9 N5 Cu2 113.77(13) . 2_676 ? C6 N2 C7 117.23(16) . . ? C6 N2 Cu1 113.80(13) . . ? C7 N2 Cu1 128.88(12) . . ? C8 N3 C6 113.22(16) . . ? N5 C13 C12 122.26(19) . . ? N1 C1 C2 122.28(19) . . ? O6 C16 O5 126.49(19) . . ? O6 C16 C17 116.46(18) . . ? O5 C16 C17 117.04(18) . . ? N4 C8 N3 125.92(18) . . ? N4 C8 C9 116.27(17) . . ? N3 C8 C9 117.78(17) . . ? N2 C6 N3 126.45(17) . . ? N2 C6 C5 116.00(17) . . ? N3 C6 C5 117.55(16) . . ? N5 C9 C10 122.92(18) . . ? N5 C9 C8 114.31(17) . . ? C10 C9 C8 122.75(18) . . ? O1 C7 N4 121.25(17) . . ? O1 C7 N2 122.11(17) . . ? N4 C7 N2 116.63(16) . . ? C3 C2 C1 118.75(19) . . ? C5 C4 C3 117.82(19) . . ? N1 C5 C4 122.91(18) . . ? N1 C5 C6 114.46(16) . . ? C4 C5 C6 122.63(18) . . ? C12 C11 C10 119.07(19) . . ? C2 C3 C4 119.73(19) . . ? C9 C10 C11 118.2(2) . . ? C11 C12 C13 119.26(19) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.326 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.076 # Attachment '- complex 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 819471' #TrackingRef '- complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H37 Cu4 N10 O15.50' _chemical_formula_weight 1087.90 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 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 7.5589(5) _cell_length_b 13.8920(8) _cell_length_c 18.9818(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.2330(10) _cell_angle_gamma 90.00 _cell_volume 1977.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3889 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 26.00 _exptl_crystal_description block _exptl_crystal_colour green-blue _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1102 _exptl_absorpt_coefficient_mu 2.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8789 _exptl_absorpt_correction_T_max 0.8976 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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_% negligible _diffrn_reflns_number 11834 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3889 _reflns_number_gt 3084 _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. ; _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^)+(0.0440P)^2^+0.6752P] 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 3889 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.64705(5) -0.17145(3) 0.13822(2) 0.02045(12) Uani 1 1 d . . . Cu2 Cu 0.62851(5) -0.07225(3) 0.28507(2) 0.02103(13) Uani 1 1 d . . . O2 O 0.7145(3) -0.18070(16) 0.23712(11) 0.0216(5) Uani 1 1 d . . . H2B H 0.6809 -0.2356 0.2501 0.032 Uiso 1 1 d R . . O4 O 0.3636(3) -0.11615(18) 0.15633(13) 0.0301(6) Uani 1 1 d . . . O3 O 0.3776(3) -0.12322(18) 0.27414(13) 0.0304(6) Uani 1 1 d . . . O6 O 0.7982(3) -0.05695(17) 0.13175(12) 0.0277(6) Uani 1 1 d . . . O1 O 0.4207(3) 0.13289(17) 0.26252(11) 0.0276(6) Uani 1 1 d . . . C1 C 0.3828(4) 0.4023(2) 0.51214(17) 0.0244(8) Uani 1 1 d . . . H1A H 0.3167 0.4569 0.4939 0.029 Uiso 1 1 calc R . . N1 N 0.4153(4) 0.33074(19) 0.46734(14) 0.0215(6) Uani 1 1 d . . . N4 N 0.5725(3) 0.03939(19) 0.34782(14) 0.0210(6) Uani 1 1 d . . . O5 O 0.7920(3) 0.01533(17) 0.23701(13) 0.0329(6) Uani 1 1 d . . . N3 N 0.6222(4) 0.0987(2) 0.46613(14) 0.0229(6) Uani 1 1 d . . . C8 C 0.6387(4) 0.0331(2) 0.41613(17) 0.0201(7) Uani 1 1 d . . . C6 C 0.5306(4) 0.1767(2) 0.44207(17) 0.0197(7) Uani 1 1 d . . . N5 N 0.7698(4) -0.1136(2) 0.38494(15) 0.0245(6) Uani 1 1 d . . . C10 C 0.8216(5) -0.0681(2) 0.50723(19) 0.0263(8) Uani 1 1 d . . . H10A H 0.8031 -0.0238 0.5437 0.032 Uiso 1 1 calc R . . C5 C 0.5070(4) 0.2532(2) 0.49474(17) 0.0216(7) Uani 1 1 d . . . N2 N 0.4589(4) 0.19296(19) 0.37562(13) 0.0195(6) Uani 1 1 d . . . C2 C 0.4437(5) 0.3978(3) 0.58420(18) 0.0280(8) Uani 1 1 d . . . H2A H 0.4211 0.4494 0.6147 0.034 Uiso 1 1 calc R . . C3 C 0.5372(5) 0.3180(3) 0.61102(18) 0.0274(8) Uani 1 1 d . . . H3A H 0.5783 0.3136 0.6603 0.033 Uiso 1 1 calc R . . C4 C 0.5709(5) 0.2442(2) 0.56528(17) 0.0248(8) Uani 1 1 d . . . H4A H 0.6364 0.1888 0.5824 0.030 Uiso 1 1 calc R . . C9 C 0.7472(4) -0.0531(2) 0.43800(17) 0.0214(7) Uani 1 1 d . . . C7 C 0.4797(4) 0.1223(2) 0.32475(17) 0.0206(7) Uani 1 1 d . . . C17 C 0.9869(5) 0.0763(3) 0.1607(2) 0.0367(10) Uani 1 1 d . . . H17A H 0.9659 0.0925 0.1101 0.044 Uiso 1 1 calc R . . H17B H 1.1053 0.0472 0.1717 0.044 Uiso 1 1 calc R . . H17C H 0.9804 0.1349 0.1890 0.044 Uiso 1 1 calc R . . C11 C 0.9241(5) -0.1500(3) 0.5219(2) 0.0313(9) Uani 1 1 d . . . H11A H 0.9767 -0.1630 0.5690 0.038 Uiso 1 1 calc R . . C13 C 0.8710(5) -0.1916(3) 0.4000(2) 0.0314(9) Uani 1 1 d . . . H13A H 0.8898 -0.2344 0.3625 0.038 Uiso 1 1 calc R . . C12 C 0.9494(5) -0.2122(3) 0.4680(2) 0.0332(9) Uani 1 1 d . . . H12A H 1.0196 -0.2685 0.4772 0.040 Uiso 1 1 calc R . . C16 C 0.8478(4) 0.0064(2) 0.17812(18) 0.0254(8) Uani 1 1 d . . . C14 C 0.3055(5) -0.1429(3) 0.2118(2) 0.0276(8) Uani 1 1 d . . . C15 C 0.1419(5) -0.2064(3) 0.2065(2) 0.0384(10) Uani 1 1 d . . . H15A H 0.0733 -0.1916 0.2456 0.046 Uiso 1 1 calc R . . H15B H 0.1784 -0.2741 0.2092 0.046 Uiso 1 1 calc R . . H15C H 0.0678 -0.1946 0.1611 0.046 Uiso 1 1 calc R . . O1W O 0.1193(4) 0.9125(2) 0.03384(15) 0.0512(8) Uani 1 1 d . . . H1WA H 0.1934 0.9046 0.0709 0.077 Uiso 1 1 d R . . H1WB H 0.0155 0.9210 0.0456 0.077 Uiso 1 1 d R . . O2W O 0.8718(5) 0.0030(4) 0.65901(19) 0.0653(14) Uani 0.75 1 d P . . H2WA H 0.9743 0.0137 0.6816 0.098 Uiso 0.75 1 d PR . . H2WB H 0.8063 0.0333 0.6848 0.098 Uiso 0.75 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0250(2) 0.0147(2) 0.0216(2) -0.00043(16) 0.00289(17) -0.00284(16) Cu2 0.0252(2) 0.0144(2) 0.0237(2) -0.00278(16) 0.00373(17) 0.00046(17) O2 0.0261(13) 0.0154(12) 0.0233(12) -0.0014(9) 0.0027(10) 0.0009(9) O4 0.0244(13) 0.0294(15) 0.0372(14) 0.0073(12) 0.0061(11) 0.0029(11) O3 0.0267(14) 0.0304(15) 0.0357(14) -0.0077(12) 0.0098(11) -0.0045(11) O6 0.0341(14) 0.0235(14) 0.0254(13) -0.0009(11) 0.0036(11) -0.0100(11) O1 0.0409(15) 0.0217(14) 0.0190(12) -0.0009(10) 0.0000(11) 0.0073(11) C1 0.0290(19) 0.0164(18) 0.0286(18) -0.0006(14) 0.0067(15) -0.0007(14) N1 0.0236(15) 0.0167(15) 0.0243(15) -0.0013(12) 0.0035(12) -0.0007(12) N4 0.0247(15) 0.0151(15) 0.0231(14) -0.0007(11) 0.0032(12) 0.0016(11) O5 0.0399(15) 0.0214(14) 0.0402(15) -0.0078(11) 0.0163(12) -0.0096(11) N3 0.0290(16) 0.0168(15) 0.0226(14) -0.0013(12) 0.0022(12) 0.0021(12) C8 0.0207(17) 0.0148(17) 0.0251(18) 0.0026(14) 0.0035(14) -0.0012(13) C6 0.0244(18) 0.0138(17) 0.0213(16) 0.0001(13) 0.0042(14) -0.0025(13) N5 0.0264(16) 0.0169(16) 0.0301(16) -0.0013(12) 0.0031(12) 0.0023(12) C10 0.0281(19) 0.0191(19) 0.0307(19) 0.0011(15) 0.0003(15) -0.0035(15) C5 0.0243(18) 0.0190(18) 0.0219(16) 0.0015(14) 0.0042(13) 0.0003(14) N2 0.0245(15) 0.0144(15) 0.0195(14) 0.0003(11) 0.0031(12) 0.0003(11) C2 0.036(2) 0.0194(19) 0.0295(19) -0.0089(15) 0.0078(16) -0.0029(16) C3 0.033(2) 0.029(2) 0.0196(17) -0.0018(15) 0.0026(15) -0.0035(16) C4 0.031(2) 0.0185(19) 0.0250(17) 0.0007(14) 0.0056(15) -0.0006(15) C9 0.0218(18) 0.0152(18) 0.0269(18) 0.0030(14) 0.0016(14) 0.0006(13) C7 0.0254(18) 0.0144(17) 0.0227(17) 0.0027(14) 0.0061(14) 0.0008(14) C17 0.045(2) 0.027(2) 0.041(2) -0.0070(17) 0.0146(19) -0.0170(18) C11 0.031(2) 0.028(2) 0.033(2) 0.0103(16) -0.0033(16) 0.0021(16) C13 0.034(2) 0.020(2) 0.041(2) -0.0035(16) 0.0059(17) 0.0080(16) C12 0.029(2) 0.021(2) 0.049(2) 0.0069(17) 0.0026(18) 0.0066(16) C16 0.0278(19) 0.0159(19) 0.032(2) -0.0008(15) 0.0036(15) -0.0005(14) C14 0.0208(18) 0.0191(19) 0.043(2) -0.0009(16) 0.0056(16) 0.0045(14) C15 0.030(2) 0.037(2) 0.047(2) 0.0031(19) 0.0012(18) -0.0086(18) O1W 0.062(2) 0.0380(18) 0.0479(18) -0.0015(14) -0.0133(15) -0.0163(15) O2W 0.048(3) 0.116(4) 0.033(2) -0.028(2) 0.0063(18) -0.014(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 O2 1.887(2) . ? Cu1 O6 1.971(2) . ? Cu1 N1 2.000(3) 2_645 ? Cu1 N2 2.051(3) 2_645 ? Cu1 O4 2.342(2) . ? Cu2 O2 1.916(2) . ? Cu2 O3 2.011(2) . ? Cu2 O5 2.031(2) . ? Cu2 N4 2.032(3) . ? Cu2 N5 2.134(3) . ? O4 C14 1.247(4) . ? O3 C14 1.269(4) . ? O6 C16 1.267(4) . ? O1 C7 1.218(4) . ? C1 N1 1.350(4) . ? C1 C2 1.388(5) . ? N1 C5 1.350(4) . ? N1 Cu1 2.000(3) 2_655 ? N4 C8 1.333(4) . ? N4 C7 1.390(4) . ? O5 C16 1.250(4) . ? N3 C8 1.333(4) . ? N3 C6 1.336(4) . ? C8 C9 1.481(4) . ? C6 N2 1.328(4) . ? C6 C5 1.485(4) . ? N5 C13 1.336(4) . ? N5 C9 1.339(4) . ? C10 C9 1.378(5) . ? C10 C11 1.385(5) . ? C5 C4 1.371(5) . ? N2 C7 1.400(4) . ? N2 Cu1 2.051(3) 2_655 ? C2 C3 1.378(5) . ? C3 C4 1.388(5) . ? C17 C16 1.498(5) . ? C11 C12 1.371(5) . ? C13 C12 1.381(5) . ? C14 C15 1.512(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O6 91.77(10) . . ? O2 Cu1 N1 176.34(10) . 2_645 ? O6 Cu1 N1 89.46(10) . 2_645 ? O2 Cu1 N2 96.73(10) . 2_645 ? O6 Cu1 N2 162.41(10) . 2_645 ? N1 Cu1 N2 81.18(10) 2_645 2_645 ? O2 Cu1 O4 90.78(9) . . ? O6 Cu1 O4 107.02(9) . . ? N1 Cu1 O4 92.16(10) 2_645 . ? N2 Cu1 O4 88.29(10) 2_645 . ? O2 Cu2 O3 92.63(10) . . ? O2 Cu2 O5 89.75(9) . . ? O3 Cu2 O5 141.64(11) . . ? O2 Cu2 N4 170.69(10) . . ? O3 Cu2 N4 93.78(10) . . ? O5 Cu2 N4 89.40(10) . . ? O2 Cu2 N5 92.78(10) . . ? O3 Cu2 N5 110.91(10) . . ? O5 Cu2 N5 107.20(11) . . ? N4 Cu2 N5 78.63(11) . . ? Cu1 O2 Cu2 110.74(11) . . ? C14 O4 Cu1 116.9(2) . . ? C14 O3 Cu2 117.4(2) . . ? C16 O6 Cu1 129.8(2) . . ? N1 C1 C2 121.6(3) . . ? C5 N1 C1 118.0(3) . . ? C5 N1 Cu1 114.8(2) . 2_655 ? C1 N1 Cu1 127.1(2) . 2_655 ? C8 N4 C7 118.3(3) . . ? C8 N4 Cu2 116.1(2) . . ? C7 N4 Cu2 125.6(2) . . ? C16 O5 Cu2 129.5(2) . . ? C8 N3 C6 113.7(3) . . ? N4 C8 N3 126.2(3) . . ? N4 C8 C9 116.9(3) . . ? N3 C8 C9 116.8(3) . . ? N2 C6 N3 126.5(3) . . ? N2 C6 C5 116.6(3) . . ? N3 C6 C5 116.9(3) . . ? C13 N5 C9 118.2(3) . . ? C13 N5 Cu2 128.1(2) . . ? C9 N5 Cu2 113.7(2) . . ? C9 C10 C11 117.8(3) . . ? N1 C5 C4 123.4(3) . . ? N1 C5 C6 114.3(3) . . ? C4 C5 C6 122.3(3) . . ? C6 N2 C7 117.9(3) . . ? C6 N2 Cu1 112.6(2) . 2_655 ? C7 N2 Cu1 129.2(2) . 2_655 ? C3 C2 C1 119.4(3) . . ? C2 C3 C4 119.3(3) . . ? C5 C4 C3 118.3(3) . . ? N5 C9 C10 123.1(3) . . ? N5 C9 C8 114.5(3) . . ? C10 C9 C8 122.3(3) . . ? O1 C7 N4 121.0(3) . . ? O1 C7 N2 121.7(3) . . ? N4 C7 N2 117.4(3) . . ? C12 C11 C10 119.6(3) . . ? N5 C13 C12 122.3(3) . . ? C11 C12 C13 119.0(3) . . ? O5 C16 O6 125.9(3) . . ? O5 C16 C17 117.2(3) . . ? O6 C16 C17 116.8(3) . . ? O4 C14 O3 124.6(3) . . ? O4 C14 C15 119.3(3) . . ? O3 C14 C15 116.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.491 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.092