# Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Hegen Zheng' _publ_contact_author_email ZHENGHG@NJU.EDU.CN _publ_section_title ; Syntheses, structures, photoluminescence and magnetic properties of five Compounds with 1,3,5-benzenetricarboxylate acid and imidazole ligands ; loop_ _publ_author_name 'Hegen Zheng' 'Jiao Xu' 'Stuart Batten' 'Zi-Jian Guo' 'Yi-Zhi Li' 'Zhao-Rui Pan' 'Tianwei Wang' # Attachment '1.cif' data_yy _database_code_depnum_ccdc_archive 'CCDC 742383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 N4 O7 Zn' _chemical_formula_weight 529.80 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8282(13) _cell_length_b 16.447(3) _cell_length_c 16.779(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.137(3) _cell_angle_gamma 90.00 _cell_volume 2151.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.885 _exptl_absorpt_process_details ? _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 11417 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0970 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4217 _reflns_number_gt 2775 _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^)+(0.0285P)^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 4217 _refine_ls_number_parameters 313 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.007 _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 C1 C 0.1555(6) 0.8606(2) 1.0570(2) 0.0257(10) Uani 1 1 d . . . C2 C 0.1910(6) 0.8201(3) 0.9879(2) 0.0306(11) Uani 1 1 d . . . H2 H 0.2948 0.7929 0.9865 0.037 Uiso 1 1 calc R . . C3 C 0.0726(6) 0.8195(2) 0.9203(2) 0.0266(10) Uani 1 1 d . . . C4 C -0.0790(5) 0.8611(2) 0.9228(2) 0.0292(11) Uani 1 1 d . . . H4 H -0.1576 0.8618 0.8778 0.035 Uiso 1 1 calc RD . . C5 C -0.1168(6) 0.9023(2) 0.9914(2) 0.0250(10) Uani 1 1 d . . . C6 C 0.0030(6) 0.9019(2) 1.0577(2) 0.0268(10) Uani 1 1 d . . . H6 H -0.0204 0.9302 1.1035 0.032 Uiso 1 1 calc R . . C7 C 0.1109(7) 0.7698(3) 0.8487(3) 0.0333(12) Uani 1 1 d . . . C8 C -0.2824(6) 0.9444(3) 0.9933(3) 0.0322(11) Uani 1 1 d . . . C9 C 0.2837(6) 0.8582(3) 1.1302(3) 0.0301(11) Uani 1 1 d . . . C10 C 0.9298(6) 0.7226(3) 1.1809(3) 0.0328(11) Uani 1 1 d . . . H10 H 0.9854 0.7310 1.2315 0.039 Uiso 1 1 calc R . . C11 C 0.9952(6) 0.6819(3) 1.1214(3) 0.0390(12) Uani 1 1 d . . . H11 H 1.1025 0.6573 1.1231 0.047 Uiso 1 1 calc R . . C12 C 0.7411(6) 0.7258(2) 1.0812(3) 0.0311(11) Uani 1 1 d . . . H12 H 0.6417 0.7367 1.0483 0.037 Uiso 1 1 calc R . . C13 C 0.8860(6) 0.6475(3) 0.9785(3) 0.0392(12) Uani 1 1 d . . . H13A H 1.0062 0.6391 0.9710 0.047 Uiso 1 1 calc R . . H13B H 0.8408 0.6861 0.9382 0.047 Uiso 1 1 calc R . . C14 C 0.7925(6) 0.5679(3) 0.9648(3) 0.0289(11) Uani 1 1 d . . . C15 C 0.7704(6) 0.5124(3) 1.0245(3) 0.0371(12) Uani 1 1 d . . . H15 H 0.8123 0.5242 1.0768 0.045 Uiso 1 1 calc R . . C16 C 0.6881(6) 0.4402(3) 1.0081(3) 0.0391(13) Uani 1 1 d . . . H16 H 0.6736 0.4035 1.0491 0.047 Uiso 1 1 calc R . . C17 C 0.6265(6) 0.4223(3) 0.9304(3) 0.0348(12) Uani 1 1 d . . . H17 H 0.5711 0.3731 0.9191 0.042 Uiso 1 1 calc R . . C18 C 0.6465(6) 0.4767(3) 0.8693(3) 0.0291(11) Uani 1 1 d . . . C19 C 0.7308(6) 0.5488(3) 0.8871(3) 0.0319(11) Uani 1 1 d . . . H19 H 0.7467 0.5854 0.8462 0.038 Uiso 1 1 calc R . . C20 C 0.5746(6) 0.4595(3) 0.7839(3) 0.0341(12) Uani 1 1 d . . . H30A H 0.6498 0.4832 0.7473 0.041 Uiso 1 1 calc R . . H30B H 0.5723 0.4012 0.7752 0.041 Uiso 1 1 calc R . . C21 C 0.3602(6) 0.5704(3) 0.7609(2) 0.0341(12) Uani 1 1 d . . . H58 H 0.4392 0.6126 0.7678 0.041 Uiso 1 1 calc R . . C22 C 0.2533(6) 0.4502(3) 0.7529(3) 0.0385(12) Uani 1 1 d . . . H59 H 0.2417 0.3939 0.7527 0.046 Uiso 1 1 calc R . . C23 C 0.1265(6) 0.5045(3) 0.7401(3) 0.0348(12) Uani 1 1 d . . . H60 H 0.0108 0.4919 0.7297 0.042 Uiso 1 1 calc R . . N1 N 0.7677(4) 0.7503(2) 1.1557(2) 0.0261(8) Uani 1 1 d . . . N2 N 0.8734(5) 0.6836(2) 1.0581(2) 0.0344(9) Uani 1 1 d . . . N3 N 0.4011(5) 0.4922(2) 0.76625(19) 0.0291(9) Uani 1 1 d . . . N4 N 0.1928(5) 0.5810(2) 0.7446(2) 0.0305(9) Uani 1 1 d . . . O1 O 0.4178(4) 0.81661(19) 1.12195(16) 0.0389(8) Uani 1 1 d . . . O2 O 0.2530(4) 0.89457(19) 1.19056(17) 0.0459(9) Uani 1 1 d . . . O3 O 0.2532(4) 0.7368(2) 0.84704(18) 0.0509(10) Uani 1 1 d . . . O4 O -0.0070(4) 0.76224(18) 0.79242(17) 0.0395(8) Uani 1 1 d . . . O5 O -0.3957(4) 0.9406(2) 0.93691(19) 0.0507(10) Uani 1 1 d . . . O6 O -0.3014(4) 0.98434(19) 1.05823(18) 0.0480(9) Uani 1 1 d D . . H6A H -0.3997 1.0067 1.0544 0.072 Uiso 1 1 d RD . . O7 O 0.56823(7) 0.75974(3) 0.89866(3) 0.207(3) Uani 1 1 d . . . H7D H 0.4639 0.7515 0.8820 0.248 Uiso 1 1 d R . . H7B H 0.6023 0.8039 0.8790 0.310 Uiso 1 1 d R . . Zn1 Zn 0.58903(7) 0.81157(3) 1.21380(3) 0.02788(16) Uani 1 1 d 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 C1 0.027(3) 0.028(2) 0.023(2) 0.0007(19) 0.003(2) -0.001(2) C2 0.031(3) 0.035(3) 0.026(2) 0.002(2) 0.005(2) 0.005(2) C3 0.032(3) 0.023(2) 0.025(2) -0.0005(19) 0.004(2) 0.000(2) C4 0.029(3) 0.035(3) 0.023(2) 0.004(2) -0.003(2) 0.000(2) C5 0.026(3) 0.025(2) 0.024(2) 0.0011(19) 0.002(2) 0.002(2) C6 0.032(3) 0.028(2) 0.021(2) -0.0044(19) 0.007(2) 0.001(2) C7 0.043(3) 0.028(3) 0.029(3) 0.002(2) 0.006(3) -0.002(3) C8 0.037(3) 0.036(3) 0.024(3) 0.000(2) 0.009(2) 0.006(2) C9 0.027(3) 0.033(3) 0.029(3) 0.002(2) 0.000(2) -0.001(2) C10 0.027(3) 0.037(3) 0.033(3) -0.002(2) -0.001(2) -0.005(2) C11 0.029(3) 0.040(3) 0.047(3) -0.001(3) -0.001(2) 0.003(3) C12 0.024(3) 0.030(3) 0.039(3) -0.001(2) 0.005(2) -0.001(2) C13 0.038(3) 0.042(3) 0.040(3) -0.007(2) 0.012(2) 0.000(3) C14 0.027(3) 0.027(3) 0.034(3) -0.002(2) 0.011(2) 0.003(2) C15 0.036(3) 0.046(3) 0.030(3) -0.005(2) 0.005(2) 0.005(3) C16 0.040(3) 0.040(3) 0.038(3) 0.009(2) 0.007(3) 0.006(3) C17 0.025(3) 0.032(3) 0.049(3) 0.003(2) 0.008(2) -0.002(2) C18 0.023(3) 0.029(3) 0.036(3) 0.000(2) 0.007(2) 0.006(2) C19 0.036(3) 0.028(3) 0.034(3) 0.004(2) 0.011(2) 0.003(2) C20 0.038(3) 0.027(3) 0.037(3) -0.002(2) 0.002(2) 0.001(2) C21 0.038(3) 0.023(3) 0.040(3) -0.001(2) -0.002(2) -0.005(2) C22 0.044(3) 0.028(3) 0.045(3) 0.003(2) 0.007(3) -0.011(3) C23 0.031(3) 0.036(3) 0.038(3) 0.001(2) 0.004(2) -0.007(2) N1 0.025(2) 0.027(2) 0.026(2) -0.0039(16) 0.0015(17) 0.0014(18) N2 0.031(2) 0.037(2) 0.036(2) -0.0078(19) 0.0055(19) -0.001(2) N3 0.033(2) 0.024(2) 0.029(2) 0.0029(16) 0.0002(19) -0.0027(19) N4 0.037(3) 0.024(2) 0.030(2) -0.0013(17) -0.0006(19) -0.0018(19) O1 0.0308(19) 0.056(2) 0.0282(17) -0.0026(16) -0.0062(15) 0.0122(18) O2 0.047(2) 0.063(2) 0.0270(18) -0.0175(17) -0.0040(17) 0.0147(19) O3 0.046(2) 0.065(2) 0.042(2) -0.0198(18) 0.0001(18) 0.019(2) O4 0.043(2) 0.049(2) 0.0259(17) -0.0108(15) -0.0044(16) 0.0057(18) O5 0.039(2) 0.073(3) 0.038(2) -0.0125(18) -0.0087(18) 0.021(2) O6 0.039(2) 0.065(2) 0.040(2) -0.0074(18) 0.0010(17) 0.0234(19) O7 0.136(6) 0.274(8) 0.205(7) 0.003(6) -0.016(5) -0.024(6) Zn1 0.0293(3) 0.0305(3) 0.0236(3) 0.0010(2) 0.0010(2) 0.0001(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 C1 C6 1.375(5) . ? C1 C2 1.386(5) . ? C1 C9 1.516(6) . ? C2 C3 1.398(5) . ? C2 H2 0.9300 . ? C3 C4 1.374(5) . ? C3 C7 1.505(6) . ? C4 C5 1.390(5) . ? C4 H4 0.9300 . ? C5 C6 1.390(5) . ? C5 C8 1.473(6) . ? C6 H6 0.9300 . ? C7 O3 1.242(5) . ? C7 O4 1.267(5) . ? C8 O5 1.239(5) . ? C8 O6 1.293(5) . ? C9 O2 1.218(5) . ? C9 O1 1.271(5) . ? C10 C11 1.341(6) . ? C10 N1 1.378(5) . ? C10 H10 0.9300 . ? C11 N2 1.363(5) . ? C11 H11 0.9300 . ? C12 N1 1.312(5) . ? C12 N2 1.332(5) . ? C12 H12 0.9300 . ? C13 N2 1.474(5) . ? C13 C14 1.508(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.378(6) . ? C14 C19 1.384(5) . ? C15 C16 1.366(6) . ? C15 H15 0.9300 . ? C16 C17 1.382(6) . ? C16 H16 0.9300 . ? C17 C18 1.380(6) . ? C17 H17 0.9300 . ? C18 C19 1.377(6) . ? C18 C20 1.518(6) . ? C19 H19 0.9300 . ? C20 N3 1.467(5) . ? C20 H30A 0.9700 . ? C20 H30B 0.9700 . ? C21 N3 1.326(5) . ? C21 N4 1.326(5) . ? C21 H58 0.9300 . ? C22 C23 1.339(6) . ? C22 N3 1.349(5) . ? C22 H59 0.9300 . ? C23 N4 1.361(5) . ? C23 H60 0.9300 . ? N1 Zn1 2.041(3) . ? N4 Zn1 1.993(3) 4_575 ? O1 Zn1 1.952(3) . ? O4 Zn1 1.989(3) 4_575 ? O6 H6A 0.8501 . ? O7 H7D 0.8501 . ? O7 H7B 0.8500 . ? Zn1 O4 1.989(3) 4_676 ? Zn1 N4 1.993(4) 4_676 ? 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 C6 C1 C2 119.0(4) . . ? C6 C1 C9 121.2(4) . . ? C2 C1 C9 119.9(4) . . ? C1 C2 C3 120.9(4) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 118.9(4) . . ? C4 C3 C7 121.9(4) . . ? C2 C3 C7 119.1(4) . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 118.9(4) . . ? C6 C5 C8 121.2(4) . . ? C4 C5 C8 120.0(4) . . ? C1 C6 C5 121.3(4) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? O3 C7 O4 122.4(4) . . ? O3 C7 C3 119.9(4) . . ? O4 C7 C3 117.7(4) . . ? O5 C8 O6 122.8(4) . . ? O5 C8 C5 122.1(4) . . ? O6 C8 C5 115.1(4) . . ? O2 C9 O1 125.6(4) . . ? O2 C9 C1 119.7(4) . . ? O1 C9 C1 114.7(4) . . ? C11 C10 N1 109.9(4) . . ? C11 C10 H10 125.1 . . ? N1 C10 H10 125.1 . . ? C10 C11 N2 106.4(4) . . ? C10 C11 H11 126.8 . . ? N2 C11 H11 126.8 . . ? N1 C12 N2 112.1(4) . . ? N1 C12 H12 124.0 . . ? N2 C12 H12 124.0 . . ? N2 C13 C14 114.6(4) . . ? N2 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? N2 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C19 118.5(4) . . ? C15 C14 C13 123.8(4) . . ? C19 C14 C13 117.7(4) . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 119.6(4) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 120.6(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 118.7(4) . . ? C19 C18 C20 119.7(4) . . ? C17 C18 C20 121.5(4) . . ? C18 C19 C14 121.4(4) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? N3 C20 C18 112.3(4) . . ? N3 C20 H30A 109.1 . . ? C18 C20 H30A 109.1 . . ? N3 C20 H30B 109.1 . . ? C18 C20 H30B 109.1 . . ? H30A C20 H30B 107.9 . . ? N3 C21 N4 111.7(4) . . ? N3 C21 H58 124.1 . . ? N4 C21 H58 124.1 . . ? C23 C22 N3 107.3(4) . . ? C23 C22 H59 126.3 . . ? N3 C22 H59 126.3 . . ? C22 C23 N4 109.5(4) . . ? C22 C23 H60 125.2 . . ? N4 C23 H60 125.2 . . ? C12 N1 C10 104.7(4) . . ? C12 N1 Zn1 123.4(3) . . ? C10 N1 Zn1 131.9(3) . . ? C12 N2 C11 107.0(4) . . ? C12 N2 C13 126.2(4) . . ? C11 N2 C13 126.8(4) . . ? C21 N3 C22 106.7(4) . . ? C21 N3 C20 125.7(4) . . ? C22 N3 C20 127.6(4) . . ? C21 N4 C23 104.7(4) . . ? C21 N4 Zn1 122.9(3) . 4_575 ? C23 N4 Zn1 131.3(3) . 4_575 ? C9 O1 Zn1 116.9(3) . . ? C7 O4 Zn1 105.1(3) . 4_575 ? C8 O6 H6A 109.1 . . ? H7D O7 H7B 109.5 . . ? O1 Zn1 O4 106.01(13) . 4_676 ? O1 Zn1 N4 113.73(14) . 4_676 ? O4 Zn1 N4 122.56(13) 4_676 4_676 ? O1 Zn1 N1 95.47(13) . . ? O4 Zn1 N1 109.33(13) 4_676 . ? N4 Zn1 N1 106.33(15) 4_676 . ? 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 O7 H7D O3 0.85 1.72 2.568(3) 178.8 . O6 H6A O5 0.85 1.84 2.681(5) 170.8 3_477 O7 H7B O5 0.85 2.45 3.050(3) 128.4 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.749 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.079 # Attachment '2.cif' data_80927bm _database_code_depnum_ccdc_archive 'CCDC 742384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 N6 O10 Zn2' _chemical_formula_weight 684.21 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' Zn Zn 0.2839 1.4301 '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 10.666(2) _cell_length_b 16.748(3) _cell_length_c 14.201(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.299(4) _cell_angle_gamma 90.00 _cell_volume 2525.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block ' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1388 _exptl_absorpt_coefficient_mu 1.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6 _exptl_absorpt_correction_T_max 0.8 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 13481 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4933 _reflns_number_gt 3419 _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^)+(0.0807P)^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 4933 _refine_ls_number_parameters 370 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C1 C 0.9659(5) 0.2299(3) 0.6563(4) 0.0237(12) Uani 1 1 d . . . C2 C 1.0779(5) 0.1896(3) 0.6796(4) 0.0266(13) Uani 1 1 d . . . H2 H 1.0768 0.1343 0.6856 0.032 Uiso 1 1 calc R . . C3 C 1.1899(5) 0.2294(3) 0.6941(4) 0.0235(12) Uani 1 1 d . . . C4 C 1.1921(5) 0.3103(3) 0.6881(4) 0.0283(13) Uani 1 1 d . . . H4 H 1.2683 0.3373 0.6991 0.034 Uiso 1 1 calc R . . C5 C 1.0804(5) 0.3538(3) 0.6653(4) 0.0260(13) Uani 1 1 d . . . C6 C 0.9683(5) 0.3126(3) 0.6492(4) 0.0258(13) Uani 1 1 d . . . H6 H 0.8938 0.3404 0.6336 0.031 Uiso 1 1 calc R . . C7 C 0.8437(6) 0.1865(3) 0.6415(4) 0.0293(13) Uani 1 1 d . . . C8 C 1.0830(6) 0.4433(3) 0.6655(4) 0.0321(14) Uani 1 1 d . . . C9 C 0.9611(5) 0.6552(3) 0.6018(4) 0.0284(13) Uani 1 1 d . . . H9 H 0.9208 0.6062 0.6057 0.034 Uiso 1 1 calc R . . C10 C 0.9938(5) 0.7830(3) 0.5792(4) 0.0316(14) Uani 1 1 d . . . H10 H 0.9821 0.8369 0.5652 0.038 Uiso 1 1 calc RD . . C11 C 1.1031(6) 0.7476(3) 0.6061(4) 0.0342(14) Uani 1 1 d . . . H11 H 1.1809 0.7730 0.6143 0.041 Uiso 1 1 calc R . . C12 C 0.7150(5) 0.8087(3) 0.5723(4) 0.0260(13) Uani 1 1 d . . . H12 H 0.7640 0.8515 0.5955 0.031 Uiso 1 1 calc R . . C13 C 0.7698(5) 0.7361(3) 0.5553(4) 0.0238(12) Uani 1 1 d . . . C14 C 0.6965(5) 0.6720(3) 0.5194(4) 0.0263(13) Uani 1 1 d . . . H14 H 0.7332 0.6228 0.5092 0.032 Uiso 1 1 calc R . . C15 C 0.5689(5) 0.6830(3) 0.4995(4) 0.0250(12) Uani 1 1 d . . . C16 C 0.5119(5) 0.7537(3) 0.5178(4) 0.0261(13) Uani 1 1 d . . . H16 H 0.4252 0.7596 0.5060 0.031 Uiso 1 1 calc R . . C17 C 0.5863(5) 0.8166(3) 0.5543(4) 0.0238(12) Uani 1 1 d . . . C18 C 0.5379(5) 0.5600(3) 0.4039(4) 0.0256(12) Uani 1 1 d . . . H18 H 0.6222 0.5532 0.3938 0.031 Uiso 1 1 calc R . . C19 C 0.3394(6) 0.5437(3) 0.3998(4) 0.0323(14) Uani 1 1 d . . . H19 H 0.2590 0.5230 0.3855 0.039 Uiso 1 1 calc R . . C20 C 0.3676(5) 0.6085(3) 0.4544(4) 0.0311(14) Uani 1 1 d . . . H20 H 0.3114 0.6398 0.4847 0.037 Uiso 1 1 calc R . . C21 C 0.4119(6) 0.9165(3) 0.5382(4) 0.0329(14) Uani 1 1 d . . . H21 H 0.3606 0.8937 0.4889 0.039 Uiso 1 1 calc R . . C22 C 0.3889(6) 0.9829(3) 0.5859(4) 0.0354(15) Uani 1 1 d . . . H22 H 0.3175 1.0146 0.5743 0.043 Uiso 1 1 calc R . . C23 C 0.5666(6) 0.9396(3) 0.6466(4) 0.0301(13) Uani 1 1 d . . . H23 H 0.6420 0.9342 0.6846 0.036 Uiso 1 1 calc R . . C24 C 1.3112(6) 0.1868(4) 0.7188(4) 0.0376(16) Uani 1 1 d . . . N1 N 1.0825(4) 0.6664(3) 0.6202(3) 0.0290(11) Uani 1 1 d . . . N2 N 0.9014(4) 0.7254(3) 0.5760(3) 0.0245(10) Uani 1 1 d . . . N3 N 0.4948(4) 0.6192(3) 0.4564(3) 0.0237(10) Uani 1 1 d . . . N4 N 0.4475(4) 0.5132(3) 0.3689(3) 0.0279(11) Uani 1 1 d . . . N5 N 0.5266(4) 0.8887(3) 0.5766(3) 0.0262(11) Uani 1 1 d . . . N6 N 0.4854(4) 0.9980(3) 0.6544(3) 0.0306(11) Uani 1 1 d . . . O1 O 0.8421(4) 0.1129(2) 0.6710(3) 0.0318(10) Uani 1 1 d . . . O2 O 0.7507(4) 0.2202(3) 0.6028(4) 0.0511(13) Uani 1 1 d . . . O3 O 1.3044(4) 0.1141(2) 0.7446(3) 0.0430(11) Uani 1 1 d . . . O4 O 1.4116(5) 0.2219(3) 0.7146(4) 0.0708(17) Uani 1 1 d . . . O5 O 0.9830(4) 0.4816(3) 0.6549(4) 0.0606(15) Uani 1 1 d . . . O6 O 1.1924(4) 0.4760(2) 0.6779(3) 0.0381(11) Uani 1 1 d . . . O7 O 1.3699(3) 0.6228(2) 0.6875(3) 0.0305(9) Uani 1 1 d . . . O8 O 0.3708(4) 0.8002(2) 0.7375(3) 0.0762(17) Uani 1 1 d . . . H8A H 0.4150 0.7859 0.7876 0.114 Uiso 1 1 d R . . H8C H 0.3772 0.7655 0.6946 0.114 Uiso 1 1 d R . . O9 O 0.9013(4) 0.9769(2) 0.5658(3) 0.138(4) Uani 1 1 d R . . H9A H 0.9413 1.0089 0.6041 0.207 Uiso 1 1 d RD . . H9C H 0.8947 0.9971 0.5106 0.207 Uiso 1 1 d R . . O10 O 0.1538(7) 0.9368(3) 0.6855(5) 0.138 Uani 1 1 d . . . H10A H 0.0944 0.9277 0.6427 0.207 Uiso 1 1 d R . . H10C H 0.1335 0.9754 0.7197 0.207 Uiso 1 1 d R . . Zn1 Zn 1.19736(6) 0.59110(4) 0.69710(5) 0.0283(2) Uani 1 1 d . . . Zn2 Zn 1.52572(6) 0.56977(4) 0.73184(5) 0.0252(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.028(3) 0.017(3) 0.025(3) 0.000(2) -0.001(2) 0.001(2) C2 0.031(3) 0.017(3) 0.031(3) 0.002(2) 0.002(3) 0.007(2) C3 0.023(3) 0.023(3) 0.024(3) 0.000(2) 0.002(2) 0.006(2) C4 0.020(3) 0.035(3) 0.030(3) 0.001(3) 0.000(2) -0.002(2) C5 0.027(3) 0.020(3) 0.030(3) 0.003(2) -0.001(3) 0.003(2) C6 0.018(3) 0.022(3) 0.036(3) 0.002(2) -0.003(2) 0.005(2) C7 0.029(3) 0.025(3) 0.034(3) -0.002(3) 0.004(3) -0.001(2) C8 0.034(4) 0.017(3) 0.045(4) -0.001(3) 0.004(3) -0.002(2) C9 0.026(3) 0.025(3) 0.032(3) 0.000(2) -0.005(3) 0.003(2) C10 0.028(3) 0.023(3) 0.043(4) 0.005(3) -0.001(3) -0.003(2) C11 0.026(3) 0.035(4) 0.042(4) 0.002(3) -0.001(3) -0.003(3) C12 0.028(3) 0.021(3) 0.028(3) -0.002(2) 0.001(3) 0.000(2) C13 0.021(3) 0.024(3) 0.026(3) 0.003(2) -0.002(2) 0.003(2) C14 0.028(3) 0.021(3) 0.029(3) -0.004(2) 0.001(3) 0.005(2) C15 0.026(3) 0.024(3) 0.025(3) 0.001(2) -0.002(2) 0.000(2) C16 0.023(3) 0.027(3) 0.027(3) -0.001(2) -0.005(2) 0.002(2) C17 0.028(3) 0.020(3) 0.024(3) -0.001(2) 0.003(2) 0.005(2) C18 0.022(3) 0.021(3) 0.033(3) -0.003(2) -0.003(3) 0.000(2) C19 0.025(3) 0.028(3) 0.043(4) 0.001(3) -0.001(3) -0.003(2) C20 0.025(3) 0.027(3) 0.040(4) -0.003(3) -0.001(3) 0.004(2) C21 0.026(3) 0.031(3) 0.040(4) -0.006(3) -0.007(3) 0.005(2) C22 0.030(4) 0.032(3) 0.043(4) -0.002(3) -0.005(3) 0.010(3) C23 0.032(3) 0.025(3) 0.032(3) -0.005(2) -0.004(3) 0.005(3) C24 0.031(4) 0.052(4) 0.028(3) 0.000(3) -0.002(3) 0.012(3) N1 0.026(3) 0.023(3) 0.036(3) -0.001(2) -0.004(2) 0.006(2) N2 0.023(3) 0.020(2) 0.029(3) -0.0029(19) -0.001(2) 0.0023(19) N3 0.022(3) 0.021(2) 0.028(3) 0.0003(19) -0.002(2) 0.0039(19) N4 0.030(3) 0.019(2) 0.034(3) 0.000(2) -0.001(2) 0.000(2) N5 0.025(3) 0.021(2) 0.032(3) -0.003(2) -0.006(2) 0.0026(19) N6 0.029(3) 0.025(3) 0.037(3) -0.004(2) -0.002(2) 0.008(2) O1 0.039(3) 0.019(2) 0.037(2) -0.0003(17) 0.006(2) -0.0059(17) O2 0.025(2) 0.037(3) 0.088(4) 0.014(2) -0.014(2) -0.0010(19) O3 0.036(3) 0.030(2) 0.061(3) 0.003(2) -0.007(2) 0.017(2) O4 0.025(3) 0.070(4) 0.117(5) 0.028(3) 0.001(3) 0.007(2) O5 0.030(3) 0.024(2) 0.126(5) 0.006(3) 0.000(3) 0.0039(19) O6 0.028(2) 0.018(2) 0.068(3) -0.005(2) 0.004(2) -0.0018(17) O7 0.019(2) 0.026(2) 0.046(2) -0.0016(18) -0.0020(19) -0.0020(16) O8 0.088(5) 0.066(4) 0.073(4) -0.007(3) -0.002(3) 0.000(3) O9 0.218(10) 0.041(4) 0.166(8) -0.018(4) 0.081(7) 0.005(5) O10 0.209 0.055 0.158 -0.018 0.055 0.001 Zn1 0.0210(4) 0.0204(4) 0.0423(4) -0.0024(3) -0.0032(3) 0.0017(3) Zn2 0.0228(4) 0.0204(4) 0.0317(4) -0.0001(3) -0.0014(3) -0.0050(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 C1 C2 1.385(7) . ? C1 C6 1.389(7) . ? C1 C7 1.491(8) . ? C2 C3 1.366(8) . ? C2 H2 0.9300 . ? C3 C4 1.358(7) . ? C3 C24 1.490(8) . ? C4 C5 1.409(7) . ? C4 H4 0.9300 . ? C5 C6 1.381(7) . ? C5 C8 1.498(7) . ? C6 H6 0.9300 . ? C7 O2 1.226(7) . ? C7 O1 1.302(6) . ? C8 O5 1.243(7) . ? C8 O6 1.286(7) . ? C9 N1 1.311(7) . ? C9 N2 1.370(7) . ? C9 H9 0.9300 . ? C10 C11 1.332(8) . ? C10 N2 1.377(7) . ? C10 H10 0.9300 . ? C11 N1 1.395(7) . ? C11 H11 0.9300 . ? C12 C13 1.379(7) . ? C12 C17 1.379(8) . ? C12 H12 0.9300 . ? C13 C14 1.396(7) . ? C13 N2 1.419(7) . ? C14 C15 1.377(8) . ? C14 H14 0.9300 . ? C15 C16 1.366(7) . ? C15 N3 1.433(7) . ? C16 C17 1.391(7) . ? C16 H16 0.9300 . ? C17 N5 1.414(6) . ? C18 N4 1.305(7) . ? C18 N3 1.347(7) . ? C18 H18 0.9300 . ? C19 C20 1.352(8) . ? C19 N4 1.369(7) . ? C19 H19 0.9300 . ? C20 N3 1.366(7) . ? C20 H20 0.9300 . ? C21 C22 1.337(8) . ? C21 N5 1.374(7) . ? C21 H21 0.9300 . ? C22 N6 1.373(7) . ? C22 H22 0.9300 . ? C23 N6 1.317(7) . ? C23 N5 1.349(7) . ? C23 H23 0.9300 . ? C24 O4 1.229(8) . ? C24 O3 1.275(7) . ? N1 Zn1 2.009(5) . ? N4 Zn2 2.033(4) 3_766 ? N6 Zn2 2.026(5) 2_756 ? O1 Zn1 1.992(4) 2_746 ? O3 Zn2 1.958(4) 2_846 ? O6 Zn1 1.946(4) . ? O7 Zn1 1.932(4) . ? O7 Zn2 1.938(4) . ? O8 H8A 0.8507 . ? O8 H8C 0.8494 . ? O9 H9A 0.8501 . ? O9 H9C 0.8500 . ? O10 H10A 0.8501 . ? O10 H10C 0.8500 . ? Zn1 O1 1.992(4) 2_756 ? Zn2 O3 1.958(4) 2_856 ? Zn2 N6 2.026(5) 2_746 ? Zn2 N4 2.033(4) 3_766 ? 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 C2 C1 C6 118.8(5) . . ? C2 C1 C7 121.3(5) . . ? C6 C1 C7 119.9(5) . . ? C3 C2 C1 121.4(5) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C4 C3 C2 119.8(5) . . ? C4 C3 C24 118.2(5) . . ? C2 C3 C24 122.0(5) . . ? C3 C4 C5 120.8(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 118.7(5) . . ? C6 C5 C8 121.1(5) . . ? C4 C5 C8 120.1(5) . . ? C5 C6 C1 120.5(5) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 O1 123.1(5) . . ? O2 C7 C1 119.9(5) . . ? O1 C7 C1 117.0(5) . . ? O5 C8 O6 123.6(5) . . ? O5 C8 C5 120.1(5) . . ? O6 C8 C5 116.3(5) . . ? N1 C9 N2 110.9(5) . . ? N1 C9 H9 124.6 . . ? N2 C9 H9 124.6 . . ? C11 C10 N2 107.6(5) . . ? C11 C10 H10 126.2 . . ? N2 C10 H10 126.2 . . ? C10 C11 N1 109.3(5) . . ? C10 C11 H11 125.4 . . ? N1 C11 H11 125.4 . . ? C13 C12 C17 118.9(5) . . ? C13 C12 H12 120.5 . . ? C17 C12 H12 120.5 . . ? C12 C13 C14 120.6(5) . . ? C12 C13 N2 120.2(5) . . ? C14 C13 N2 119.2(5) . . ? C15 C14 C13 118.8(5) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C16 C15 C14 121.7(5) . . ? C16 C15 N3 119.4(5) . . ? C14 C15 N3 118.9(5) . . ? C15 C16 C17 118.6(5) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C12 C17 C16 121.3(5) . . ? C12 C17 N5 120.1(5) . . ? C16 C17 N5 118.5(5) . . ? N4 C18 N3 112.0(5) . . ? N4 C18 H18 124.0 . . ? N3 C18 H18 124.0 . . ? C20 C19 N4 109.5(5) . . ? C20 C19 H19 125.2 . . ? N4 C19 H19 125.2 . . ? C19 C20 N3 106.5(5) . . ? C19 C20 H20 126.7 . . ? N3 C20 H20 126.7 . . ? C22 C21 N5 106.2(5) . . ? C22 C21 H21 126.9 . . ? N5 C21 H21 126.9 . . ? C21 C22 N6 110.5(5) . . ? C21 C22 H22 124.7 . . ? N6 C22 H22 124.7 . . ? N6 C23 N5 111.4(5) . . ? N6 C23 H23 124.3 . . ? N5 C23 H23 124.3 . . ? O4 C24 O3 122.9(6) . . ? O4 C24 C3 120.1(6) . . ? O3 C24 C3 117.0(6) . . ? C9 N1 C11 106.1(5) . . ? C9 N1 Zn1 124.1(4) . . ? C11 N1 Zn1 126.4(4) . . ? C9 N2 C10 106.2(5) . . ? C9 N2 C13 126.1(5) . . ? C10 N2 C13 127.6(5) . . ? C18 N3 C20 106.4(5) . . ? C18 N3 C15 125.7(5) . . ? C20 N3 C15 127.8(5) . . ? C18 N4 C19 105.6(5) . . ? C18 N4 Zn2 122.1(4) . 3_766 ? C19 N4 Zn2 131.1(4) . 3_766 ? C23 N5 C21 106.7(5) . . ? C23 N5 C17 125.9(5) . . ? C21 N5 C17 127.1(5) . . ? C23 N6 C22 105.1(5) . . ? C23 N6 Zn2 126.5(4) . 2_756 ? C22 N6 Zn2 125.3(4) . 2_756 ? C7 O1 Zn1 119.1(3) . 2_746 ? C24 O3 Zn2 109.6(4) . 2_846 ? C8 O6 Zn1 117.0(4) . . ? Zn1 O7 Zn2 130.2(2) . . ? H8A O8 H8C 109.5 . . ? H9A O9 H9C 109.5 . . ? H10A O10 H10C 109.5 . . ? O7 Zn1 O6 106.01(17) . . ? O7 Zn1 O1 107.54(17) . 2_756 ? O6 Zn1 O1 107.94(17) . 2_756 ? O7 Zn1 N1 109.04(18) . . ? O6 Zn1 N1 122.53(19) . . ? O1 Zn1 N1 103.02(17) 2_756 . ? O7 Zn2 O3 129.36(18) . 2_856 ? O7 Zn2 N6 114.79(18) . 2_746 ? O3 Zn2 N6 102.15(19) 2_856 2_746 ? O7 Zn2 N4 104.87(18) . 3_766 ? O3 Zn2 N4 101.04(19) 2_856 3_766 ? N6 Zn2 N4 100.21(18) 2_746 3_766 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.615 _refine_diff_density_min -2.500 _refine_diff_density_rms 0.134 # Attachment '3.cif' data_81007am _database_code_depnum_ccdc_archive 'CCDC 742385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H46 N8 O18 Zn3' _chemical_formula_weight 1291.10 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' Zn Zn 0.2839 1.4301 '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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1215(14) _cell_length_b 20.539(3) _cell_length_c 13.621(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.457(3) _cell_angle_gamma 90.00 _cell_volume 2509.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 1.512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 13404 _diffrn_reflns_av_R_equivalents 0.0725 _diffrn_reflns_av_sigmaI/netI 0.1354 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4934 _reflns_number_gt 2761 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0115P)^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 4934 _refine_ls_number_parameters 364 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 C1 C 0.1066(6) 0.3048(3) 0.6252(5) 0.0342(16) Uani 1 1 d . . . H16 H 0.1112 0.2888 0.5620 0.041 Uiso 1 1 calc R . . C2 C 0.0487(7) 0.3182(3) 0.7676(4) 0.0406(17) Uani 1 1 d . . . H17 H 0.0035 0.3127 0.8230 0.049 Uiso 1 1 calc R . . C3 C 0.1515(7) 0.3637(3) 0.7603(5) 0.0476(19) Uani 1 1 d . . . H34 H 0.1895 0.3947 0.8079 0.057 Uiso 1 1 calc R . . C4 C 0.2855(7) 0.3960(3) 0.6253(5) 0.0437(18) Uani 1 1 d . . . C5 C 0.3327(7) 0.4537(3) 0.6665(5) 0.0464(19) Uani 1 1 d . . . H10 H 0.3089 0.4664 0.7273 0.056 Uiso 1 1 calc R . . C6 C 0.4166(7) 0.4938(3) 0.6172(5) 0.0476(19) Uani 1 1 d . . . H13 H 0.4473 0.5337 0.6461 0.057 Uiso 1 1 calc R . . C7 C 0.4573(6) 0.4784(3) 0.5289(5) 0.0422(19) Uani 1 1 d . . . C8 C 0.4132(8) 0.4174(3) 0.4883(6) 0.067 Uani 1 1 d . . . H44 H 0.4420 0.4034 0.4297 0.081 Uiso 1 1 calc R . . C9 C 0.3232(8) 0.3774(4) 0.5387(6) 0.067 Uani 1 1 d . . . H12 H 0.2899 0.3374 0.5111 0.081 Uiso 1 1 calc R . . C10 C 0.1800(6) 0.0141(3) 0.3343(4) 0.0261(14) Uani 1 1 d . . . H8 H 0.1920 -0.0308 0.3306 0.031 Uiso 1 1 calc R . . C11 C 0.1174(7) 0.1075(3) 0.3771(5) 0.0400(17) Uani 1 1 d . . . H9 H 0.0767 0.1404 0.4106 0.048 Uiso 1 1 calc R . . C12 C 0.1906(7) 0.1177(3) 0.3027(5) 0.0398(17) Uani 1 1 d . . . H33 H 0.2096 0.1575 0.2750 0.048 Uiso 1 1 calc R . . C13 C 0.3129(6) 0.0417(3) 0.1969(4) 0.0265(14) Uani 1 1 d . . . C14 C 0.3023(6) 0.0810(3) 0.1156(4) 0.0289(15) Uani 1 1 d . . . H2 H 0.2454 0.1188 0.1118 0.035 Uiso 1 1 calc R . . C15 C 0.3755(6) 0.0651(3) 0.0390(4) 0.0305(15) Uani 1 1 d . . . H3 H 0.3675 0.0925 -0.0161 0.037 Uiso 1 1 calc R . . C16 C 0.4620(6) 0.0085(3) 0.0427(4) 0.0271(14) Uani 1 1 d . . . C17 C 0.4725(7) -0.0288(3) 0.1269(5) 0.0452(19) Uani 1 1 d . . . H5 H 0.5314 -0.0661 0.1325 0.054 Uiso 1 1 calc R . . C18 C 0.3990(7) -0.0133(3) 0.2039(4) 0.0433(18) Uani 1 1 d . . . H6 H 0.4079 -0.0399 0.2599 0.052 Uiso 1 1 calc R . . C19 C 0.1031(6) 0.1063(3) 0.6643(4) 0.0244(14) Uani 1 1 d . . . C20 C 0.2330(6) 0.1446(3) 0.7235(4) 0.0212(13) Uani 1 1 d U . . C21 C 0.2186(6) 0.1755(3) 0.8105(4) 0.0243(14) Uani 1 1 d . . . H23 H 0.1305 0.1712 0.8352 0.029 Uiso 1 1 calc R . . C22 C 0.3347(6) 0.2132(3) 0.8626(4) 0.0245(14) Uani 1 1 d . . . C23 C 0.4660(6) 0.2176(3) 0.8249(4) 0.0272(14) Uani 1 1 d . . . H21 H 0.5439 0.2428 0.8587 0.033 Uiso 1 1 calc R . . C24 C 0.4840(6) 0.1857(3) 0.7391(4) 0.0248(14) Uani 1 1 d . . . C25 C 0.3659(6) 0.1485(2) 0.6887(4) 0.0247(14) Uani 1 1 d U . . H19 H 0.3767 0.1260 0.6312 0.030 Uiso 1 1 calc R . . C26 C 0.3142(7) 0.2438(3) 0.9591(4) 0.0322(16) Uani 1 1 d . . . C27 C 0.6270(7) 0.1888(3) 0.7006(5) 0.0355(17) Uani 1 1 d . . . N1 N 0.0190(5) 0.2812(2) 0.6841(4) 0.0305(12) Uani 1 1 d . . . N2 N 0.1886(5) 0.3551(2) 0.6692(4) 0.0348(13) Uani 1 1 d . . . N3 N 0.1094(5) 0.0424(2) 0.3982(3) 0.0299(13) Uani 1 1 d . . . N4 N 0.2329(5) 0.0565(2) 0.2752(3) 0.0270(12) Uani 1 1 d . . . O1 O 0.1324(4) 0.06192(18) 0.6109(3) 0.0351(11) Uani 1 1 d . . . O2 O -0.0277(4) 0.12327(16) 0.6744(3) 0.0281(10) Uani 1 1 d . . . O3 O 0.6440(4) 0.1543(2) 0.6280(3) 0.0437(12) Uani 1 1 d . . . O4 O 0.7283(4) 0.22589(19) 0.7415(3) 0.0440(12) Uani 1 1 d . . . O5 O 0.2195(5) 0.22297(19) 1.0043(3) 0.0447(12) Uani 1 1 d . . . O6 O 0.4050(4) 0.28990(19) 0.9945(3) 0.0382(11) Uani 1 1 d . . . O7 O -0.1746(4) 0.07102(17) 0.4617(3) 0.0394(11) Uani 1 1 d . . . H7B H -0.2107 0.0800 0.5133 0.059 Uiso 1 1 d R . . H7C H -0.1383 0.1053 0.4406 0.059 Uiso 1 1 d R . . O8 O 0.5281(5) 0.0652(3) 0.4786(4) 0.097(2) Uani 1 1 d . . . H8A H 0.5630 0.0831 0.4315 0.145 Uiso 1 1 d R . . H8B H 0.5448 0.0895 0.5300 0.145 Uiso 1 1 d R . . O9 O 0.3807(14) 0.2363(6) 0.4661(10) 0.431(9) Uani 1 1 d . . . H9B H 0.3548 0.2345 0.4030 0.646 Uiso 1 1 d RD . . H9C H 0.4731 0.2276 0.4822 0.646 Uiso 1 1 d R . . Zn1 Zn -0.13108(7) 0.20856(3) 0.63974(5) 0.0296(2) Uani 1 1 d . . . Zn2 Zn 0.0000 0.0000 0.5000 0.0267(3) Uani 1 2 d S . . 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 C1 0.034(4) 0.029(4) 0.039(4) -0.003(3) 0.004(3) -0.003(3) C2 0.052(5) 0.042(4) 0.029(4) -0.002(3) 0.010(3) 0.010(4) C3 0.045(5) 0.047(5) 0.048(5) -0.017(4) 0.002(4) -0.014(4) C4 0.036(4) 0.053(5) 0.044(5) -0.009(4) 0.011(4) -0.007(4) C5 0.057(5) 0.038(4) 0.042(5) -0.004(4) 0.001(4) -0.012(4) C6 0.052(5) 0.030(4) 0.055(5) -0.007(4) -0.007(4) -0.013(4) C7 0.023(4) 0.037(5) 0.067(5) -0.010(4) 0.009(4) -0.005(3) C8 0.065 0.057 0.079 -0.029 0.009 -0.002 C9 0.065 0.057 0.079 -0.029 0.009 -0.002 C10 0.033(4) 0.018(4) 0.028(4) 0.007(3) 0.007(3) 0.000(3) C11 0.058(5) 0.025(4) 0.044(4) -0.005(3) 0.028(4) 0.000(3) C12 0.056(5) 0.022(4) 0.049(5) -0.001(3) 0.029(4) -0.004(3) C13 0.028(4) 0.023(4) 0.032(4) 0.003(3) 0.016(3) -0.004(3) C14 0.033(4) 0.022(4) 0.035(4) 0.002(3) 0.014(3) 0.001(3) C15 0.035(4) 0.027(4) 0.032(4) 0.010(3) 0.014(3) 0.004(3) C16 0.024(3) 0.030(4) 0.029(4) 0.000(3) 0.010(3) -0.002(3) C17 0.063(5) 0.034(4) 0.046(4) 0.016(3) 0.031(4) 0.029(4) C18 0.065(5) 0.042(5) 0.033(4) 0.021(3) 0.036(4) 0.017(4) C19 0.030(4) 0.022(4) 0.021(3) 0.004(3) 0.005(3) -0.005(3) C20 0.020(3) 0.021(3) 0.023(3) 0.004(3) 0.006(3) 0.000(3) C21 0.018(3) 0.025(3) 0.031(4) 0.003(3) 0.009(3) -0.002(3) C22 0.026(3) 0.023(3) 0.022(3) 0.003(3) -0.002(3) 0.001(3) C23 0.024(3) 0.026(4) 0.032(4) -0.003(3) 0.005(3) -0.005(3) C24 0.020(3) 0.025(4) 0.031(4) 0.001(3) 0.009(3) -0.003(3) C25 0.028(3) 0.021(3) 0.026(3) -0.001(3) 0.006(3) 0.009(3) C26 0.041(4) 0.025(4) 0.029(4) 0.004(3) 0.005(3) 0.009(3) C27 0.029(4) 0.029(4) 0.050(5) 0.015(3) 0.014(4) 0.011(3) N1 0.026(3) 0.026(3) 0.040(3) 0.004(3) 0.006(3) -0.002(2) N2 0.030(3) 0.038(3) 0.038(3) -0.001(3) 0.009(3) -0.005(3) N3 0.041(3) 0.026(3) 0.027(3) -0.005(2) 0.017(3) -0.005(3) N4 0.031(3) 0.021(3) 0.031(3) -0.002(2) 0.011(2) -0.001(2) O1 0.037(3) 0.036(3) 0.033(3) -0.019(2) 0.011(2) -0.001(2) O2 0.021(2) 0.019(2) 0.044(3) 0.0005(19) 0.005(2) -0.0002(18) O3 0.031(3) 0.057(3) 0.048(3) 0.001(3) 0.019(2) 0.004(2) O4 0.023(2) 0.038(3) 0.074(3) -0.004(2) 0.015(2) -0.010(2) O5 0.056(3) 0.044(3) 0.040(3) -0.008(2) 0.025(2) -0.005(2) O6 0.052(3) 0.033(3) 0.029(3) -0.006(2) 0.004(2) -0.004(2) O7 0.045(3) 0.031(3) 0.042(3) 0.000(2) 0.009(2) 0.003(2) O8 0.070(4) 0.149(6) 0.074(4) -0.020(4) 0.022(3) -0.035(4) O9 0.45(2) 0.42(2) 0.45(2) 0.023(18) 0.145(16) 0.003(16) Zn1 0.0269(4) 0.0309(4) 0.0332(4) -0.0008(4) 0.0113(3) 0.0006(4) Zn2 0.0267(6) 0.0301(6) 0.0255(6) -0.0004(5) 0.0108(4) -0.0016(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 C1 N1 1.322(6) . ? C1 N2 1.350(6) . ? C1 H16 0.9300 . ? C2 C3 1.340(8) . ? C2 N1 1.354(7) . ? C2 H17 0.9300 . ? C3 N2 1.357(7) . ? C3 H34 0.9300 . ? C4 C9 1.343(8) . ? C4 C5 1.349(8) . ? C4 N2 1.427(7) . ? C5 C6 1.378(8) . ? C5 H10 0.9300 . ? C6 C7 1.359(8) . ? C6 H13 0.9300 . ? C7 C8 1.398(8) . ? C7 C7 1.496(12) 3_666 ? C8 C9 1.424(9) . ? C8 H44 0.9300 . ? C9 H12 0.9300 . ? C10 N3 1.309(6) . ? C10 N4 1.335(6) . ? C10 H8 0.9300 . ? C11 C12 1.326(7) . ? C11 N3 1.373(6) . ? C11 H9 0.9300 . ? C12 N4 1.387(6) . ? C12 H33 0.9300 . ? C13 C14 1.359(7) . ? C13 C18 1.369(7) . ? C13 N4 1.430(6) . ? C14 C15 1.376(7) . ? C14 H2 0.9300 . ? C15 C16 1.401(7) . ? C15 H3 0.9300 . ? C16 C17 1.368(7) . ? C16 C16 1.499(10) 3_655 ? C17 C18 1.381(7) . ? C17 H5 0.9300 . ? C18 H6 0.9300 . ? C19 O1 1.225(6) . ? C19 O2 1.274(6) . ? C19 C20 1.526(7) . ? C20 C21 1.371(7) . ? C20 C25 1.382(7) . ? C21 C22 1.397(6) . ? C21 H23 0.9300 . ? C22 C23 1.389(7) . ? C22 C26 1.499(7) . ? C23 C24 1.375(7) . ? C23 H21 0.9300 . ? C24 C25 1.396(6) . ? C24 C27 1.493(7) . ? C25 H19 0.9300 . ? C26 O5 1.225(6) . ? C26 O6 1.293(6) . ? C27 O4 1.248(6) . ? C27 O3 1.249(7) . ? C27 Zn1 2.526(6) 1_655 ? N1 Zn1 2.042(5) . ? N3 Zn2 2.044(5) . ? O1 Zn2 2.167(4) . ? O2 Zn1 2.005(3) . ? O3 Zn1 2.315(4) 1_655 ? O4 Zn1 2.083(4) 1_655 ? O6 Zn1 2.063(4) 4_666 ? O7 Zn2 2.153(3) . ? O7 H7B 0.8499 . ? O7 H7C 0.8500 . ? O8 H8A 0.8500 . ? O8 H8B 0.8501 . ? O9 H9B 0.8500 . ? O9 H9C 0.8501 . ? Zn1 O6 2.063(4) 4_565 ? Zn1 O4 2.083(4) 1_455 ? Zn1 O3 2.315(4) 1_455 ? Zn1 C27 2.526(6) 1_455 ? Zn2 N3 2.044(5) 3_556 ? Zn2 O7 2.153(3) 3_556 ? Zn2 O1 2.167(4) 3_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 111.0(6) . . ? N1 C1 H16 124.5 . . ? N2 C1 H16 124.5 . . ? C3 C2 N1 111.4(6) . . ? C3 C2 H17 124.3 . . ? N1 C2 H17 124.3 . . ? C2 C3 N2 105.7(6) . . ? C2 C3 H34 127.2 . . ? N2 C3 H34 127.2 . . ? C9 C4 C5 120.1(7) . . ? C9 C4 N2 118.5(7) . . ? C5 C4 N2 121.3(6) . . ? C4 C5 C6 119.1(7) . . ? C4 C5 H10 120.5 . . ? C6 C5 H10 120.5 . . ? C7 C6 C5 123.9(6) . . ? C7 C6 H13 118.0 . . ? C5 C6 H13 118.0 . . ? C6 C7 C8 116.9(6) . . ? C6 C7 C7 125.5(8) . 3_666 ? C8 C7 C7 117.6(8) . 3_666 ? C7 C8 C9 118.5(7) . . ? C7 C8 H44 120.8 . . ? C9 C8 H44 120.8 . . ? C4 C9 C8 121.4(7) . . ? C4 C9 H12 119.3 . . ? C8 C9 H12 119.3 . . ? N3 C10 N4 112.7(5) . . ? N3 C10 H8 123.6 . . ? N4 C10 H8 123.6 . . ? C12 C11 N3 111.5(5) . . ? C12 C11 H9 124.2 . . ? N3 C11 H9 124.2 . . ? C11 C12 N4 105.5(5) . . ? C11 C12 H33 127.3 . . ? N4 C12 H33 127.3 . . ? C14 C13 C18 120.1(6) . . ? C14 C13 N4 120.7(5) . . ? C18 C13 N4 119.2(5) . . ? C13 C14 C15 120.3(6) . . ? C13 C14 H2 119.9 . . ? C15 C14 H2 119.9 . . ? C14 C15 C16 121.1(5) . . ? C14 C15 H3 119.4 . . ? C16 C15 H3 119.4 . . ? C17 C16 C15 116.6(5) . . ? C17 C16 C16 123.2(7) . 3_655 ? C15 C16 C16 120.1(6) . 3_655 ? C16 C17 C18 122.5(6) . . ? C16 C17 H5 118.7 . . ? C18 C17 H5 118.7 . . ? C13 C18 C17 119.3(6) . . ? C13 C18 H6 120.4 . . ? C17 C18 H6 120.4 . . ? O1 C19 O2 125.3(5) . . ? O1 C19 C20 117.8(5) . . ? O2 C19 C20 116.9(5) . . ? C21 C20 C25 119.8(5) . . ? C21 C20 C19 120.6(5) . . ? C25 C20 C19 119.6(5) . . ? C20 C21 C22 120.9(5) . . ? C20 C21 H23 119.6 . . ? C22 C21 H23 119.6 . . ? C23 C22 C21 118.2(5) . . ? C23 C22 C26 123.4(5) . . ? C21 C22 C26 118.3(5) . . ? C24 C23 C22 121.8(5) . . ? C24 C23 H21 119.1 . . ? C22 C23 H21 119.1 . . ? C23 C24 C25 118.5(5) . . ? C23 C24 C27 121.7(5) . . ? C25 C24 C27 119.7(5) . . ? C20 C25 C24 120.6(5) . . ? C20 C25 H19 119.7 . . ? C24 C25 H19 119.7 . . ? O5 C26 O6 122.0(6) . . ? O5 C26 C22 120.4(6) . . ? O6 C26 C22 117.5(6) . . ? O4 C27 O3 120.8(6) . . ? O4 C27 C24 119.4(6) . . ? O3 C27 C24 119.7(6) . . ? O4 C27 Zn1 55.2(3) . 1_655 ? O3 C27 Zn1 65.8(3) . 1_655 ? C24 C27 Zn1 173.1(5) . 1_655 ? C1 N1 C2 104.7(5) . . ? C1 N1 Zn1 122.4(4) . . ? C2 N1 Zn1 132.8(4) . . ? C1 N2 C3 107.2(5) . . ? C1 N2 C4 126.9(6) . . ? C3 N2 C4 125.6(6) . . ? C10 N3 C11 104.0(5) . . ? C10 N3 Zn2 128.4(4) . . ? C11 N3 Zn2 127.5(4) . . ? C10 N4 C12 106.2(5) . . ? C10 N4 C13 126.9(5) . . ? C12 N4 C13 126.8(5) . . ? C19 O1 Zn2 134.1(4) . . ? C19 O2 Zn1 128.6(4) . . ? C27 O3 Zn1 84.7(4) . 1_655 ? C27 O4 Zn1 95.3(4) . 1_655 ? C26 O6 Zn1 99.6(4) . 4_666 ? Zn2 O7 H7B 109.1 . . ? Zn2 O7 H7C 109.1 . . ? H7B O7 H7C 109.5 . . ? H8A O8 H8B 109.5 . . ? H9B O9 H9C 109.5 . . ? O2 Zn1 N1 107.91(16) . . ? O2 Zn1 O6 95.12(16) . 4_565 ? N1 Zn1 O6 93.27(18) . 4_565 ? O2 Zn1 O4 108.21(16) . 1_455 ? N1 Zn1 O4 98.00(18) . 1_455 ? O6 Zn1 O4 149.31(16) 4_565 1_455 ? O2 Zn1 O3 88.20(15) . 1_455 ? N1 Zn1 O3 155.66(17) . 1_455 ? O6 Zn1 O3 103.57(15) 4_565 1_455 ? O4 Zn1 O3 58.90(14) 1_455 1_455 ? O2 Zn1 C27 100.60(17) . 1_455 ? N1 Zn1 C27 126.8(2) . 1_455 ? O6 Zn1 C27 128.14(19) 4_565 1_455 ? O4 Zn1 C27 29.46(17) 1_455 1_455 ? O3 Zn1 C27 29.49(16) 1_455 1_455 ? N3 Zn2 N3 180.0 3_556 . ? N3 Zn2 O7 88.72(16) 3_556 3_556 ? N3 Zn2 O7 91.28(16) . 3_556 ? N3 Zn2 O7 91.28(16) 3_556 . ? N3 Zn2 O7 88.72(16) . . ? O7 Zn2 O7 180.0 3_556 . ? N3 Zn2 O1 93.21(16) 3_556 . ? N3 Zn2 O1 86.79(16) . . ? O7 Zn2 O1 86.24(14) 3_556 . ? O7 Zn2 O1 93.76(14) . . ? N3 Zn2 O1 86.79(16) 3_556 3_556 ? N3 Zn2 O1 93.21(16) . 3_556 ? O7 Zn2 O1 93.76(14) 3_556 3_556 ? O7 Zn2 O1 86.24(14) . 3_556 ? O1 Zn2 O1 180.00(16) . 3_556 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.011 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.095 # Attachment '4.cif' data_yy2 _database_code_depnum_ccdc_archive 'CCDC 742386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H44 N8 Ni3 O17' _chemical_formula_weight 1253.10 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0505(11) _cell_length_b 20.457(2) _cell_length_c 13.5723(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.210(2) _cell_angle_gamma 90.00 _cell_volume 2464.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 1.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13167 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4843 _reflns_number_gt 3476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0612P)^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 4843 _refine_ls_number_parameters 368 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1418 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.007 _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 C1 C 0.0937(5) 0.3920(2) 0.1621(3) 0.0166(10) Uani 1 1 d . . . C2 C 0.2262(5) 0.3555(2) 0.2195(3) 0.0163(10) Uani 1 1 d . . . C3 C 0.3593(5) 0.3513(2) 0.1834(3) 0.0180(10) Uani 1 1 d . . . H3 H 0.3676 0.3735 0.1249 0.022 Uiso 1 1 calc R . . C4 C 0.4803(5) 0.3147(2) 0.2331(3) 0.0192(11) Uani 1 1 d . . . C5 C 0.6238(6) 0.3104(2) 0.1936(4) 0.0214(11) Uani 1 1 d . . . C6 C 0.4661(5) 0.2814(2) 0.3208(3) 0.0196(11) Uani 1 1 d . . . H6 H 0.5449 0.2555 0.3537 0.023 Uiso 1 1 calc R . . C7 C 0.3355(5) 0.2868(2) 0.3589(3) 0.0170(10) Uani 1 1 d . . . C8 C 0.3243(6) 0.2538(2) 0.4561(3) 0.0192(11) Uani 1 1 d . . . C9 C 0.2156(5) 0.3239(2) 0.3081(3) 0.0181(10) Uani 1 1 d . . . H9 H 0.1279 0.3276 0.3339 0.022 Uiso 1 1 calc R . . C10 C 0.1072(6) 0.1986(2) 0.1182(4) 0.0279(12) Uani 1 1 d . . . H10 H 0.1137 0.2135 0.0544 0.033 Uiso 1 1 calc R . . C11 C 0.0432(6) 0.1874(2) 0.2602(4) 0.0271(12) Uani 1 1 d . . . H11 H -0.0038 0.1936 0.3146 0.032 Uiso 1 1 calc R . . C12 C 0.1473(7) 0.1426(3) 0.2555(4) 0.0360(14) Uani 1 1 d . . . H12 H 0.1844 0.1119 0.3048 0.043 Uiso 1 1 calc R . . C13 C 0.2879(6) 0.1082(3) 0.1216(4) 0.0293(13) Uani 1 1 d . . . C14 C 0.3349(7) 0.0495(3) 0.1645(4) 0.0376(14) Uani 1 1 d . . . H14 H 0.3107 0.0375 0.2255 0.045 Uiso 1 1 calc R . . C15 C 0.4184(7) 0.0082(3) 0.1166(4) 0.0396(15) Uani 1 1 d . . . H15 H 0.4501 -0.0314 0.1471 0.048 Uiso 1 1 calc R . . C16 C 0.4571(6) 0.0227(3) 0.0260(5) 0.0390(14) Uani 1 1 d U . . C17 C 0.4103(8) 0.0829(3) -0.0150(5) 0.0534(17) Uani 1 1 d U . . H17 H 0.4339 0.0950 -0.0762 0.064 Uiso 1 1 calc R . . C18 C 0.3293(7) 0.1254(3) 0.0333(5) 0.050 Uani 1 1 d U . . H18 H 0.3026 0.1663 0.0054 0.060 Uiso 1 1 calc R . . C19 C 0.1221(6) 0.3925(3) -0.1196(4) 0.0272(12) Uani 1 1 d U . . H19 H 0.0821 0.3596 -0.0855 0.033 Uiso 1 1 calc R . . C20 C 0.1956(6) 0.3826(2) -0.1951(4) 0.0302(13) Uani 1 1 d . . . H20 H 0.2142 0.3427 -0.2233 0.036 Uiso 1 1 calc R . . C21 C 0.1846(6) 0.4874(2) -0.1636(3) 0.0198(11) Uani 1 1 d . . . H21 H 0.1960 0.5324 -0.1674 0.024 Uiso 1 1 calc R . . C22 C 0.3164(6) 0.4592(2) -0.3010(4) 0.0218(11) Uani 1 1 d . . . C23 C 0.4035(6) 0.5137(3) -0.2949(4) 0.0328(13) Uani 1 1 d U . . H23 H 0.4148 0.5401 -0.2382 0.039 Uiso 1 1 calc R . . C24 C 0.4749(6) 0.5300(3) -0.3717(4) 0.0325(13) Uani 1 1 d U . . H24 H 0.5334 0.5677 -0.3664 0.039 Uiso 1 1 calc R . . C25 C 0.4618(6) 0.4910(2) -0.4583(3) 0.0237(12) Uani 1 1 d . . . C26 C 0.3760(6) 0.4347(2) -0.4606(4) 0.0249(12) Uani 1 1 d . . . H26 H 0.3675 0.4068 -0.5156 0.030 Uiso 1 1 calc R . . C27 C 0.3023(6) 0.4187(2) -0.3834(3) 0.0223(11) Uani 1 1 d . . . H27 H 0.2440 0.3810 -0.3871 0.027 Uiso 1 1 calc R . . N1 N 0.0149(4) 0.22316(18) 0.1733(3) 0.0215(9) Uani 1 1 d . . . N2 N 0.1899(5) 0.14971(19) 0.1654(3) 0.0258(10) Uani 1 1 d . . . N3 N 0.1144(5) 0.45768(19) -0.1000(3) 0.0217(10) Uani 1 1 d . . . N4 N 0.2379(5) 0.44383(19) -0.2225(3) 0.0220(9) Uani 1 1 d . . . Ni1 Ni 0.0000 0.5000 0.0000 0.0153(2) Uani 1 2 d S . . Ni2 Ni -0.14740(7) 0.29009(3) 0.12741(4) 0.01871(19) Uani 1 1 d . . . O1 O 0.1226(4) 0.43813(16) 0.1084(2) 0.0239(8) Uani 1 1 d . . . O2 O -0.0364(4) 0.37480(14) 0.1725(2) 0.0193(7) Uani 1 1 d . . . O3 O 0.6382(4) 0.34211(16) 0.1168(2) 0.0264(8) Uani 1 1 d . . . O4 O 0.7291(4) 0.27481(16) 0.2373(2) 0.0245(8) Uani 1 1 d . . . O5 O 0.4089(4) 0.20576(15) 0.4859(2) 0.0222(8) Uani 1 1 d . . . O6 O 0.2352(4) 0.27528(16) 0.5080(2) 0.0264(8) Uani 1 1 d . . . O7 O 0.1691(4) 0.56849(16) 0.0441(2) 0.0266(8) Uani 1 1 d D . . H7 H 0.1385 0.6048 0.0241 0.040 Uiso 1 1 calc R . . H7A H 0.2558 0.5597 0.0402 0.040 Uiso 1 1 d RD . . O8 O 0.5337(5) 0.4347(2) 0.9732(3) 0.0660(14) Uani 1 1 d . . . H8A H 0.5355 0.3936 0.9822 0.099 Uiso 1 1 d R . . H8B H 0.4601 0.4510 0.9953 0.099 Uiso 1 1 d R . . O9 O 0.8855(5) 0.2339(2) 0.4529(3) 0.248(11) Uani 0.50 1 d PR . . H9A H 0.8584 0.2504 0.3946 0.298 Uiso 0.50 1 d PR . . H9B H 0.9661 0.2524 0.4827 0.372 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 C1 0.023(3) 0.018(3) 0.010(2) -0.0042(19) 0.005(2) 0.002(2) C2 0.022(3) 0.013(2) 0.015(2) 0.0009(19) 0.005(2) 0.001(2) C3 0.023(3) 0.019(3) 0.013(2) 0.003(2) 0.007(2) -0.001(2) C4 0.021(3) 0.019(3) 0.021(3) -0.001(2) 0.013(2) -0.001(2) C5 0.023(3) 0.021(3) 0.022(3) -0.001(2) 0.008(2) -0.002(2) C6 0.016(3) 0.024(3) 0.018(3) 0.002(2) 0.004(2) 0.006(2) C7 0.018(3) 0.017(3) 0.017(2) 0.000(2) 0.006(2) -0.003(2) C8 0.023(3) 0.017(3) 0.019(3) -0.002(2) 0.009(2) -0.002(2) C9 0.016(3) 0.021(3) 0.018(2) -0.003(2) 0.007(2) -0.001(2) C10 0.030(3) 0.028(3) 0.027(3) 0.000(2) 0.008(2) 0.002(2) C11 0.030(3) 0.028(3) 0.025(3) 0.000(2) 0.008(2) 0.006(2) C12 0.046(4) 0.035(3) 0.026(3) 0.011(3) 0.004(3) 0.011(3) C13 0.021(3) 0.029(3) 0.038(3) 0.000(3) 0.004(2) 0.007(2) C14 0.042(4) 0.035(3) 0.034(3) -0.004(3) 0.002(3) 0.010(3) C15 0.047(4) 0.029(3) 0.042(4) 0.001(3) 0.006(3) 0.019(3) C16 0.022(3) 0.036(3) 0.062(4) -0.009(3) 0.016(3) 0.002(2) C17 0.0540(19) 0.0528(18) 0.0547(19) 0.0020(10) 0.0136(10) 0.0026(10) C18 0.050 0.050 0.051 0.001 0.014 0.002 C19 0.0281(15) 0.0270(15) 0.0276(15) 0.0008(10) 0.0081(10) 0.0000(10) C20 0.047(4) 0.015(3) 0.036(3) 0.000(2) 0.026(3) 0.001(2) C21 0.028(3) 0.015(3) 0.018(2) -0.001(2) 0.008(2) 0.000(2) C22 0.029(3) 0.019(3) 0.022(3) 0.002(2) 0.018(2) 0.000(2) C23 0.0339(16) 0.0336(16) 0.0317(16) -0.0017(10) 0.0087(10) -0.0021(10) C24 0.0336(16) 0.0328(16) 0.0321(15) -0.0010(10) 0.0090(10) -0.0032(10) C25 0.025(3) 0.026(3) 0.023(3) 0.001(2) 0.014(2) -0.001(2) C26 0.036(3) 0.024(3) 0.019(3) -0.008(2) 0.014(2) -0.003(2) C27 0.030(3) 0.018(3) 0.023(3) -0.003(2) 0.014(2) -0.005(2) N1 0.021(2) 0.018(2) 0.027(2) 0.0004(18) 0.0073(18) 0.0042(18) N2 0.024(3) 0.024(2) 0.029(2) 0.0005(19) 0.005(2) 0.0084(19) N3 0.027(3) 0.021(2) 0.021(2) 0.0004(18) 0.0135(19) 0.0050(19) N4 0.026(2) 0.022(2) 0.021(2) -0.0011(18) 0.0139(19) -0.0006(18) Ni1 0.0171(5) 0.0177(5) 0.0134(4) 0.0018(3) 0.0085(4) 0.0015(4) Ni2 0.0204(4) 0.0201(4) 0.0180(3) 0.0004(3) 0.0097(3) 0.0006(3) O1 0.026(2) 0.027(2) 0.0207(18) 0.0116(15) 0.0087(15) 0.0038(15) O2 0.0166(19) 0.0147(17) 0.0274(19) -0.0014(14) 0.0057(15) 0.0008(14) O3 0.026(2) 0.032(2) 0.0247(19) 0.0104(16) 0.0139(16) 0.0057(16) O4 0.021(2) 0.030(2) 0.0268(19) 0.0101(16) 0.0135(16) 0.0058(16) O5 0.029(2) 0.0231(19) 0.0166(17) 0.0037(15) 0.0093(15) 0.0059(16) O6 0.031(2) 0.028(2) 0.0251(19) 0.0067(15) 0.0180(16) 0.0069(16) O7 0.023(2) 0.022(2) 0.034(2) 0.0025(16) 0.0063(17) -0.0007(15) O8 0.049(3) 0.077(4) 0.073(3) 0.017(3) 0.016(3) 0.022(3) O9 0.30(3) 0.22(2) 0.24(2) -0.017(18) 0.09(2) -0.06(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 C1 O1 1.251(5) . ? C1 O2 1.263(5) . ? C1 C2 1.497(6) . ? C2 C9 1.384(6) . ? C2 C3 1.389(6) . ? C3 C4 1.388(6) . ? C3 H3 0.9300 . ? C4 C6 1.399(6) . ? C4 C5 1.501(6) . ? C5 O4 1.253(6) . ? C5 O3 1.257(5) . ? C5 Ni2 2.448(5) 1_655 ? C6 C7 1.384(6) . ? C6 H6 0.9300 . ? C7 C9 1.393(6) . ? C7 C8 1.502(6) . ? C8 O6 1.249(5) . ? C8 O5 1.264(5) . ? C8 Ni2 2.459(5) 4_666 ? C9 H9 0.9300 . ? C10 N1 1.324(6) . ? C10 N2 1.336(6) . ? C10 H10 0.9300 . ? C11 C12 1.325(7) . ? C11 N1 1.369(6) . ? C11 H11 0.9300 . ? C12 N2 1.361(6) . ? C12 H12 0.9300 . ? C13 C14 1.366(7) . ? C13 C18 1.370(7) . ? C13 N2 1.437(6) . ? C14 C15 1.377(7) . ? C14 H14 0.9300 . ? C15 C16 1.375(8) . ? C15 H15 0.9300 . ? C16 C17 1.384(8) . ? C16 C16 1.475(11) 3_655 ? C17 C18 1.382(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.341(6) . ? C19 N3 1.364(6) . ? C19 H19 0.9300 . ? C20 N4 1.381(6) . ? C20 H20 0.9300 . ? C21 N3 1.315(6) . ? C21 N4 1.347(6) . ? C21 H21 0.9300 . ? C22 C23 1.359(7) . ? C22 C27 1.377(6) . ? C22 N4 1.425(5) . ? C23 C24 1.370(7) . ? C23 H23 0.9300 . ? C24 C25 1.406(7) . ? C24 H24 0.9300 . ? C25 C26 1.386(7) . ? C25 C25 1.485(9) 3_664 ? C26 C27 1.386(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? N1 Ni2 2.016(4) . ? N3 Ni1 2.052(4) . ? Ni1 N3 2.052(4) 3_565 ? Ni1 O7 2.075(3) 3_565 ? Ni1 O7 2.075(3) . ? Ni1 O1 2.088(3) . ? Ni1 O1 2.088(3) 3_565 ? Ni2 O2 2.037(3) . ? Ni2 O4 2.054(3) 1_455 ? Ni2 O5 2.082(3) 4_565 ? Ni2 O3 2.193(3) 1_455 ? Ni2 O6 2.208(3) 4_565 ? Ni2 C5 2.448(5) 1_455 ? Ni2 C8 2.459(5) 4_565 ? O3 Ni2 2.193(3) 1_655 ? O4 Ni2 2.054(3) 1_655 ? O5 Ni2 2.082(3) 4_666 ? O6 Ni2 2.208(3) 4_666 ? O7 H7 0.8200 . ? O7 H7A 0.8169 . ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? O9 H9A 0.8500 . ? O9 H9B 0.8499 . ? 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 C1 O2 125.5(4) . . ? O1 C1 C2 116.3(4) . . ? O2 C1 C2 118.2(4) . . ? C9 C2 C3 119.3(4) . . ? C9 C2 C1 120.1(4) . . ? C3 C2 C1 120.6(4) . . ? C4 C3 C2 121.2(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C6 118.8(4) . . ? C3 C4 C5 120.9(4) . . ? C6 C4 C5 120.3(4) . . ? O4 C5 O3 120.0(4) . . ? O4 C5 C4 119.8(4) . . ? O3 C5 C4 120.2(4) . . ? O4 C5 Ni2 57.0(2) . 1_655 ? O3 C5 Ni2 63.3(3) . 1_655 ? C4 C5 Ni2 173.5(3) . 1_655 ? C7 C6 C4 120.4(4) . . ? C7 C6 H6 119.8 . . ? C4 C6 H6 119.8 . . ? C6 C7 C9 119.9(4) . . ? C6 C7 C8 120.1(4) . . ? C9 C7 C8 120.0(4) . . ? O6 C8 O5 120.7(4) . . ? O6 C8 C7 119.9(4) . . ? O5 C8 C7 119.4(4) . . ? O6 C8 Ni2 63.6(2) . 4_666 ? O5 C8 Ni2 57.8(2) . 4_666 ? C7 C8 Ni2 169.0(3) . 4_666 ? C2 C9 C7 120.3(4) . . ? C2 C9 H9 119.8 . . ? C7 C9 H9 119.8 . . ? N1 C10 N2 111.7(5) . . ? N1 C10 H10 124.2 . . ? N2 C10 H10 124.2 . . ? C12 C11 N1 110.2(5) . . ? C12 C11 H11 124.9 . . ? N1 C11 H11 124.9 . . ? C11 C12 N2 107.3(5) . . ? C11 C12 H12 126.4 . . ? N2 C12 H12 126.4 . . ? C14 C13 C18 118.9(5) . . ? C14 C13 N2 120.6(5) . . ? C18 C13 N2 120.4(5) . . ? C13 C14 C15 119.5(6) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 123.3(5) . . ? C16 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C15 C16 C17 116.1(5) . . ? C15 C16 C16 122.8(7) . 3_655 ? C17 C16 C16 121.1(7) . 3_655 ? C18 C17 C16 121.3(6) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C13 C18 C17 120.9(6) . . ? C13 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C20 C19 N3 110.4(5) . . ? C20 C19 H19 124.8 . . ? N3 C19 H19 124.8 . . ? C19 C20 N4 105.9(4) . . ? C19 C20 H20 127.1 . . ? N4 C20 H20 127.1 . . ? N3 C21 N4 111.0(4) . . ? N3 C21 H21 124.5 . . ? N4 C21 H21 124.5 . . ? C23 C22 C27 120.2(4) . . ? C23 C22 N4 120.2(4) . . ? C27 C22 N4 119.6(4) . . ? C22 C23 C24 120.5(5) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C25 121.4(5) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C26 C25 C24 116.5(4) . . ? C26 C25 C25 122.1(5) . 3_664 ? C24 C25 C25 121.3(6) . 3_664 ? C25 C26 C27 121.9(4) . . ? C25 C26 H26 119.1 . . ? C27 C26 H26 119.1 . . ? C22 C27 C26 119.4(4) . . ? C22 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C10 N1 C11 104.5(4) . . ? C10 N1 Ni2 125.8(3) . . ? C11 N1 Ni2 129.2(3) . . ? C10 N2 C12 106.3(4) . . ? C10 N2 C13 125.2(4) . . ? C12 N2 C13 127.9(4) . . ? C21 N3 C19 105.9(4) . . ? C21 N3 Ni1 127.6(3) . . ? C19 N3 Ni1 126.4(3) . . ? C21 N4 C20 106.9(4) . . ? C21 N4 C22 125.9(4) . . ? C20 N4 C22 127.2(4) . . ? N3 Ni1 N3 180.0 3_565 . ? N3 Ni1 O7 92.12(15) 3_565 3_565 ? N3 Ni1 O7 87.88(15) . 3_565 ? N3 Ni1 O7 87.88(15) 3_565 . ? N3 Ni1 O7 92.12(15) . . ? O7 Ni1 O7 180.00(13) 3_565 . ? N3 Ni1 O1 93.27(14) 3_565 . ? N3 Ni1 O1 86.73(14) . . ? O7 Ni1 O1 93.14(13) 3_565 . ? O7 Ni1 O1 86.86(13) . . ? N3 Ni1 O1 86.73(14) 3_565 3_565 ? N3 Ni1 O1 93.27(14) . 3_565 ? O7 Ni1 O1 86.86(13) 3_565 3_565 ? O7 Ni1 O1 93.14(13) . 3_565 ? O1 Ni1 O1 180.00(14) . 3_565 ? N1 Ni2 O2 101.41(15) . . ? N1 Ni2 O4 97.99(15) . 1_455 ? O2 Ni2 O4 102.57(13) . 1_455 ? N1 Ni2 O5 91.06(15) . 4_565 ? O2 Ni2 O5 92.74(12) . 4_565 ? O4 Ni2 O5 160.23(14) 1_455 4_565 ? N1 Ni2 O3 158.77(14) . 1_455 ? O2 Ni2 O3 89.17(13) . 1_455 ? O4 Ni2 O3 61.47(12) 1_455 1_455 ? O5 Ni2 O3 106.93(13) 4_565 1_455 ? N1 Ni2 O6 91.89(15) . 4_565 ? O2 Ni2 O6 151.04(13) . 4_565 ? O4 Ni2 O6 100.87(13) 1_455 4_565 ? O5 Ni2 O6 61.10(12) 4_565 4_565 ? O3 Ni2 O6 87.26(13) 1_455 4_565 ? N1 Ni2 C5 128.27(16) . 1_455 ? O2 Ni2 C5 98.54(14) . 1_455 ? O4 Ni2 C5 30.76(14) 1_455 1_455 ? O5 Ni2 C5 135.05(15) 4_565 1_455 ? O3 Ni2 C5 30.80(13) 1_455 1_455 ? O6 Ni2 C5 92.96(14) 4_565 1_455 ? N1 Ni2 C8 88.83(16) . 4_565 ? O2 Ni2 C8 123.35(14) . 4_565 ? O4 Ni2 C8 131.25(15) 1_455 4_565 ? O5 Ni2 C8 30.91(13) 4_565 4_565 ? O3 Ni2 C8 100.76(14) 1_455 4_565 ? O6 Ni2 C8 30.43(13) 4_565 4_565 ? C5 Ni2 C8 117.97(17) 1_455 4_565 ? C1 O1 Ni1 136.5(3) . . ? C1 O2 Ni2 128.3(3) . . ? C5 O3 Ni2 85.9(3) . 1_655 ? C5 O4 Ni2 92.3(3) . 1_655 ? C8 O5 Ni2 91.3(3) . 4_666 ? C8 O6 Ni2 86.0(3) . 4_666 ? Ni1 O7 H7 109.5 . . ? Ni1 O7 H7A 119.8 . . ? H7 O7 H7A 116.4 . . ? H8A O8 H8B 109.5 . . ? H9A O9 H9B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.980 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.104 # Attachment '5.cif' data_yy3 _database_code_depnum_ccdc_archive 'CCDC 742387' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H38 Cu3 N8 O15' _chemical_formula_weight 1229.57 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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9636(10) _cell_length_b 20.589(2) _cell_length_c 13.5194(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.469(2) _cell_angle_gamma 90.00 _cell_volume 2461.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1250 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6 _exptl_absorpt_correction_T_max 0.7 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13165 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.1526 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4826 _reflns_number_gt 2735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0000P)^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 4826 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 O9 O 0.0000 0.5000 0.0000 0.482(7) Uani 1 2 d S . . H9B H 0.0921 0.5108 0.0178 0.722 Uiso 0.50 1 d PR . . H9C H -0.0082 0.4762 -0.0519 0.722 Uiso 0.50 1 d PR . . O7 O 0.2538(7) 0.4312(2) -0.0322(4) 0.063(2) Uani 0.50 1 d P . . H7A H 0.1863 0.4509 -0.0728 0.094 Uiso 0.50 1 d PR . . H7C H 0.2221 0.4250 0.0229 0.094 Uiso 0.50 1 d PR . . C1 C 0.5882(4) 0.39066(17) -0.1264(3) 0.0360(13) Uani 1 1 d . . . H1 H 0.5437 0.3583 -0.0931 0.043 Uiso 1 1 calc R . . C2 C 0.6684(4) 0.38074(17) -0.2001(3) 0.0354(13) Uani 1 1 d . . . H2 H 0.6888 0.3409 -0.2273 0.043 Uiso 1 1 calc R . . C3 C 0.6573(4) 0.48363(17) -0.1687(3) 0.0264(11) Uani 1 1 d . . . H3 H 0.6707 0.5283 -0.1720 0.032 Uiso 1 1 calc R . . C4 C 0.8022(4) 0.45606(17) -0.3040(3) 0.0264(11) Uani 1 1 d . . . C5 C 0.8009(4) 0.41608(16) -0.3847(3) 0.0251(12) Uani 1 1 d . . . H5 H 0.7468 0.3774 -0.3889 0.030 Uiso 1 1 calc R . . C6 C 0.8804(4) 0.43340(17) -0.4600(3) 0.0288(12) Uani 1 1 d . . . H6 H 0.8805 0.4050 -0.5136 0.035 Uiso 1 1 calc R . . C7 C 0.9593(4) 0.49072(18) -0.4594(3) 0.0257(12) Uani 1 1 d . . . C8 C 0.9607(4) 0.52926(18) -0.3760(3) 0.0414(13) Uani 1 1 d . . . H8 H 1.0142 0.5681 -0.3719 0.050 Uiso 1 1 calc R . . C9 C 0.8859(5) 0.51239(18) -0.2984(3) 0.0447(14) Uani 1 1 d . . . H9 H 0.8920 0.5391 -0.2423 0.054 Uiso 1 1 calc R . . C10 C 0.5397(4) 0.19157(17) 0.2613(3) 0.0376(14) Uani 1 1 d . . . H10 H 0.4905 0.1996 0.3155 0.045 Uiso 1 1 calc R . . C11 C 0.6494(4) 0.14700(19) 0.2609(3) 0.0433(15) Uani 1 1 d . . . H11 H 0.6892 0.1193 0.3129 0.052 Uiso 1 1 calc R . . C12 C 0.6032(4) 0.19716(17) 0.1182(3) 0.0329(13) Uani 1 1 d . . . H12 H 0.6083 0.2094 0.0526 0.039 Uiso 1 1 calc R . . C13 C 0.7883(4) 0.10842(18) 0.1252(3) 0.0387(14) Uani 1 1 d . . . C14 C 0.8182(4) 0.04707(18) 0.1620(3) 0.0426(15) Uani 1 1 d . . . H14 H 0.7818 0.0330 0.2189 0.051 Uiso 1 1 calc R . . C15 C 0.9043(4) 0.00632(19) 0.1121(3) 0.0442(15) Uani 1 1 d . . . H15 H 0.9266 -0.0349 0.1386 0.053 Uiso 1 1 calc R . . C16 C 0.9584(4) 0.02265(18) 0.0267(4) 0.0404(15) Uani 1 1 d . . . C17 C 0.9304(5) 0.08616(19) -0.0048(4) 0.057 Uani 1 1 d . . . H17 H 0.9690 0.1010 -0.0605 0.069 Uiso 1 1 calc R . . C18 C 0.8465(5) 0.1282(2) 0.0440(4) 0.0681(18) Uani 1 1 d . . . H18 H 0.8300 0.1706 0.0208 0.082 Uiso 1 1 calc R . . C19 C 0.7965(4) 0.26624(16) 0.4446(3) 0.0250(11) Uani 1 1 d . . . C20 C 0.8249(4) 0.29541(16) 0.3469(3) 0.0212(11) Uani 1 1 d . . . C21 C 0.7075(4) 0.33205(16) 0.2927(3) 0.0210(11) Uani 1 1 d . . . C22 C 0.7343(4) 0.36196(16) 0.2044(3) 0.0213(11) Uani 1 1 d . . . C23 C 0.8716(4) 0.35678(16) 0.1716(3) 0.0242(11) Uani 1 1 d . . . H23 H 0.8871 0.3781 0.1135 0.029 Uiso 1 1 calc R . . C24 C 0.9876(4) 0.31943(16) 0.2257(3) 0.0236(11) Uani 1 1 d . . . C25 C 0.9619(4) 0.28873(17) 0.3122(3) 0.0240(11) Uani 1 1 d . . . H25 H 1.0376 0.2631 0.3479 0.029 Uiso 1 1 calc R . . C26 C 1.1349(4) 0.31264(17) 0.1893(3) 0.0265(12) Uani 1 1 d . . . C27 C 0.6062(4) 0.40028(17) 0.1424(3) 0.0271(12) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.0000 0.0325(2) Uani 1 2 d S . . Cu2 Cu 0.35548(5) 0.28735(2) 0.12343(4) 0.02746(14) Uani 1 1 d . . . N1 N 0.5817(3) 0.45607(14) -0.1074(2) 0.0252(9) Uani 1 1 d . . . N2 N 0.7150(3) 0.44082(14) -0.2279(2) 0.0279(10) Uani 1 1 d . . . N3 N 0.5106(3) 0.22322(14) 0.1720(2) 0.0302(10) Uani 1 1 d . . . N4 N 0.6902(3) 0.15088(15) 0.1679(3) 0.0358(11) Uani 1 1 d . . . O1 O 0.6905(3) 0.28672(12) 0.4826(2) 0.0380(8) Uani 1 1 d . . . O2 O 0.8895(3) 0.22281(11) 0.48450(19) 0.0288(8) Uani 1 1 d . . . O3 O 1.2378(3) 0.27778(12) 0.23812(19) 0.0319(8) Uani 1 1 d . . . O4 O 1.1554(3) 0.33869(12) 0.1094(2) 0.0318(8) Uani 1 1 d . . . O5 O 0.6431(3) 0.44800(12) 0.0946(2) 0.0352(9) Uani 1 1 d . . . O6 O 0.4730(3) 0.38180(11) 0.1445(2) 0.0359(9) Uani 1 1 d . . . O8 O 0.8717(13) 0.2655(5) 0.9540(11) 0.285(8) Uani 0.50 1 d P . . H8B H 0.9650 0.2631 0.9789 0.428 Uiso 0.50 1 d PR . . H8C H 0.8346 0.3002 0.9738 0.428 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 O9 0.349(10) 0.757(17) 0.248(9) 0.318(10) -0.221(8) -0.310(11) O7 0.123(5) 0.040(4) 0.023(4) -0.004(3) 0.004(4) -0.054(3) C1 0.051(3) 0.024(2) 0.039(3) 0.005(2) 0.024(2) 0.003(2) C2 0.052(3) 0.014(2) 0.046(3) -0.001(2) 0.025(2) -0.001(2) C3 0.037(2) 0.022(2) 0.021(2) 0.0035(18) 0.008(2) 0.0072(19) C4 0.029(2) 0.025(2) 0.028(2) -0.0006(19) 0.013(2) 0.0065(19) C5 0.025(2) 0.018(2) 0.032(3) -0.0008(19) 0.005(2) -0.0013(18) C6 0.032(2) 0.030(2) 0.027(2) -0.007(2) 0.013(2) 0.0008(19) C7 0.020(2) 0.029(2) 0.029(3) -0.009(2) 0.0074(19) -0.0008(18) C8 0.058(3) 0.034(2) 0.042(3) -0.018(2) 0.034(2) -0.029(2) C9 0.064(3) 0.034(3) 0.043(3) -0.018(2) 0.030(3) -0.017(2) C10 0.032(2) 0.044(3) 0.037(3) 0.002(2) 0.006(2) 0.005(2) C11 0.027(3) 0.048(3) 0.053(3) 0.004(3) 0.002(3) 0.004(2) C12 0.031(2) 0.028(2) 0.039(3) 0.002(2) 0.000(2) 0.001(2) C13 0.024(2) 0.036(3) 0.058(3) 0.001(2) 0.012(2) 0.002(2) C14 0.036(3) 0.037(3) 0.054(3) -0.001(2) 0.002(3) 0.008(2) C15 0.040(3) 0.024(2) 0.063(4) -0.003(2) -0.008(3) 0.015(2) C16 0.019(2) 0.025(3) 0.079(4) -0.003(2) 0.014(2) 0.0031(18) C17 0.046 0.033 0.099 0.003 0.029 0.016 C18 0.068(3) 0.035(3) 0.115(5) 0.017(3) 0.056(3) 0.024(2) C19 0.026(2) 0.024(2) 0.026(2) -0.0085(19) 0.007(2) -0.0040(18) C20 0.027(2) 0.017(2) 0.020(2) -0.0016(18) 0.0057(19) -0.0029(18) C21 0.036(2) 0.0115(19) 0.014(2) -0.0038(17) 0.000(2) -0.0037(18) C22 0.015(2) 0.022(2) 0.027(3) -0.0022(18) 0.0024(19) 0.0039(17) C23 0.026(2) 0.023(2) 0.024(2) 0.0004(18) 0.004(2) -0.0018(18) C24 0.023(2) 0.026(2) 0.025(2) -0.0007(19) 0.0114(19) 0.0033(18) C25 0.024(2) 0.023(2) 0.026(2) -0.003(2) 0.0050(19) 0.0024(19) C26 0.030(2) 0.023(2) 0.026(3) -0.0077(19) 0.003(2) -0.0002(18) C27 0.030(2) 0.027(2) 0.024(3) -0.0075(19) 0.004(2) 0.0097(19) Cu1 0.0432(4) 0.0339(4) 0.0245(4) 0.0104(4) 0.0178(4) 0.0168(4) Cu2 0.0222(3) 0.0333(3) 0.0283(3) -0.0019(3) 0.0086(2) 0.0044(2) N1 0.037(2) 0.0268(19) 0.0157(18) 0.0033(15) 0.0170(16) 0.0073(16) N2 0.032(2) 0.0259(19) 0.028(2) -0.0037(16) 0.0118(17) 0.0012(16) N3 0.0224(18) 0.029(2) 0.038(2) -0.0038(17) 0.0030(17) 0.0041(16) N4 0.0251(19) 0.031(2) 0.053(3) 0.0004(19) 0.010(2) 0.0034(16) O1 0.0388(16) 0.0422(17) 0.0392(18) 0.0089(15) 0.0248(14) 0.0094(15) O2 0.0305(15) 0.0317(16) 0.0246(16) 0.0064(13) 0.0061(14) 0.0049(13) O3 0.0281(15) 0.0451(17) 0.0255(17) 0.0099(14) 0.0136(13) 0.0182(14) O4 0.0247(15) 0.0470(18) 0.0264(17) 0.0102(14) 0.0122(14) 0.0099(13) O5 0.0355(17) 0.0383(17) 0.0335(18) 0.0175(14) 0.0107(15) 0.0137(14) O6 0.0248(16) 0.0249(16) 0.055(2) -0.0053(14) -0.0038(16) 0.0063(13) O8 0.271(13) 0.208(13) 0.42(2) 0.043(12) 0.187(13) -0.004(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O9 H9B 0.8500 . ? O9 H9C 0.8499 . ? O7 Cu1 2.598(5) . ? O7 H7A 0.8500 . ? O7 H7C 0.8501 . ? C1 C2 1.336(6) . ? C1 N1 1.374(4) . ? C1 H1 0.9300 . ? C2 N2 1.378(4) . ? C2 H2 0.9300 . ? C3 N1 1.285(5) . ? C3 N2 1.349(5) . ? C3 H3 0.9300 . ? C4 C5 1.365(5) . ? C4 C9 1.376(5) . ? C4 N2 1.426(5) . ? C5 C6 1.382(5) . ? C5 H5 0.9300 . ? C6 C7 1.375(5) . ? C6 H6 0.9300 . ? C7 C8 1.377(5) . ? C7 C7 1.466(7) 3_764 ? C8 C9 1.379(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.346(5) . ? C10 N3 1.359(5) . ? C10 H10 0.9300 . ? C11 N4 1.368(6) . ? C11 H11 0.9300 . ? C12 N3 1.306(5) . ? C12 N4 1.339(4) . ? C12 H12 0.9300 . ? C13 C18 1.354(7) . ? C13 C14 1.368(5) . ? C13 N4 1.427(5) . ? C14 C15 1.388(5) . ? C14 H14 0.9300 . ? C15 C16 1.366(6) . ? C15 H15 0.9300 . ? C16 C17 1.385(5) . ? C16 C16 1.457(8) 3_755 ? C17 C18 1.383(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 O1 1.227(4) . ? C19 O2 1.280(4) . ? C19 C20 1.510(5) . ? C20 C25 1.391(5) . ? C20 C21 1.400(4) . ? C21 C22 1.399(5) . ? C22 C23 1.379(5) . ? C22 C27 1.526(5) . ? C23 C24 1.399(4) . ? C23 H23 0.9300 . ? C24 C25 1.382(5) . ? C24 C26 1.488(5) . ? C25 H25 0.9300 . ? C26 O4 1.247(4) . ? C26 O3 1.265(4) . ? C26 Cu2 2.357(4) 1_655 ? C27 O5 1.250(4) . ? C27 O6 1.258(4) . ? Cu1 N1 1.953(3) . ? Cu1 N1 1.953(3) 3_665 ? Cu1 O5 1.972(2) . ? Cu1 O5 1.972(2) 3_665 ? Cu2 N3 1.951(3) . ? Cu2 O2 1.963(3) 4_565 ? Cu2 O3 2.024(3) 1_455 ? Cu2 O4 2.063(2) 1_455 ? Cu2 O6 2.208(2) . ? Cu2 C26 2.357(4) 1_455 ? O2 Cu2 1.963(3) 4_666 ? O3 Cu2 2.024(3) 1_655 ? O4 Cu2 2.063(2) 1_655 ? O8 H8B 0.8501 . ? O8 H8C 0.8502 . ? 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 H9B O9 H9C 109.5 . . ? Cu1 O7 H7A 110.1 . . ? Cu1 O7 H7C 109.4 . . ? H7A O7 H7C 109.4 . . ? C2 C1 N1 109.5(3) . . ? C2 C1 H1 125.3 . . ? N1 C1 H1 125.3 . . ? C1 C2 N2 106.9(3) . . ? C1 C2 H2 126.5 . . ? N2 C2 H2 126.5 . . ? N1 C3 N2 112.8(3) . . ? N1 C3 H3 123.6 . . ? N2 C3 H3 123.6 . . ? C5 C4 C9 119.0(4) . . ? C5 C4 N2 120.7(3) . . ? C9 C4 N2 120.3(4) . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 122.9(4) . . ? C7 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C6 C7 C8 115.8(4) . . ? C6 C7 C7 122.5(4) . 3_764 ? C8 C7 C7 121.6(4) . 3_764 ? C7 C8 C9 122.5(4) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C4 C9 C8 119.9(4) . . ? C4 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 N3 110.9(4) . . ? C11 C10 H10 124.5 . . ? N3 C10 H10 124.5 . . ? C10 C11 N4 105.7(4) . . ? C10 C11 H11 127.2 . . ? N4 C11 H11 127.2 . . ? N3 C12 N4 112.6(4) . . ? N3 C12 H12 123.7 . . ? N4 C12 H12 123.7 . . ? C18 C13 C14 119.6(4) . . ? C18 C13 N4 119.2(4) . . ? C14 C13 N4 121.0(4) . . ? C13 C14 C15 118.2(4) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C16 C15 C14 124.4(4) . . ? C16 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? C15 C16 C17 114.9(4) . . ? C15 C16 C16 122.9(5) . 3_755 ? C17 C16 C16 122.3(6) . 3_755 ? C18 C17 C16 122.0(5) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C13 C18 C17 120.7(4) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? O1 C19 O2 124.0(4) . . ? O1 C19 C20 118.9(3) . . ? O2 C19 C20 117.0(3) . . ? C25 C20 C21 120.4(3) . . ? C25 C20 C19 122.8(3) . . ? C21 C20 C19 116.8(3) . . ? C22 C21 C20 117.6(3) . . ? C23 C22 C21 121.9(3) . . ? C23 C22 C27 119.6(3) . . ? C21 C22 C27 118.5(3) . . ? C22 C23 C24 120.0(4) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 118.7(4) . . ? C25 C24 C26 121.1(3) . . ? C23 C24 C26 120.2(3) . . ? C24 C25 C20 121.3(3) . . ? C24 C25 H25 119.3 . . ? C20 C25 H25 119.3 . . ? O4 C26 O3 119.8(4) . . ? O4 C26 C24 120.7(3) . . ? O3 C26 C24 119.4(3) . . ? O4 C26 Cu2 61.0(2) . 1_655 ? O3 C26 Cu2 59.1(2) . 1_655 ? C24 C26 Cu2 171.9(3) . 1_655 ? O5 C27 O6 125.6(3) . . ? O5 C27 C22 116.8(3) . . ? O6 C27 C22 117.5(3) . . ? N1 Cu1 N1 180.000(1) . 3_665 ? N1 Cu1 O5 86.97(11) . . ? N1 Cu1 O5 93.03(11) 3_665 . ? N1 Cu1 O5 93.03(11) . 3_665 ? N1 Cu1 O5 86.97(11) 3_665 3_665 ? O5 Cu1 O5 180.0 . 3_665 ? N1 Cu1 O7 92.02(15) . . ? N1 Cu1 O7 87.98(15) 3_665 . ? O5 Cu1 O7 104.89(13) . . ? O5 Cu1 O7 75.11(14) 3_665 . ? N3 Cu2 O2 92.04(12) . 4_565 ? N3 Cu2 O3 96.25(12) . 1_455 ? O2 Cu2 O3 154.90(10) 4_565 1_455 ? N3 Cu2 O4 159.72(13) . 1_455 ? O2 Cu2 O4 103.67(10) 4_565 1_455 ? O3 Cu2 O4 64.24(10) 1_455 1_455 ? N3 Cu2 O6 104.72(11) . . ? O2 Cu2 O6 94.08(10) 4_565 . ? O3 Cu2 O6 106.55(10) 1_455 . ? O4 Cu2 O6 87.12(10) 1_455 . ? N3 Cu2 C26 128.17(14) . 1_455 ? O2 Cu2 C26 131.11(11) 4_565 1_455 ? O3 Cu2 C26 32.45(10) 1_455 1_455 ? O4 Cu2 C26 31.89(11) 1_455 1_455 ? O6 Cu2 C26 99.73(11) . 1_455 ? C3 N1 C1 105.6(3) . . ? C3 N1 Cu1 125.2(3) . . ? C1 N1 Cu1 128.7(3) . . ? C3 N2 C2 105.2(3) . . ? C3 N2 C4 126.4(3) . . ? C2 N2 C4 128.4(3) . . ? C12 N3 C10 104.5(3) . . ? C12 N3 Cu2 125.0(3) . . ? C10 N3 Cu2 130.2(3) . . ? C12 N4 C11 106.3(3) . . ? C12 N4 C13 125.4(4) . . ? C11 N4 C13 127.7(3) . . ? C19 O2 Cu2 106.5(2) . 4_666 ? C26 O3 Cu2 88.4(2) . 1_655 ? C26 O4 Cu2 87.1(2) . 1_655 ? C27 O5 Cu1 124.2(2) . . ? C27 O6 Cu2 134.3(2) . . ? H8B O8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.533 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.088