# Electronic 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 'Jian-Zhong Cui' _publ_contact_author_email CUIJIANZHONG@TJU.EDU.CN _publ_section_title ; ds-block metal ions catalyzed decarboxylation of pyrazine-2,3,5,6-tetracarboxylic acid and the complexes obtained from hydrothermal reactions and novel water clusters ; loop_ _publ_author_name 'Jian-Zhong Cui' 'Peng Cheng' 'Su-Rong Fang' 'Hong-Ling Gao' ; Ying-Ping Quan ; 'Wei Shi' 'Jian-Hui Wang' 'Ai-Hong Yang' 'Yan-Ping Zhang' ; Li-Hua Zhao ; # Attachment 'complex 3.cif' data_70203a _database_code_depnum_ccdc_archive 'CCDC 648150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N6 O12 Zn2' _chemical_formula_weight 767.27 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 9.2844(11) _cell_length_b 20.105(2) _cell_length_c 7.6606(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.057(2) _cell_angle_gamma 90.00 _cell_volume 1408.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4564 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.30 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.785 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.601895 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 7998 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2861 _reflns_number_gt 2490 _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^)+(0.0376P)^2^+0.6635P] 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 2861 _refine_ls_number_parameters 217 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0714 _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 Zn1 Zn 0.22150(3) 0.576109(11) 0.20898(3) 0.02035(10) Uani 1 1 d . . . O1 O 0.12497(17) 0.55151(7) -0.04690(18) 0.0221(3) Uani 1 1 d . . . O2 O 0.17816(19) 0.44293(8) -0.0721(2) 0.0288(4) Uani 1 1 d . . . O3 O 0.36557(18) 0.53330(10) -0.2685(2) 0.0383(4) Uani 1 1 d . . . O4 O 0.33513(18) 0.58650(8) -0.5274(2) 0.0268(4) Uani 1 1 d . . . O5 O 0.33902(18) 0.48252(8) 0.2263(2) 0.0309(4) Uani 1 1 d D . . H5A H 0.4321 0.4766 0.2428 0.037 Uiso 1 1 d RD . . H5B H 0.2945 0.4679 0.1252 0.037 Uiso 1 1 d RD . . N1 N 0.07329(18) 0.52590(8) -0.6277(2) 0.0173(4) Uani 1 1 d . . . N2 N 0.1141(2) 0.67180(9) 0.2207(2) 0.0236(4) Uani 1 1 d . . . N3 N 0.3733(2) 0.64380(9) 0.1312(2) 0.0238(4) Uani 1 1 d . . . C1 C 0.1298(2) 0.49748(10) -0.1297(3) 0.0180(4) Uani 1 1 d . . . C2 C 0.0621(2) 0.49962(10) -0.3262(2) 0.0164(4) Uani 1 1 d . . . C3 C 0.1361(2) 0.52476(10) -0.4558(3) 0.0169(4) Uani 1 1 d . . . C4 C 0.2934(2) 0.55054(11) -0.4121(3) 0.0197(4) Uani 1 1 d . . . C5 C -0.0163(3) 0.68335(12) 0.2684(3) 0.0299(5) Uani 1 1 d . . . H5 H -0.0752 0.6472 0.2842 0.036 Uiso 1 1 calc R . . C6 C -0.0667(3) 0.74656(13) 0.2951(3) 0.0340(6) Uani 1 1 d . . . H6 H -0.1580 0.7527 0.3269 0.041 Uiso 1 1 calc R . . C7 C 0.0204(3) 0.80051(12) 0.2739(3) 0.0359(6) Uani 1 1 d . . . H7 H -0.0104 0.8435 0.2927 0.043 Uiso 1 1 calc R . . C8 C 0.1543(3) 0.78929(12) 0.2242(3) 0.0325(5) Uani 1 1 d . . . H8 H 0.2149 0.8249 0.2092 0.039 Uiso 1 1 calc R . . C9 C 0.1983(2) 0.72458(11) 0.1966(3) 0.0234(5) Uani 1 1 d . . . C10 C 0.3399(2) 0.70905(11) 0.1394(3) 0.0237(5) Uani 1 1 d . . . C11 C 0.4330(3) 0.75802(12) 0.0949(3) 0.0311(5) Uani 1 1 d . . . H11 H 0.4086 0.8027 0.1009 0.037 Uiso 1 1 calc R . . C12 C 0.5615(3) 0.73970(12) 0.0421(3) 0.0361(6) Uani 1 1 d . . . H12 H 0.6247 0.7720 0.0121 0.043 Uiso 1 1 calc R . . C13 C 0.5962(3) 0.67291(13) 0.0340(4) 0.0380(6) Uani 1 1 d . . . H13 H 0.6826 0.6595 -0.0013 0.046 Uiso 1 1 calc R . . C14 C 0.4987(3) 0.62662(12) 0.0796(3) 0.0316(5) Uani 1 1 d . . . H14 H 0.5213 0.5817 0.0743 0.038 Uiso 1 1 calc R . . O6 O 0.2924(4) 0.38667(13) 0.5054(4) 0.0972(10) Uani 1 1 d D . . H6A H 0.3147 0.4000 0.4066 0.117 Uiso 1 1 d RD . . H6B H 0.3496 0.3995 0.5991 0.117 Uiso 1 1 d RD . . 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 Zn1 0.02437(16) 0.01888(15) 0.01709(14) -0.00063(9) 0.00168(10) -0.00304(10) O1 0.0270(8) 0.0213(8) 0.0164(7) -0.0019(6) -0.0005(6) 0.0009(6) O2 0.0374(10) 0.0204(8) 0.0239(8) -0.0001(6) -0.0079(7) 0.0042(7) O3 0.0193(9) 0.0683(13) 0.0245(8) 0.0115(8) -0.0043(7) -0.0087(8) O4 0.0265(9) 0.0306(9) 0.0217(8) 0.0005(6) -0.0004(6) -0.0108(7) O5 0.0222(9) 0.0364(9) 0.0300(9) -0.0071(7) -0.0069(7) 0.0050(7) N1 0.0183(9) 0.0175(9) 0.0151(8) -0.0017(6) 0.0004(7) 0.0015(7) N2 0.0274(10) 0.0194(9) 0.0227(9) -0.0017(7) 0.0011(7) -0.0020(7) N3 0.0266(10) 0.0223(9) 0.0222(9) 0.0014(7) 0.0030(7) -0.0019(8) C1 0.0147(10) 0.0222(11) 0.0166(9) 0.0000(8) 0.0017(8) -0.0023(8) C2 0.0167(10) 0.0160(10) 0.0157(9) -0.0014(7) 0.0006(7) 0.0012(8) C3 0.0168(10) 0.0165(10) 0.0163(9) -0.0025(7) -0.0001(8) 0.0011(8) C4 0.0178(11) 0.0234(11) 0.0177(10) -0.0057(8) 0.0022(8) -0.0024(8) C5 0.0296(13) 0.0271(12) 0.0327(12) -0.0041(10) 0.0050(10) -0.0047(10) C6 0.0300(13) 0.0348(13) 0.0365(13) -0.0054(11) 0.0038(10) 0.0045(10) C7 0.0433(16) 0.0239(12) 0.0383(13) -0.0040(10) 0.0015(11) 0.0067(11) C8 0.0372(15) 0.0217(12) 0.0368(13) 0.0022(10) 0.0016(10) -0.0017(10) C9 0.0275(12) 0.0215(11) 0.0189(10) 0.0001(8) -0.0021(8) -0.0012(9) C10 0.0271(12) 0.0228(11) 0.0191(10) 0.0020(8) -0.0016(9) -0.0007(9) C11 0.0341(14) 0.0216(12) 0.0359(13) 0.0061(9) 0.0015(10) -0.0025(10) C12 0.0327(14) 0.0319(14) 0.0437(14) 0.0092(11) 0.0066(11) -0.0082(11) C13 0.0317(14) 0.0359(14) 0.0491(15) 0.0073(12) 0.0150(12) 0.0006(11) C14 0.0350(14) 0.0256(12) 0.0355(13) 0.0033(10) 0.0092(10) 0.0012(10) O6 0.156(3) 0.0535(16) 0.0786(19) 0.0026(14) 0.0113(19) 0.0115(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 Zn1 O1 2.0680(14) . ? Zn1 N3 2.1184(18) . ? Zn1 O4 2.1188(15) 1_556 ? Zn1 O5 2.1675(16) . ? Zn1 N2 2.1761(18) . ? Zn1 N1 2.2538(17) 1_556 ? O1 C1 1.263(2) . ? O2 C1 1.237(3) . ? O3 C4 1.234(3) . ? O4 C4 1.255(3) . ? O4 Zn1 2.1189(15) 1_554 ? O5 H5A 0.8590 . ? O5 H5B 0.8632 . ? N1 C3 1.344(3) . ? N1 C2 1.346(3) 3_564 ? N1 Zn1 2.2539(17) 1_554 ? N2 C5 1.345(3) . ? N2 C9 1.349(3) . ? N3 C14 1.338(3) . ? N3 C10 1.352(3) . ? C1 C2 1.528(3) . ? C2 N1 1.346(3) 3_564 ? C2 C3 1.397(3) . ? C3 C4 1.530(3) . ? C5 C6 1.382(3) . ? C5 H5 0.9300 . ? C6 C7 1.380(4) . ? C6 H6 0.9300 . ? C7 C8 1.381(4) . ? C7 H7 0.9300 . ? C8 C9 1.391(3) . ? C8 H8 0.9300 . ? C9 C10 1.490(3) . ? C10 C11 1.392(3) . ? C11 C12 1.374(4) . ? C11 H11 0.9300 . ? C12 C13 1.385(4) . ? C12 H12 0.9300 . ? C13 C14 1.385(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? O6 H6A 0.8615 . ? O6 H6B 0.8549 . ? 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 Zn1 N3 94.96(6) . . ? O1 Zn1 O4 171.15(6) . 1_556 ? N3 Zn1 O4 87.69(6) . 1_556 ? O1 Zn1 O5 88.89(6) . . ? N3 Zn1 O5 102.84(7) . . ? O4 Zn1 O5 82.29(6) 1_556 . ? O1 Zn1 N2 97.16(6) . . ? N3 Zn1 N2 77.04(7) . . ? O4 Zn1 N2 91.66(6) 1_556 . ? O5 Zn1 N2 173.94(6) . . ? O1 Zn1 N1 102.34(6) . 1_556 ? N3 Zn1 N1 160.85(6) . 1_556 ? O4 Zn1 N1 76.46(6) 1_556 1_556 ? O5 Zn1 N1 85.81(6) . 1_556 ? N2 Zn1 N1 92.55(7) . 1_556 ? C1 O1 Zn1 129.37(13) . . ? C4 O4 Zn1 116.79(13) . 1_554 ? Zn1 O5 H5A 127.7 . . ? Zn1 O5 H5B 94.8 . . ? H5A O5 H5B 113.4 . . ? C3 N1 C2 118.44(17) . 3_564 ? C3 N1 Zn1 110.42(13) . 1_554 ? C2 N1 Zn1 131.11(13) 3_564 1_554 ? C5 N2 C9 118.15(19) . . ? C5 N2 Zn1 127.21(15) . . ? C9 N2 Zn1 114.16(15) . . ? C14 N3 C10 118.87(19) . . ? C14 N3 Zn1 124.96(15) . . ? C10 N3 Zn1 116.15(15) . . ? O2 C1 O1 128.80(19) . . ? O2 C1 C2 115.94(17) . . ? O1 C1 C2 115.23(17) . . ? N1 C2 C3 120.27(18) 3_564 . ? N1 C2 C1 116.91(17) 3_564 . ? C3 C2 C1 122.79(18) . . ? N1 C3 C2 121.27(19) . . ? N1 C3 C4 116.31(17) . . ? C2 C3 C4 122.41(17) . . ? O3 C4 O4 127.1(2) . . ? O3 C4 C3 116.70(18) . . ? O4 C4 C3 116.19(17) . . ? N2 C5 C6 122.9(2) . . ? N2 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? C7 C6 C5 119.0(2) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 118.6(2) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C7 C8 C9 119.8(2) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N2 C9 C8 121.5(2) . . ? N2 C9 C10 115.93(19) . . ? C8 C9 C10 122.6(2) . . ? N3 C10 C11 121.2(2) . . ? N3 C10 C9 116.02(19) . . ? C11 C10 C9 122.8(2) . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.6(2) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 118.2(2) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? N3 C14 C13 122.8(2) . . ? N3 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? H6A O6 H6B 115.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Zn1 O1 C1 110.76(18) . . . . ? O4 Zn1 O1 C1 3.7(5) 1_556 . . . ? O5 Zn1 O1 C1 7.97(17) . . . . ? N2 Zn1 O1 C1 -171.71(17) . . . . ? N1 Zn1 O1 C1 -77.50(18) 1_556 . . . ? O1 Zn1 N2 C5 87.24(18) . . . . ? N3 Zn1 N2 C5 -179.30(19) . . . . ? O4 Zn1 N2 C5 -92.05(18) 1_556 . . . ? O5 Zn1 N2 C5 -89.7(7) . . . . ? N1 Zn1 N2 C5 -15.54(19) 1_556 . . . ? O1 Zn1 N2 C9 -101.01(14) . . . . ? N3 Zn1 N2 C9 -7.54(14) . . . . ? O4 Zn1 N2 C9 79.70(14) 1_556 . . . ? O5 Zn1 N2 C9 82.1(7) . . . . ? N1 Zn1 N2 C9 156.21(14) 1_556 . . . ? O1 Zn1 N3 C14 -80.43(18) . . . . ? O4 Zn1 N3 C14 91.11(18) 1_556 . . . ? O5 Zn1 N3 C14 9.56(19) . . . . ? N2 Zn1 N3 C14 -176.66(19) . . . . ? N1 Zn1 N3 C14 124.9(2) 1_556 . . . ? O1 Zn1 N3 C10 101.17(15) . . . . ? O4 Zn1 N3 C10 -87.30(15) 1_556 . . . ? O5 Zn1 N3 C10 -168.85(14) . . . . ? N2 Zn1 N3 C10 4.94(14) . . . . ? N1 Zn1 N3 C10 -53.5(3) 1_556 . . . ? Zn1 O1 C1 O2 10.0(3) . . . . ? Zn1 O1 C1 C2 -172.18(13) . . . . ? O2 C1 C2 N1 77.2(2) . . . 3_564 ? O1 C1 C2 N1 -101.0(2) . . . 3_564 ? O2 C1 C2 C3 -101.0(2) . . . . ? O1 C1 C2 C3 80.9(2) . . . . ? C2 N1 C3 C2 -1.9(3) 3_564 . . . ? Zn1 N1 C3 C2 176.24(15) 1_554 . . . ? C2 N1 C3 C4 176.45(17) 3_564 . . . ? Zn1 N1 C3 C4 -5.4(2) 1_554 . . . ? N1 C2 C3 N1 1.9(3) 3_564 . . . ? C1 C2 C3 N1 180.00(18) . . . . ? N1 C2 C3 C4 -176.32(18) 3_564 . . . ? C1 C2 C3 C4 1.8(3) . . . . ? Zn1 O4 C4 O3 156.46(19) 1_554 . . . ? Zn1 O4 C4 C3 -22.8(2) 1_554 . . . ? N1 C3 C4 O3 -160.4(2) . . . . ? C2 C3 C4 O3 17.9(3) . . . . ? N1 C3 C4 O4 18.9(3) . . . . ? C2 C3 C4 O4 -162.74(19) . . . . ? C9 N2 C5 C6 -0.6(3) . . . . ? Zn1 N2 C5 C6 170.90(17) . . . . ? N2 C5 C6 C7 -0.7(4) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C5 N2 C9 C8 1.6(3) . . . . ? Zn1 N2 C9 C8 -171.00(17) . . . . ? C5 N2 C9 C10 -178.52(18) . . . . ? Zn1 N2 C9 C10 8.9(2) . . . . ? C7 C8 C9 N2 -1.3(3) . . . . ? C7 C8 C9 C10 178.8(2) . . . . ? C14 N3 C10 C11 0.2(3) . . . . ? Zn1 N3 C10 C11 178.70(16) . . . . ? C14 N3 C10 C9 179.59(19) . . . . ? Zn1 N3 C10 C9 -1.9(2) . . . . ? N2 C9 C10 N3 -4.9(3) . . . . ? C8 C9 C10 N3 175.0(2) . . . . ? N2 C9 C10 C11 174.5(2) . . . . ? C8 C9 C10 C11 -5.6(3) . . . . ? N3 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C12 -179.5(2) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 C14 0.1(4) . . . . ? C10 N3 C14 C13 -0.1(3) . . . . ? Zn1 N3 C14 C13 -178.43(19) . . . . ? C12 C13 C14 N3 -0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.325 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.082 # Attachment 'complex 5.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 664597' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Cu2 N6 O13' _chemical_formula_weight 781.63 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 11.182(2) _cell_length_b 12.088(2) _cell_length_c 13.495(3) _cell_angle_alpha 97.61(3) _cell_angle_beta 97.61(3) _cell_angle_gamma 116.83(3) _cell_volume 1574.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12260 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 27.42 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 1.427 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8832 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _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 'SCX min' _diffrn_measurement_method w\ _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13384 _diffrn_reflns_av_R_equivalents 0.1034 _diffrn_reflns_av_sigmaI/netI 0.1364 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5501 _reflns_number_gt 3368 _reflns_threshold_expression I>2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _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^)+(0.0418P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5501 _refine_ls_number_parameters 472 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1342 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.65408(8) 0.75065(7) 1.01642(6) 0.0257(2) Uani 1 1 d . . . Cu2 Cu 0.58515(8) 0.79228(7) 0.61141(6) 0.0239(2) Uani 1 1 d . . . C1 C 0.3740(6) 0.5220(5) 0.5347(4) 0.0187(14) Uani 1 1 d . . . C2 C 0.2932(5) 0.3937(5) 0.5369(4) 0.0178(14) Uani 1 1 d . . . C3 C 0.3549(6) 0.4438(5) 0.7143(4) 0.0171(13) Uani 1 1 d . . . C4 C 0.4416(6) 0.5716(5) 0.7124(4) 0.0195(14) Uani 1 1 d . . . C5 C 0.3815(7) 0.5744(6) 0.4367(5) 0.0256(15) Uani 1 1 d . . . C6 C 0.2067(7) 0.2902(6) 0.4396(5) 0.0271(16) Uani 1 1 d . . . C7 C 0.3256(7) 0.3933(5) 0.8117(4) 0.0229(15) Uani 1 1 d . . . C8 C 0.5290(6) 0.6739(6) 0.8082(4) 0.0214(14) Uani 1 1 d . . . C9 C 0.3182(7) 0.8013(7) 0.6026(5) 0.0399(18) Uani 1 1 d . . . H9A H 0.2767 0.7133 0.5929 0.048 Uiso 1 1 calc R . . C10 C 0.2355(8) 0.8590(9) 0.6029(5) 0.052(2) Uani 1 1 d . . . H10A H 0.1407 0.8111 0.5929 0.063 Uiso 1 1 calc R . . C11 C 0.2987(10) 0.9902(9) 0.6186(6) 0.059(2) Uani 1 1 d . . . H11A H 0.2462 1.0317 0.6206 0.071 Uiso 1 1 calc R . . C12 C 0.4373(9) 1.0583(8) 0.6313(5) 0.049(2) Uani 1 1 d . . . H12A H 0.4798 1.1463 0.6406 0.059 Uiso 1 1 calc R . . C13 C 0.7513(9) 1.1910(7) 0.6622(6) 0.054(2) Uani 1 1 d . . . H13A H 0.7143 1.2459 0.6711 0.064 Uiso 1 1 calc R . . C14 C 0.8898(10) 1.2398(8) 0.6694(6) 0.068(3) Uani 1 1 d . . . H14A H 0.9461 1.3272 0.6820 0.081 Uiso 1 1 calc R . . C15 C 0.9449(8) 1.1605(7) 0.6580(6) 0.059(2) Uani 1 1 d . . . H15A H 1.0388 1.1925 0.6626 0.070 Uiso 1 1 calc R . . C16 C 0.8573(7) 1.0293(6) 0.6393(5) 0.0396(18) Uani 1 1 d . . . H16A H 0.8950 0.9749 0.6314 0.048 Uiso 1 1 calc R . . C17 C 0.6639(7) 1.0585(6) 0.6415(5) 0.0322(17) Uani 1 1 d . . . C18 C 0.5147(7) 0.9950(6) 0.6301(5) 0.0304(16) Uani 1 1 d . . . C19 C 0.9419(7) 0.9645(6) 1.1096(5) 0.0384(18) Uani 1 1 d . . . H19A H 0.9717 0.9060 1.0904 0.046 Uiso 1 1 calc R . . C20 C 1.0399(8) 1.0898(7) 1.1548(5) 0.050(2) Uani 1 1 d . . . H20A H 1.1332 1.1144 1.1676 0.060 Uiso 1 1 calc R . . C21 C 0.9937(8) 1.1759(7) 1.1800(5) 0.053(2) Uani 1 1 d . . . H21A H 1.0567 1.2605 1.2085 0.064 Uiso 1 1 calc R . . C22 C 0.8533(8) 1.1371(6) 1.1630(5) 0.045(2) Uani 1 1 d . . . H22A H 0.8218 1.1950 1.1794 0.054 Uiso 1 1 calc R . . C23 C 0.5404(8) 1.0180(6) 1.1323(5) 0.0386(19) Uani 1 1 d . . . H23A H 0.5885 1.1031 1.1657 0.046 Uiso 1 1 calc R . . C24 C 0.3983(9) 0.9547(7) 1.1132(5) 0.045(2) Uani 1 1 d . . . H24A H 0.3516 0.9981 1.1327 0.054 Uiso 1 1 calc R . . C25 C 0.3246(8) 0.8261(7) 1.0647(5) 0.0408(19) Uani 1 1 d . . . H25A H 0.2293 0.7813 1.0534 0.049 Uiso 1 1 calc R . . C26 C 0.4019(7) 0.7684(7) 1.0340(5) 0.0404(19) Uani 1 1 d . . . H26A H 0.3560 0.6836 0.9998 0.048 Uiso 1 1 calc R . . C27 C 0.6112(7) 0.9551(6) 1.1018(4) 0.0259(15) Uani 1 1 d . . . C28 C 0.7612(7) 1.0091(6) 1.1206(4) 0.0317(17) Uani 1 1 d . . . N1 N 0.4480(5) 0.6084(4) 0.6222(3) 0.0194(12) Uani 1 1 d . . . N2 N 0.2823(5) 0.3546(4) 0.6259(4) 0.0228(12) Uani 1 1 d . . . N3 N 0.4554(5) 0.8663(5) 0.6158(4) 0.0277(13) Uani 1 1 d . . . N4 N 0.7212(5) 0.9788(5) 0.6323(4) 0.0286(13) Uani 1 1 d . . . N5 N 0.8062(6) 0.9250(4) 1.0926(4) 0.0281(13) Uani 1 1 d . . . N6 N 0.5391(5) 0.8307(5) 1.0520(4) 0.0270(13) Uani 1 1 d . . . O1W O 0.7833(5) 0.6856(4) 0.9887(3) 0.0344(12) Uani 1 1 d D . . H1WA H 0.741(6) 0.617(4) 0.943(4) 0.041 Uiso 1 1 d D . . H1WB H 0.769(6) 0.647(5) 1.038(3) 0.041 Uiso 1 1 d D . . O1 O 0.4728(4) 0.6868(4) 0.4451(3) 0.0320(11) Uani 1 1 d . . . O2 O 0.2946(6) 0.5015(4) 0.3583(3) 0.0581(16) Uani 1 1 d . . . O2W O 0.0470(11) 0.4929(15) 0.0925(9) 0.192(5) Uani 1 1 d D . . H2WA H -0.026(9) 0.474(15) 0.115(11) 0.231 Uiso 1 1 d D . . H2WB H 0.125(7) 0.499(15) 0.114(11) 0.231 Uiso 1 1 d D . . O3 O 0.0836(5) 0.2547(5) 0.4259(4) 0.0653(17) Uani 1 1 d . . . O3W O -0.0021(9) 0.4581(7) 0.3967(7) 0.106(2) Uani 1 1 d D . . H3WA H 0.066(7) 0.448(10) 0.419(8) 0.127 Uiso 1 1 d D . . H3WB H 0.011(12) 0.516(7) 0.445(5) 0.127 Uiso 1 1 d D . . O4 O 0.2643(4) 0.2477(4) 0.3831(3) 0.0312(11) Uani 1 1 d . . . O4W O 0.1562(8) 0.5880(6) 0.7944(5) 0.085(2) Uani 1 1 d D . . H4WA H 0.163(9) 0.526(6) 0.811(7) 0.102 Uiso 1 1 d D . . H4WB H 0.111(9) 0.571(9) 0.734(3) 0.102 Uiso 1 1 d D . . O5 O 0.3933(4) 0.3435(4) 0.8486(3) 0.0292(11) Uani 1 1 d . . . O5W O 0.3192(5) 0.5290(5) 0.1651(4) 0.0428(13) Uani 1 1 d D . . H5WA H 0.402(3) 0.568(6) 0.158(5) 0.051 Uiso 1 1 d D . . H5WB H 0.319(7) 0.528(6) 0.228(2) 0.051 Uiso 1 1 d D . . O6 O 0.2266(4) 0.4005(4) 0.8413(3) 0.0343(11) Uani 1 1 d . . . O7 O 0.5191(4) 0.6328(3) 0.8915(3) 0.0287(11) Uani 1 1 d . . . O8 O 0.6037(4) 0.7838(4) 0.8001(3) 0.0303(11) 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 Cu1 0.0332(5) 0.0219(5) 0.0189(4) 0.0024(4) 0.0034(4) 0.0117(4) Cu2 0.0218(5) 0.0184(4) 0.0280(5) 0.0036(4) 0.0046(4) 0.0072(4) C1 0.021(3) 0.016(3) 0.017(3) -0.002(3) 0.004(3) 0.008(3) C2 0.011(3) 0.019(3) 0.023(4) 0.000(3) 0.003(3) 0.007(3) C3 0.016(3) 0.018(3) 0.023(3) 0.007(3) 0.010(3) 0.011(3) C4 0.020(3) 0.019(3) 0.013(3) -0.004(3) -0.003(3) 0.007(3) C5 0.039(4) 0.026(4) 0.021(4) 0.008(3) 0.009(3) 0.022(3) C6 0.022(4) 0.028(4) 0.027(4) 0.006(3) 0.004(3) 0.008(3) C7 0.028(4) 0.015(3) 0.016(3) -0.002(3) 0.004(3) 0.004(3) C8 0.024(4) 0.029(4) 0.017(3) 0.001(3) 0.002(3) 0.019(3) C9 0.031(4) 0.049(5) 0.048(5) 0.015(4) 0.013(4) 0.024(4) C10 0.046(5) 0.087(7) 0.048(5) 0.030(5) 0.028(4) 0.042(5) C11 0.085(7) 0.095(7) 0.053(6) 0.042(5) 0.035(5) 0.078(6) C12 0.085(7) 0.060(5) 0.039(5) 0.030(4) 0.039(5) 0.053(5) C13 0.070(6) 0.028(4) 0.052(5) 0.012(4) 0.012(5) 0.015(4) C14 0.065(7) 0.027(5) 0.077(7) 0.015(5) 0.002(5) -0.004(5) C15 0.032(5) 0.040(5) 0.070(6) 0.011(5) -0.005(4) -0.007(4) C16 0.030(4) 0.031(4) 0.049(5) 0.014(4) 0.005(4) 0.006(3) C17 0.048(5) 0.027(4) 0.025(4) 0.009(3) 0.013(4) 0.018(4) C18 0.050(5) 0.034(4) 0.024(4) 0.015(3) 0.016(3) 0.030(4) C19 0.036(5) 0.040(4) 0.027(4) 0.009(3) 0.005(4) 0.008(4) C20 0.042(5) 0.055(5) 0.033(5) 0.009(4) 0.001(4) 0.009(4) C21 0.053(6) 0.031(4) 0.036(5) 0.001(4) -0.001(4) -0.008(4) C22 0.069(6) 0.022(4) 0.036(4) -0.001(3) 0.006(4) 0.017(4) C23 0.066(6) 0.031(4) 0.018(4) 0.001(3) 0.002(4) 0.026(4) C24 0.078(6) 0.062(6) 0.025(4) 0.014(4) 0.013(4) 0.057(5) C25 0.042(5) 0.048(5) 0.042(5) 0.021(4) 0.014(4) 0.025(4) C26 0.043(5) 0.038(4) 0.039(5) 0.016(4) 0.005(4) 0.019(4) C27 0.044(4) 0.019(4) 0.015(3) 0.005(3) 0.006(3) 0.015(3) C28 0.053(5) 0.026(4) 0.012(3) 0.009(3) 0.008(3) 0.013(4) N1 0.027(3) 0.016(3) 0.018(3) 0.005(2) 0.007(2) 0.012(2) N2 0.027(3) 0.022(3) 0.019(3) 0.003(2) 0.005(2) 0.012(2) N3 0.029(3) 0.035(3) 0.026(3) 0.011(3) 0.011(3) 0.019(3) N4 0.028(3) 0.024(3) 0.024(3) 0.005(2) 0.003(3) 0.005(3) N5 0.038(4) 0.021(3) 0.017(3) 0.003(2) 0.002(3) 0.009(3) N6 0.030(3) 0.026(3) 0.024(3) 0.008(3) 0.001(3) 0.013(3) O1W 0.035(3) 0.037(3) 0.029(3) 0.010(2) 0.014(2) 0.012(3) O1 0.032(3) 0.029(3) 0.027(3) 0.013(2) 0.006(2) 0.006(2) O2 0.088(4) 0.030(3) 0.021(3) 0.007(2) -0.010(3) 0.004(3) O2W 0.132(9) 0.403(15) 0.142(8) 0.122(9) 0.064(7) 0.185(11) O3 0.019(3) 0.093(4) 0.050(3) -0.032(3) 0.001(3) 0.013(3) O3W 0.099(6) 0.104(6) 0.133(7) 0.009(5) -0.003(6) 0.075(5) O4 0.031(3) 0.042(3) 0.017(2) -0.009(2) -0.003(2) 0.021(2) O4W 0.101(5) 0.066(5) 0.098(5) 0.018(4) 0.000(5) 0.055(4) O5 0.036(3) 0.034(3) 0.027(3) 0.012(2) 0.008(2) 0.022(2) O5W 0.044(3) 0.058(3) 0.026(3) 0.004(3) 0.011(3) 0.025(3) O6 0.034(3) 0.047(3) 0.032(3) 0.020(2) 0.015(2) 0.023(2) O7 0.036(3) 0.020(2) 0.017(2) 0.0034(19) 0.000(2) 0.005(2) O8 0.037(3) 0.014(2) 0.024(3) 0.003(2) 0.005(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O7 1.974(4) . ? Cu1 O1W 1.985(5) . ? Cu1 N6 1.996(5) . ? Cu1 N5 2.030(5) . ? Cu1 O5 2.271(4) 2_667 ? Cu2 O4 1.946(4) 2_666 ? Cu2 N3 2.022(5) . ? Cu2 N4 2.024(5) . ? Cu2 N1 2.093(5) . ? Cu2 O1 2.300(4) . ? C1 N1 1.344(7) . ? C1 C2 1.405(7) . ? C1 C5 1.537(8) . ? C2 N2 1.348(7) . ? C2 C6 1.537(8) . ? C3 N2 1.363(7) . ? C3 C4 1.412(7) . ? C3 C7 1.534(8) . ? C4 N1 1.350(7) . ? C4 C8 1.519(8) . ? C5 O2 1.244(7) . ? C5 O1 1.255(7) . ? C6 O3 1.221(7) . ? C6 O4 1.259(7) . ? C7 O5 1.254(7) . ? C7 O6 1.260(7) . ? C8 O8 1.239(6) . ? C8 O7 1.286(7) . ? C9 N3 1.343(8) . ? C9 C10 1.387(9) . ? C9 H9A 0.9300 . ? C10 C11 1.385(10) . ? C10 H10A 0.9300 . ? C11 C12 1.360(11) . ? C11 H11A 0.9300 . ? C12 C18 1.391(9) . ? C12 H12A 0.9300 . ? C13 C14 1.371(11) . ? C13 C17 1.413(9) . ? C13 H13A 0.9300 . ? C14 C15 1.357(11) . ? C14 H14A 0.9300 . ? C15 C16 1.401(9) . ? C15 H15A 0.9300 . ? C16 N4 1.344(8) . ? C16 H16A 0.9300 . ? C17 N4 1.378(8) . ? C17 C18 1.462(9) . ? C18 N3 1.361(7) . ? C19 N5 1.344(8) . ? C19 C20 1.395(9) . ? C19 H19A 0.9300 . ? C20 C21 1.379(10) . ? C20 H20A 0.9300 . ? C21 C22 1.396(10) . ? C21 H21A 0.9300 . ? C22 C28 1.398(8) . ? C22 H22A 0.9300 . ? C23 C24 1.385(10) . ? C23 C27 1.386(9) . ? C23 H23A 0.9300 . ? C24 C25 1.398(9) . ? C24 H24A 0.9300 . ? C25 C26 1.403(9) . ? C25 H25A 0.9300 . ? C26 N6 1.337(8) . ? C26 H26A 0.9300 . ? C27 N6 1.363(7) . ? C27 C28 1.470(9) . ? C28 N5 1.356(8) . ? O1W H1WA 0.86(2) . ? O1W H1WB 0.85(2) . ? O2W H2WA 0.85(2) . ? O2W H2WB 0.85(2) . ? O3W H3WA 0.85(2) . ? O3W H3WB 0.84(2) . ? O4 Cu2 1.946(4) 2_666 ? O4W H4WA 0.85(2) . ? O4W H4WB 0.85(2) . ? O5 Cu1 2.271(4) 2_667 ? O5W H5WA 0.85(2) . ? O5W H5WB 0.85(2) . ? 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 O7 Cu1 O1W 90.52(18) . . ? O7 Cu1 N6 94.3(2) . . ? O1W Cu1 N6 174.7(2) . . ? O7 Cu1 N5 151.59(18) . . ? O1W Cu1 N5 93.6(2) . . ? N6 Cu1 N5 81.1(2) . . ? O7 Cu1 O5 108.59(16) . 2_667 ? O1W Cu1 O5 93.06(17) . 2_667 ? N6 Cu1 O5 87.36(18) . 2_667 ? N5 Cu1 O5 99.24(17) . 2_667 ? O4 Cu2 N3 169.7(2) 2_666 . ? O4 Cu2 N4 89.6(2) 2_666 . ? N3 Cu2 N4 80.4(2) . . ? O4 Cu2 N1 91.81(18) 2_666 . ? N3 Cu2 N1 97.5(2) . . ? N4 Cu2 N1 168.23(19) . . ? O4 Cu2 O1 97.54(16) 2_666 . ? N3 Cu2 O1 89.07(18) . . ? N4 Cu2 O1 116.11(18) . . ? N1 Cu2 O1 75.28(17) . . ? N1 C1 C2 120.2(5) . . ? N1 C1 C5 115.6(5) . . ? C2 C1 C5 124.2(5) . . ? N2 C2 C1 121.6(5) . . ? N2 C2 C6 115.6(5) . . ? C1 C2 C6 122.7(5) . . ? N2 C3 C4 121.1(5) . . ? N2 C3 C7 113.9(5) . . ? C4 C3 C7 124.9(5) . . ? N1 C4 C3 119.9(5) . . ? N1 C4 C8 116.7(5) . . ? C3 C4 C8 123.4(5) . . ? O2 C5 O1 127.3(6) . . ? O2 C5 C1 116.2(5) . . ? O1 C5 C1 116.4(5) . . ? O3 C6 O4 125.8(6) . . ? O3 C6 C2 114.5(6) . . ? O4 C6 C2 119.7(5) . . ? O5 C7 O6 127.6(6) . . ? O5 C7 C3 118.8(6) . . ? O6 C7 C3 113.4(5) . . ? O8 C8 O7 126.7(6) . . ? O8 C8 C4 119.5(5) . . ? O7 C8 C4 113.7(5) . . ? N3 C9 C10 123.2(7) . . ? N3 C9 H9A 118.4 . . ? C10 C9 H9A 118.4 . . ? C11 C10 C9 117.9(7) . . ? C11 C10 H10A 121.1 . . ? C9 C10 H10A 121.1 . . ? C12 C11 C10 120.2(7) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C18 119.3(8) . . ? C11 C12 H12A 120.4 . . ? C18 C12 H12A 120.4 . . ? C14 C13 C17 120.8(8) . . ? C14 C13 H13A 119.6 . . ? C17 C13 H13A 119.6 . . ? C15 C14 C13 120.0(8) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 118.5(8) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.7 . . ? N4 C16 C15 122.8(7) . . ? N4 C16 H16A 118.6 . . ? C15 C16 H16A 118.6 . . ? N4 C17 C13 118.7(7) . . ? N4 C17 C18 115.2(6) . . ? C13 C17 C18 126.0(7) . . ? N3 C18 C12 121.8(7) . . ? N3 C18 C17 114.4(6) . . ? C12 C18 C17 123.9(7) . . ? N5 C19 C20 122.6(7) . . ? N5 C19 H19A 118.7 . . ? C20 C19 H19A 118.7 . . ? C21 C20 C19 117.8(7) . . ? C21 C20 H20A 121.1 . . ? C19 C20 H20A 121.1 . . ? C20 C21 C22 120.6(7) . . ? C20 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C21 C22 C28 118.3(7) . . ? C21 C22 H22A 120.9 . . ? C28 C22 H22A 120.9 . . ? C24 C23 C27 120.3(6) . . ? C24 C23 H23A 119.8 . . ? C27 C23 H23A 119.8 . . ? C23 C24 C25 120.5(7) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C24 C25 C26 116.4(7) . . ? C24 C25 H25A 121.8 . . ? C26 C25 H25A 121.8 . . ? N6 C26 C25 122.6(7) . . ? N6 C26 H26A 118.7 . . ? C25 C26 H26A 118.7 . . ? N6 C27 C23 119.1(6) . . ? N6 C27 C28 114.9(6) . . ? C23 C27 C28 126.0(6) . . ? N5 C28 C22 121.2(7) . . ? N5 C28 C27 115.0(6) . . ? C22 C28 C27 123.8(7) . . ? C1 N1 C4 119.5(5) . . ? C1 N1 Cu2 117.8(4) . . ? C4 N1 Cu2 122.3(4) . . ? C2 N2 C3 117.6(5) . . ? C9 N3 C18 117.7(6) . . ? C9 N3 Cu2 126.7(5) . . ? C18 N3 Cu2 115.6(4) . . ? C16 N4 C17 119.0(6) . . ? C16 N4 Cu2 126.6(5) . . ? C17 N4 Cu2 114.3(4) . . ? C19 N5 C28 119.4(6) . . ? C19 N5 Cu1 126.6(5) . . ? C28 N5 Cu1 113.8(4) . . ? C26 N6 C27 121.0(6) . . ? C26 N6 Cu1 124.1(5) . . ? C27 N6 Cu1 114.8(4) . . ? Cu1 O1W H1WA 110(5) . . ? Cu1 O1W H1WB 91(4) . . ? H1WA O1W H1WB 93(6) . . ? C5 O1 Cu2 113.8(4) . . ? H2WA O2W H2WB 136(10) . . ? H3WA O3W H3WB 98(10) . . ? C6 O4 Cu2 141.9(4) . 2_666 ? H4WA O4W H4WB 114(9) . . ? C7 O5 Cu1 121.9(4) . 2_667 ? H5WA O5W H5WB 109(7) . . ? C8 O7 Cu1 116.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 3.1(8) . . . . ? C5 C1 C2 N2 -174.8(5) . . . . ? N1 C1 C2 C6 -179.8(5) . . . . ? C5 C1 C2 C6 2.4(9) . . . . ? N2 C3 C4 N1 3.4(8) . . . . ? C7 C3 C4 N1 -172.6(5) . . . . ? N2 C3 C4 C8 -177.6(5) . . . . ? C7 C3 C4 C8 6.4(9) . . . . ? N1 C1 C5 O2 -166.6(6) . . . . ? C2 C1 C5 O2 11.3(9) . . . . ? N1 C1 C5 O1 12.1(8) . . . . ? C2 C1 C5 O1 -170.0(5) . . . . ? N2 C2 C6 O3 72.8(7) . . . . ? C1 C2 C6 O3 -104.5(7) . . . . ? N2 C2 C6 O4 -105.7(6) . . . . ? C1 C2 C6 O4 77.0(7) . . . . ? N2 C3 C7 O5 87.0(7) . . . . ? C4 C3 C7 O5 -96.7(7) . . . . ? N2 C3 C7 O6 -88.5(6) . . . . ? C4 C3 C7 O6 87.7(7) . . . . ? N1 C4 C8 O8 -1.8(8) . . . . ? C3 C4 C8 O8 179.1(5) . . . . ? N1 C4 C8 O7 -179.6(5) . . . . ? C3 C4 C8 O7 1.4(8) . . . . ? N3 C9 C10 C11 -0.7(11) . . . . ? C9 C10 C11 C12 1.3(11) . . . . ? C10 C11 C12 C18 -1.2(11) . . . . ? C17 C13 C14 C15 -1.0(13) . . . . ? C13 C14 C15 C16 -0.1(13) . . . . ? C14 C15 C16 N4 -0.1(12) . . . . ? C14 C13 C17 N4 2.4(10) . . . . ? C14 C13 C17 C18 -178.7(7) . . . . ? C11 C12 C18 N3 0.5(10) . . . . ? C11 C12 C18 C17 179.1(6) . . . . ? N4 C17 C18 N3 2.3(8) . . . . ? C13 C17 C18 N3 -176.6(6) . . . . ? N4 C17 C18 C12 -176.4(6) . . . . ? C13 C17 C18 C12 4.7(11) . . . . ? N5 C19 C20 C21 -1.9(10) . . . . ? C19 C20 C21 C22 1.7(11) . . . . ? C20 C21 C22 C28 0.4(10) . . . . ? C27 C23 C24 C25 1.2(10) . . . . ? C23 C24 C25 C26 -2.3(10) . . . . ? C24 C25 C26 N6 1.8(10) . . . . ? C24 C23 C27 N6 0.6(9) . . . . ? C24 C23 C27 C28 -177.5(6) . . . . ? C21 C22 C28 N5 -2.6(9) . . . . ? C21 C22 C28 C27 178.0(6) . . . . ? N6 C27 C28 N5 -4.8(7) . . . . ? C23 C27 C28 N5 173.4(6) . . . . ? N6 C27 C28 C22 174.7(6) . . . . ? C23 C27 C28 C22 -7.1(10) . . . . ? C2 C1 N1 C4 -1.5(8) . . . . ? C5 C1 N1 C4 176.5(5) . . . . ? C2 C1 N1 Cu2 172.2(4) . . . . ? C5 C1 N1 Cu2 -9.8(6) . . . . ? C3 C4 N1 C1 -1.6(8) . . . . ? C8 C4 N1 C1 179.3(5) . . . . ? C3 C4 N1 Cu2 -175.0(4) . . . . ? C8 C4 N1 Cu2 6.0(7) . . . . ? O4 Cu2 N1 C1 -92.9(4) 2_666 . . . ? N3 Cu2 N1 C1 91.5(4) . . . . ? N4 Cu2 N1 C1 170.4(9) . . . . ? O1 Cu2 N1 C1 4.4(4) . . . . ? O4 Cu2 N1 C4 80.6(4) 2_666 . . . ? N3 Cu2 N1 C4 -95.0(4) . . . . ? N4 Cu2 N1 C4 -16.1(12) . . . . ? O1 Cu2 N1 C4 177.9(5) . . . . ? C1 C2 N2 C3 -1.3(8) . . . . ? C6 C2 N2 C3 -178.6(5) . . . . ? C4 C3 N2 C2 -1.9(8) . . . . ? C7 C3 N2 C2 174.5(5) . . . . ? C10 C9 N3 C18 0.1(10) . . . . ? C10 C9 N3 Cu2 -177.5(5) . . . . ? C12 C18 N3 C9 0.0(9) . . . . ? C17 C18 N3 C9 -178.7(6) . . . . ? C12 C18 N3 Cu2 177.8(5) . . . . ? C17 C18 N3 Cu2 -0.9(7) . . . . ? O4 Cu2 N3 C9 -169.2(9) 2_666 . . . ? N4 Cu2 N3 C9 177.2(6) . . . . ? N1 Cu2 N3 C9 -14.5(5) . . . . ? O1 Cu2 N3 C9 60.5(5) . . . . ? O4 Cu2 N3 C18 13.2(13) 2_666 . . . ? N4 Cu2 N3 C18 -0.4(4) . . . . ? N1 Cu2 N3 C18 167.9(4) . . . . ? O1 Cu2 N3 C18 -117.1(4) . . . . ? C15 C16 N4 C17 1.6(10) . . . . ? C15 C16 N4 Cu2 -177.3(5) . . . . ? C13 C17 N4 C16 -2.6(9) . . . . ? C18 C17 N4 C16 178.4(6) . . . . ? C13 C17 N4 Cu2 176.4(5) . . . . ? C18 C17 N4 Cu2 -2.6(7) . . . . ? O4 Cu2 N4 C16 3.0(5) 2_666 . . . ? N3 Cu2 N4 C16 -179.4(6) . . . . ? N1 Cu2 N4 C16 99.9(11) . . . . ? O1 Cu2 N4 C16 -95.2(5) . . . . ? O4 Cu2 N4 C17 -176.0(4) 2_666 . . . ? N3 Cu2 N4 C17 1.6(4) . . . . ? N1 Cu2 N4 C17 -79.1(11) . . . . ? O1 Cu2 N4 C17 85.8(4) . . . . ? C20 C19 N5 C28 -0.2(9) . . . . ? C20 C19 N5 Cu1 174.1(5) . . . . ? C22 C28 N5 C19 2.5(9) . . . . ? C27 C28 N5 C19 -178.0(5) . . . . ? C22 C28 N5 Cu1 -172.5(5) . . . . ? C27 C28 N5 Cu1 7.0(6) . . . . ? O7 Cu1 N5 C19 -97.4(6) . . . . ? O1W Cu1 N5 C19 0.5(5) . . . . ? N6 Cu1 N5 C19 -180.0(5) . . . . ? O5 Cu1 N5 C19 94.2(5) 2_667 . . . ? O7 Cu1 N5 C28 77.2(6) . . . . ? O1W Cu1 N5 C28 175.0(4) . . . . ? N6 Cu1 N5 C28 -5.4(4) . . . . ? O5 Cu1 N5 C28 -91.3(4) 2_667 . . . ? C25 C26 N6 C27 0.0(9) . . . . ? C25 C26 N6 Cu1 176.7(5) . . . . ? C23 C27 N6 C26 -1.2(9) . . . . ? C28 C27 N6 C26 177.1(5) . . . . ? C23 C27 N6 Cu1 -178.2(4) . . . . ? C28 C27 N6 Cu1 0.1(6) . . . . ? O7 Cu1 N6 C26 34.1(5) . . . . ? O1W Cu1 N6 C26 -169.0(19) . . . . ? N5 Cu1 N6 C26 -174.1(5) . . . . ? O5 Cu1 N6 C26 -74.3(5) 2_667 . . . ? O7 Cu1 N6 C27 -149.0(4) . . . . ? O1W Cu1 N6 C27 8(2) . . . . ? N5 Cu1 N6 C27 2.8(4) . . . . ? O5 Cu1 N6 C27 102.6(4) 2_667 . . . ? O2 C5 O1 Cu2 170.5(6) . . . . ? C1 C5 O1 Cu2 -8.0(6) . . . . ? O4 Cu2 O1 C5 92.3(4) 2_666 . . . ? N3 Cu2 O1 C5 -95.5(4) . . . . ? N4 Cu2 O1 C5 -174.4(4) . . . . ? N1 Cu2 O1 C5 2.4(4) . . . . ? O3 C6 O4 Cu2 -143.6(6) . . . 2_666 ? C2 C6 O4 Cu2 34.7(10) . . . 2_666 ? O6 C7 O5 Cu1 0.6(8) . . . 2_667 ? C3 C7 O5 Cu1 -174.3(3) . . . 2_667 ? O8 C8 O7 Cu1 -8.7(8) . . . . ? C4 C8 O7 Cu1 168.8(3) . . . . ? O1W Cu1 O7 C8 -88.9(4) . . . . ? N6 Cu1 O7 C8 89.0(4) . . . . ? N5 Cu1 O7 C8 9.7(7) . . . . ? O5 Cu1 O7 C8 177.7(4) 2_667 . . . ? 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 O1W H1WA O5W 0.86(2) 1.91(2) 2.758(7) 169(7) 2_666 O1W H1WB O6 0.85(2) 1.80(2) 2.637(6) 167(6) 2_667 O1W H1WB O5 0.85(2) 2.55(5) 3.095(6) 122(5) 2_667 O2W H2WA O4W 0.85(2) 1.98(6) 2.785(12) 158(15) 2_566 O2W H2WB O5W 0.85(2) 2.03(3) 2.883(10) 175(15) . O3W H3WA O3 0.85(2) 2.44(8) 3.067(9) 131(9) . O3W H3WA O2 0.85(2) 2.61(8) 3.242(10) 132(10) . O3W H3WB O3W 0.84(2) 2.14(6) 2.824(18) 139(9) 2_566 O4W H4WA O6 0.85(2) 2.00(3) 2.831(7) 165(9) . O4W H4WB O3W 0.85(2) 1.89(2) 2.740(10) 175(10) 2_566 O5W H5WA O5 0.85(2) 2.06(2) 2.915(6) 175(7) 2_666 O5W H5WB O2 0.85(2) 1.86(2) 2.707(6) 171(7) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.650 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.100 # Attachment 'complex 2.cif' data_r070927e _database_code_depnum_ccdc_archive 'CCDC 666545' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N5 O10 Zn' _chemical_formula_weight 659.92 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.951(2) _cell_length_b 19.019(4) _cell_length_c 26.714(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5564.0(19) _cell_formula_units_Z 8 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 8823 _cell_measurement_theta_min 1.524 _cell_measurement_theta_max 27.904 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2728 _exptl_absorpt_coefficient_mu 0.952 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9451 _exptl_absorpt_correction_T_max 0.9629 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_number 32657 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4899 _reflns_number_gt 4171 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0524P)^2^+5.3223P] 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 4899 _refine_ls_number_parameters 397 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.128 _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 Zn1 Zn 0.67533(4) 0.02392(2) 0.383417(15) 0.01743(15) Uani 1 1 d . . . O1 O 0.5462(2) 0.18199(13) 0.46991(10) 0.0285(6) Uani 1 1 d . . . O2 O 0.7218(2) 0.14241(13) 0.50275(9) 0.0246(6) Uani 1 1 d . . . O3 O 0.5652(2) -0.06293(13) 0.37539(9) 0.0210(6) Uani 1 1 d . . . O4 O 0.4516(3) -0.14340(14) 0.41339(10) 0.0300(7) Uani 1 1 d . . . N1 N 0.5586(3) 0.02152(15) 0.45639(10) 0.0161(6) Uani 1 1 d . . . N2 N 0.8173(3) -0.04003(15) 0.41559(11) 0.0179(7) Uani 1 1 d . . . N3 N 0.8064(3) 0.10043(15) 0.40168(10) 0.0168(6) Uani 1 1 d . . . N4 N 0.5562(3) 0.08680(15) 0.33985(11) 0.0191(7) Uani 1 1 d . . . N5 N 0.7411(3) 0.00195(15) 0.30810(11) 0.0183(6) Uani 1 1 d . . . C1 C 0.6131(3) 0.13683(19) 0.49019(13) 0.0186(8) Uani 1 1 d . . . C2 C 0.5548(3) 0.06437(18) 0.49661(13) 0.0170(7) Uani 1 1 d . . . C3 C 0.5038(3) -0.04160(17) 0.45958(13) 0.0157(7) Uani 1 1 d . . . C4 C 0.5065(3) -0.08673(18) 0.41251(13) 0.0186(8) Uani 1 1 d . . . C5 C 0.8228(4) -0.1095(2) 0.42043(14) 0.0253(9) Uani 1 1 d . . . H5 H 0.7530 -0.1356 0.4135 0.030 Uiso 1 1 calc R . . C6 C 0.9271(4) -0.1453(2) 0.43528(15) 0.0277(9) Uani 1 1 d . . . H6 H 0.9266 -0.1940 0.4384 0.033 Uiso 1 1 calc R . . C7 C 1.0314(4) -0.1073(2) 0.44531(14) 0.0258(9) Uani 1 1 d . . . H7 H 1.1026 -0.1302 0.4551 0.031 Uiso 1 1 calc R . . C8 C 1.0293(3) -0.0336(2) 0.44068(13) 0.0205(8) Uani 1 1 d . . . C9 C 1.1325(4) 0.0104(2) 0.45166(13) 0.0235(8) Uani 1 1 d . . . H9 H 1.2056 -0.0102 0.4616 0.028 Uiso 1 1 calc R . . C10 C 1.1257(3) 0.0815(2) 0.44782(13) 0.0237(8) Uani 1 1 d . . . H10 H 1.1933 0.1088 0.4558 0.028 Uiso 1 1 calc R . . C11 C 1.0147(3) 0.11478(19) 0.43156(13) 0.0199(8) Uani 1 1 d . . . C12 C 1.0023(4) 0.1880(2) 0.42475(14) 0.0242(9) Uani 1 1 d . . . H12 H 1.0666 0.2180 0.4327 0.029 Uiso 1 1 calc R . . C13 C 0.8959(3) 0.21441(19) 0.40654(14) 0.0234(8) Uani 1 1 d . . . H13 H 0.8876 0.2626 0.4018 0.028 Uiso 1 1 calc R . . C14 C 0.7991(3) 0.16957(19) 0.39488(13) 0.0211(8) Uani 1 1 d . . . H14 H 0.7274 0.1886 0.3820 0.025 Uiso 1 1 calc R . . C15 C 0.9123(3) 0.07289(19) 0.41955(13) 0.0179(8) Uani 1 1 d . . . C16 C 0.9192(3) -0.00218(19) 0.42539(12) 0.0169(8) Uani 1 1 d . . . C17 C 0.4662(3) 0.1276(2) 0.35580(15) 0.0238(8) Uani 1 1 d . . . H17 H 0.4561 0.1341 0.3901 0.029 Uiso 1 1 calc R . . C18 C 0.3854(4) 0.1614(2) 0.32276(15) 0.0269(9) Uani 1 1 d . . . H18 H 0.3219 0.1888 0.3351 0.032 Uiso 1 1 calc R . . C19 C 0.4011(4) 0.1536(2) 0.27228(15) 0.0260(9) Uani 1 1 d . . . H19 H 0.3491 0.1765 0.2501 0.031 Uiso 1 1 calc R . . C20 C 0.4958(3) 0.11102(18) 0.25411(13) 0.0212(8) Uani 1 1 d . . . C21 C 0.5176(4) 0.0989(2) 0.20209(14) 0.0276(9) Uani 1 1 d . . . H21 H 0.4692 0.1217 0.1785 0.033 Uiso 1 1 calc R . . C22 C 0.6071(4) 0.0552(2) 0.18627(14) 0.0265(9) Uani 1 1 d . . . H22 H 0.6177 0.0474 0.1522 0.032 Uiso 1 1 calc R . . C23 C 0.6852(3) 0.02090(19) 0.22124(14) 0.0208(8) Uani 1 1 d . . . C24 C 0.7799(4) -0.0244(2) 0.20651(14) 0.0262(9) Uani 1 1 d . . . H24 H 0.7929 -0.0339 0.1728 0.031 Uiso 1 1 calc R . . C25 C 0.8527(4) -0.0544(2) 0.24216(15) 0.0271(9) Uani 1 1 d . . . H25 H 0.9164 -0.0841 0.2330 0.033 Uiso 1 1 calc R . . C26 C 0.8299(3) -0.03978(19) 0.29266(14) 0.0205(8) Uani 1 1 d . . . H26 H 0.8798 -0.0605 0.3166 0.025 Uiso 1 1 calc R . . C27 C 0.6687(3) 0.03242(18) 0.27253(13) 0.0179(8) Uani 1 1 d . . . C28 C 0.5716(3) 0.07769(18) 0.28958(13) 0.0190(8) Uani 1 1 d . . . O5 O 0.3074(2) 0.22700(15) 0.46235(11) 0.0340(7) Uani 1 1 d D . . H5A H 0.2857 0.2622 0.4803 0.041 Uiso 1 1 d RD . . H5B H 0.3799 0.2117 0.4692 0.041 Uiso 1 1 d RD . . O6 O 0.6089(2) 0.83693(14) 0.29802(10) 0.0284(6) Uani 1 1 d D . . H6A H 0.5899 0.8648 0.3219 0.034 Uiso 1 1 d RD . . H6B H 0.6499 0.8536 0.2742 0.034 Uiso 1 1 d RD . . O7 O 0.0504(2) 0.84761(15) 0.30964(11) 0.0336(7) Uani 1 1 d D . . H7A H 0.1053 0.8397 0.3317 0.040 Uiso 1 1 d RD . . H7B H 0.0750 0.8499 0.2795 0.040 Uiso 1 1 d RD . . O8 O 0.2389(3) 0.80316(15) 0.37543(10) 0.0329(7) Uani 1 1 d D . . H8A H 0.2164 0.7778 0.4004 0.039 Uiso 1 1 d RD . . H8B H 0.3056 0.8262 0.3808 0.039 Uiso 1 1 d RD . . O9 O 0.6673(3) 0.26494(16) 0.30108(11) 0.0355(7) Uani 1 1 d D . . H9A H 0.6015 0.2861 0.3088 0.043 Uiso 1 1 d RD . . H9B H 0.7321 0.2895 0.3019 0.043 Uiso 1 1 d RD . . O10 O 0.5964(3) 0.25643(15) 0.20090(11) 0.0349(7) Uani 1 1 d D . . H10A H 0.6365 0.2654 0.1739 0.042 Uiso 1 1 d RD . . H10B H 0.6399 0.2569 0.2275 0.042 Uiso 1 1 d RD . . 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 Zn1 0.0182(3) 0.0174(2) 0.0167(2) 0.00121(16) -0.00092(16) -0.00036(17) O1 0.0305(16) 0.0200(14) 0.0351(16) 0.0047(12) -0.0042(12) -0.0004(12) O2 0.0194(15) 0.0264(14) 0.0280(15) -0.0022(12) -0.0007(11) -0.0036(11) O3 0.0222(15) 0.0238(14) 0.0171(13) -0.0032(11) 0.0028(10) -0.0039(11) O4 0.0349(17) 0.0247(15) 0.0303(16) -0.0066(12) 0.0082(12) -0.0111(13) N1 0.0144(16) 0.0167(15) 0.0172(16) 0.0013(12) -0.0008(12) 0.0014(12) N2 0.0205(17) 0.0161(15) 0.0172(16) -0.0002(12) -0.0007(12) 0.0002(12) N3 0.0189(16) 0.0165(15) 0.0150(15) 0.0000(12) 0.0013(12) 0.0008(13) N4 0.0186(17) 0.0209(16) 0.0178(16) -0.0002(13) 0.0001(12) -0.0009(13) N5 0.0181(17) 0.0159(15) 0.0210(16) -0.0006(13) 0.0018(12) -0.0009(13) C1 0.017(2) 0.0218(19) 0.0168(18) -0.0002(15) 0.0033(14) -0.0006(16) C2 0.0144(19) 0.0167(17) 0.0200(19) -0.0006(15) -0.0038(14) 0.0027(14) C3 0.0113(18) 0.0151(17) 0.0208(19) 0.0005(14) -0.0012(14) 0.0008(14) C4 0.0177(19) 0.0191(19) 0.0191(19) -0.0021(15) 0.0003(15) -0.0007(15) C5 0.031(2) 0.0196(19) 0.025(2) 0.0018(16) -0.0014(16) 0.0010(17) C6 0.035(2) 0.0190(19) 0.029(2) 0.0010(17) 0.0000(18) 0.0042(18) C7 0.029(2) 0.029(2) 0.019(2) 0.0010(17) -0.0018(16) 0.0085(18) C8 0.019(2) 0.027(2) 0.0151(18) 0.0014(15) 0.0026(14) 0.0031(16) C9 0.020(2) 0.034(2) 0.0166(19) 0.0014(16) -0.0018(15) 0.0032(17) C10 0.016(2) 0.034(2) 0.020(2) -0.0026(17) 0.0005(15) -0.0022(17) C11 0.020(2) 0.025(2) 0.0143(18) -0.0014(15) 0.0027(14) -0.0045(16) C12 0.026(2) 0.024(2) 0.022(2) -0.0043(16) 0.0033(16) -0.0092(17) C13 0.029(2) 0.0162(18) 0.025(2) -0.0007(15) -0.0004(16) -0.0014(16) C14 0.024(2) 0.0219(19) 0.0171(19) 0.0001(15) 0.0032(15) 0.0041(16) C15 0.019(2) 0.0198(18) 0.0153(18) -0.0003(14) 0.0037(14) 0.0037(15) C16 0.021(2) 0.0195(18) 0.0100(17) 0.0013(14) 0.0007(14) 0.0002(15) C17 0.021(2) 0.0225(19) 0.028(2) -0.0062(16) -0.0018(16) 0.0047(16) C18 0.021(2) 0.026(2) 0.034(2) -0.0056(17) -0.0044(17) 0.0066(17) C19 0.026(2) 0.022(2) 0.030(2) 0.0015(17) -0.0079(17) 0.0011(17) C20 0.024(2) 0.0180(18) 0.022(2) 0.0014(15) -0.0051(15) 0.0010(16) C21 0.034(2) 0.027(2) 0.022(2) 0.0066(17) -0.0090(17) -0.0031(18) C22 0.034(2) 0.028(2) 0.018(2) -0.0014(16) -0.0026(17) -0.0021(18) C23 0.023(2) 0.0194(19) 0.019(2) -0.0005(15) -0.0010(15) -0.0050(16) C24 0.032(2) 0.029(2) 0.017(2) -0.0048(16) 0.0078(16) -0.0055(18) C25 0.028(2) 0.023(2) 0.030(2) -0.0034(17) 0.0057(17) 0.0016(17) C26 0.017(2) 0.0211(19) 0.023(2) -0.0004(15) -0.0008(15) -0.0022(15) C27 0.019(2) 0.0179(18) 0.0168(19) -0.0002(14) -0.0008(14) -0.0041(15) C28 0.024(2) 0.0156(17) 0.0176(19) 0.0006(15) 0.0007(14) -0.0022(15) O5 0.0255(16) 0.0296(16) 0.0470(19) -0.0099(14) -0.0042(13) 0.0045(12) O6 0.0306(16) 0.0320(15) 0.0224(14) -0.0050(12) 0.0092(11) -0.0009(13) O7 0.0287(16) 0.0402(17) 0.0317(17) 0.0042(13) -0.0028(12) 0.0025(13) O8 0.0287(17) 0.0407(17) 0.0294(16) -0.0034(13) -0.0031(12) -0.0041(14) O9 0.0248(17) 0.0368(17) 0.0449(19) 0.0065(14) -0.0025(13) -0.0007(13) O10 0.0400(18) 0.0327(16) 0.0320(17) 0.0039(13) 0.0030(13) 0.0014(14) _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 Zn1 O3 2.057(2) . ? Zn1 N3 2.102(3) . ? Zn1 N4 2.118(3) . ? Zn1 N2 2.153(3) . ? Zn1 N5 2.177(3) . ? Zn1 N1 2.332(3) . ? O1 C1 1.252(4) . ? O2 C1 1.242(4) . ? O3 C4 1.265(4) . ? O4 C4 1.234(4) . ? N1 C3 1.345(4) . ? N1 C2 1.349(4) . ? N2 C5 1.329(5) . ? N2 C16 1.353(5) . ? N3 C14 1.330(5) . ? N3 C15 1.359(4) . ? N4 C17 1.324(5) . ? N4 C28 1.365(4) . ? N5 C26 1.321(5) . ? N5 C27 1.366(5) . ? C1 C2 1.529(5) . ? C2 C3 1.403(5) 5_656 ? C3 C2 1.403(5) 5_656 ? C3 C4 1.523(5) . ? C5 C6 1.387(5) . ? C5 H5 0.9300 . ? C6 C7 1.379(6) . ? C6 H6 0.9300 . ? C7 C8 1.408(5) . ? C7 H7 0.9300 . ? C8 C16 1.407(5) . ? C8 C9 1.436(5) . ? C9 C10 1.357(5) . ? C9 H9 0.9300 . ? C10 C11 1.437(5) . ? C10 H10 0.9300 . ? C11 C12 1.412(5) . ? C11 C15 1.413(5) . ? C12 C13 1.359(5) . ? C12 H12 0.9300 . ? C13 C14 1.396(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.438(5) . ? C17 C18 1.406(5) . ? C17 H17 0.9300 . ? C18 C19 1.367(6) . ? C18 H18 0.9300 . ? C19 C20 1.403(5) . ? C19 H19 0.9300 . ? C20 C28 1.411(5) . ? C20 C21 1.429(5) . ? C21 C22 1.353(6) . ? C21 H21 0.9300 . ? C22 C23 1.425(5) . ? C22 H22 0.9300 . ? C23 C27 1.399(5) . ? C23 C24 1.405(5) . ? C24 C25 1.367(6) . ? C24 H24 0.9300 . ? C25 C26 1.400(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.442(5) . ? O5 H5A 0.8575 . ? O5 H5B 0.8644 . ? O6 H6A 0.8549 . ? O6 H6B 0.8399 . ? O7 H7A 0.8547 . ? O7 H7B 0.8501 . ? O8 H8A 0.8591 . ? O8 H8B 0.8638 . ? O9 H9A 0.8512 . ? O9 H9B 0.8498 . ? O10 H10A 0.8608 . ? O10 H10B 0.8549 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 N3 168.82(11) . . ? O3 Zn1 N4 91.99(11) . . ? N3 Zn1 N4 99.06(11) . . ? O3 Zn1 N2 90.66(11) . . ? N3 Zn1 N2 78.76(11) . . ? N4 Zn1 N2 169.44(11) . . ? O3 Zn1 N5 86.76(10) . . ? N3 Zn1 N5 96.98(11) . . ? N4 Zn1 N5 78.72(11) . . ? N2 Zn1 N5 91.24(11) . . ? O3 Zn1 N1 75.51(10) . . ? N3 Zn1 N1 101.19(10) . . ? N4 Zn1 N1 97.63(11) . . ? N2 Zn1 N1 92.93(11) . . ? N5 Zn1 N1 161.82(11) . . ? C4 O3 Zn1 120.2(2) . . ? C3 N1 C2 118.3(3) . . ? C3 N1 Zn1 108.4(2) . . ? C2 N1 Zn1 132.2(2) . . ? C5 N2 C16 118.2(3) . . ? C5 N2 Zn1 129.3(3) . . ? C16 N2 Zn1 111.8(2) . . ? C14 N3 C15 118.7(3) . . ? C14 N3 Zn1 127.7(3) . . ? C15 N3 Zn1 113.4(2) . . ? C17 N4 C28 118.9(3) . . ? C17 N4 Zn1 127.7(3) . . ? C28 N4 Zn1 113.1(2) . . ? C26 N5 C27 117.7(3) . . ? C26 N5 Zn1 130.3(2) . . ? C27 N5 Zn1 111.7(2) . . ? O2 C1 O1 128.3(3) . . ? O2 C1 C2 116.6(3) . . ? O1 C1 C2 115.0(3) . . ? N1 C2 C3 119.5(3) . 5_656 ? N1 C2 C1 116.2(3) . . ? C3 C2 C1 124.3(3) 5_656 . ? N1 C3 C2 122.2(3) . 5_656 ? N1 C3 C4 116.2(3) . . ? C2 C3 C4 121.6(3) 5_656 . ? O4 C4 O3 125.1(3) . . ? O4 C4 C3 117.8(3) . . ? O3 C4 C3 117.1(3) . . ? N2 C5 C6 123.6(4) . . ? N2 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C7 C6 C5 118.7(4) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 119.5(4) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C16 C8 C7 117.5(3) . . ? C16 C8 C9 119.1(3) . . ? C7 C8 C9 123.3(3) . . ? C10 C9 C8 121.4(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 120.6(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C15 116.8(3) . . ? C12 C11 C10 123.7(3) . . ? C15 C11 C10 119.4(3) . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? N3 C14 C13 121.8(3) . . ? N3 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? N3 C15 C11 122.7(3) . . ? N3 C15 C16 117.7(3) . . ? C11 C15 C16 119.6(3) . . ? N2 C16 C8 122.5(3) . . ? N2 C16 C15 117.6(3) . . ? C8 C16 C15 119.9(3) . . ? N4 C17 C18 122.3(4) . . ? N4 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 119.4(4) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 119.8(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C28 117.6(3) . . ? C19 C20 C21 123.6(3) . . ? C28 C20 C21 118.8(3) . . ? C22 C21 C20 121.6(4) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C21 C22 C23 120.8(4) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C27 C23 C24 117.8(3) . . ? C27 C23 C22 119.5(3) . . ? C24 C23 C22 122.7(3) . . ? C25 C24 C23 119.4(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 118.9(4) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? N5 C26 C25 123.5(4) . . ? N5 C26 H26 118.2 . . ? C25 C26 H26 118.2 . . ? N5 C27 C23 122.7(3) . . ? N5 C27 C28 117.5(3) . . ? C23 C27 C28 119.9(3) . . ? N4 C28 C20 122.1(3) . . ? N4 C28 C27 118.5(3) . . ? C20 C28 C27 119.4(3) . . ? H5A O5 H5B 113.5 . . ? H6A O6 H6B 117.5 . . ? H7A O7 H7B 116.0 . . ? H8A O8 H8B 113.4 . . ? H9A O9 H9B 116.2 . . ? H10A O10 H10B 114.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Zn1 O3 C4 61.0(6) . . . . ? N4 Zn1 O3 C4 -110.5(3) . . . . ? N2 Zn1 O3 C4 79.7(3) . . . . ? N5 Zn1 O3 C4 170.9(3) . . . . ? N1 Zn1 O3 C4 -13.1(3) . . . . ? O3 Zn1 N1 C3 13.6(2) . . . . ? N3 Zn1 N1 C3 -155.5(2) . . . . ? N4 Zn1 N1 C3 103.6(2) . . . . ? N2 Zn1 N1 C3 -76.4(2) . . . . ? N5 Zn1 N1 C3 26.6(5) . . . . ? O3 Zn1 N1 C2 -179.2(3) . . . . ? N3 Zn1 N1 C2 11.8(3) . . . . ? N4 Zn1 N1 C2 -89.1(3) . . . . ? N2 Zn1 N1 C2 90.9(3) . . . . ? N5 Zn1 N1 C2 -166.1(3) . . . . ? O3 Zn1 N2 C5 6.4(3) . . . . ? N3 Zn1 N2 C5 -177.2(3) . . . . ? N4 Zn1 N2 C5 -98.1(7) . . . . ? N5 Zn1 N2 C5 -80.4(3) . . . . ? N1 Zn1 N2 C5 81.9(3) . . . . ? O3 Zn1 N2 C16 176.8(2) . . . . ? N3 Zn1 N2 C16 -6.9(2) . . . . ? N4 Zn1 N2 C16 72.2(7) . . . . ? N5 Zn1 N2 C16 90.0(2) . . . . ? N1 Zn1 N2 C16 -107.7(2) . . . . ? O3 Zn1 N3 C14 -160.3(5) . . . . ? N4 Zn1 N3 C14 11.1(3) . . . . ? N2 Zn1 N3 C14 -179.4(3) . . . . ? N5 Zn1 N3 C14 90.7(3) . . . . ? N1 Zn1 N3 C14 -88.7(3) . . . . ? O3 Zn1 N3 C15 24.1(7) . . . . ? N4 Zn1 N3 C15 -164.6(2) . . . . ? N2 Zn1 N3 C15 4.9(2) . . . . ? N5 Zn1 N3 C15 -85.0(2) . . . . ? N1 Zn1 N3 C15 95.7(2) . . . . ? O3 Zn1 N4 C17 93.4(3) . . . . ? N3 Zn1 N4 C17 -85.0(3) . . . . ? N2 Zn1 N4 C17 -162.2(5) . . . . ? N5 Zn1 N4 C17 179.7(3) . . . . ? N1 Zn1 N4 C17 17.7(3) . . . . ? O3 Zn1 N4 C28 -80.9(2) . . . . ? N3 Zn1 N4 C28 100.8(2) . . . . ? N2 Zn1 N4 C28 23.6(7) . . . . ? N5 Zn1 N4 C28 5.4(2) . . . . ? N1 Zn1 N4 C28 -156.5(2) . . . . ? O3 Zn1 N5 C26 -86.5(3) . . . . ? N3 Zn1 N5 C26 83.0(3) . . . . ? N4 Zn1 N5 C26 -179.1(3) . . . . ? N2 Zn1 N5 C26 4.1(3) . . . . ? N1 Zn1 N5 C26 -99.1(4) . . . . ? O3 Zn1 N5 C27 86.8(2) . . . . ? N3 Zn1 N5 C27 -103.8(2) . . . . ? N4 Zn1 N5 C27 -5.9(2) . . . . ? N2 Zn1 N5 C27 177.4(2) . . . . ? N1 Zn1 N5 C27 74.1(4) . . . . ? C3 N1 C2 C3 1.1(5) . . . 5_656 ? Zn1 N1 C2 C3 -165.1(2) . . . 5_656 ? C3 N1 C2 C1 -177.2(3) . . . . ? Zn1 N1 C2 C1 16.6(4) . . . . ? O2 C1 C2 N1 -92.8(4) . . . . ? O1 C1 C2 N1 83.0(4) . . . . ? O2 C1 C2 C3 89.0(4) . . . 5_656 ? O1 C1 C2 C3 -95.2(4) . . . 5_656 ? C2 N1 C3 C2 -1.2(5) . . . 5_656 ? Zn1 N1 C3 C2 168.2(3) . . . 5_656 ? C2 N1 C3 C4 177.7(3) . . . . ? Zn1 N1 C3 C4 -13.0(3) . . . . ? Zn1 O3 C4 O4 -169.7(3) . . . . ? Zn1 O3 C4 C3 10.4(4) . . . . ? N1 C3 C4 O4 -176.4(3) . . . . ? C2 C3 C4 O4 2.5(5) 5_656 . . . ? N1 C3 C4 O3 3.6(5) . . . . ? C2 C3 C4 O3 -177.6(3) 5_656 . . . ? C16 N2 C5 C6 0.4(6) . . . . ? Zn1 N2 C5 C6 170.3(3) . . . . ? N2 C5 C6 C7 -0.5(6) . . . . ? C5 C6 C7 C8 0.5(6) . . . . ? C6 C7 C8 C16 -0.5(5) . . . . ? C6 C7 C8 C9 178.2(3) . . . . ? C16 C8 C9 C10 0.3(5) . . . . ? C7 C8 C9 C10 -178.4(4) . . . . ? C8 C9 C10 C11 -1.2(5) . . . . ? C9 C10 C11 C12 -177.4(3) . . . . ? C9 C10 C11 C15 0.0(5) . . . . ? C15 C11 C12 C13 -1.2(5) . . . . ? C10 C11 C12 C13 176.3(3) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? C15 N3 C14 C13 -1.3(5) . . . . ? Zn1 N3 C14 C13 -176.8(3) . . . . ? C12 C13 C14 N3 0.9(6) . . . . ? C14 N3 C15 C11 0.5(5) . . . . ? Zn1 N3 C15 C11 176.5(3) . . . . ? C14 N3 C15 C16 -178.4(3) . . . . ? Zn1 N3 C15 C16 -2.4(4) . . . . ? C12 C11 C15 N3 0.7(5) . . . . ? C10 C11 C15 N3 -176.8(3) . . . . ? C12 C11 C15 C16 179.7(3) . . . . ? C10 C11 C15 C16 2.1(5) . . . . ? C5 N2 C16 C8 -0.4(5) . . . . ? Zn1 N2 C16 C8 -172.0(3) . . . . ? C5 N2 C16 C15 179.4(3) . . . . ? Zn1 N2 C16 C15 7.9(4) . . . . ? C7 C8 C16 N2 0.5(5) . . . . ? C9 C8 C16 N2 -178.3(3) . . . . ? C7 C8 C16 C15 -179.4(3) . . . . ? C9 C8 C16 C15 1.8(5) . . . . ? N3 C15 C16 N2 -3.9(5) . . . . ? C11 C15 C16 N2 177.1(3) . . . . ? N3 C15 C16 C8 175.9(3) . . . . ? C11 C15 C16 C8 -3.0(5) . . . . ? C28 N4 C17 C18 0.5(5) . . . . ? Zn1 N4 C17 C18 -173.4(3) . . . . ? N4 C17 C18 C19 -1.5(6) . . . . ? C17 C18 C19 C20 1.2(6) . . . . ? C18 C19 C20 C28 0.0(5) . . . . ? C18 C19 C20 C21 178.9(4) . . . . ? C19 C20 C21 C22 -177.3(4) . . . . ? C28 C20 C21 C22 1.6(6) . . . . ? C20 C21 C22 C23 -1.7(6) . . . . ? C21 C22 C23 C27 0.3(6) . . . . ? C21 C22 C23 C24 -179.4(4) . . . . ? C27 C23 C24 C25 -1.0(5) . . . . ? C22 C23 C24 C25 178.8(4) . . . . ? C23 C24 C25 C26 0.8(6) . . . . ? C27 N5 C26 C25 -0.3(5) . . . . ? Zn1 N5 C26 C25 172.6(3) . . . . ? C24 C25 C26 N5 -0.1(6) . . . . ? C26 N5 C27 C23 0.1(5) . . . . ? Zn1 N5 C27 C23 -174.1(3) . . . . ? C26 N5 C27 C28 179.7(3) . . . . ? Zn1 N5 C27 C28 5.5(4) . . . . ? C24 C23 C27 N5 0.5(5) . . . . ? C22 C23 C27 N5 -179.2(3) . . . . ? C24 C23 C27 C28 -179.1(3) . . . . ? C22 C23 C27 C28 1.2(5) . . . . ? C17 N4 C28 C20 0.8(5) . . . . ? Zn1 N4 C28 C20 175.6(3) . . . . ? C17 N4 C28 C27 -179.1(3) . . . . ? Zn1 N4 C28 C27 -4.3(4) . . . . ? C19 C20 C28 N4 -1.0(5) . . . . ? C21 C20 C28 N4 180.0(3) . . . . ? C19 C20 C28 C27 178.9(3) . . . . ? C21 C20 C28 C27 -0.1(5) . . . . ? N5 C27 C28 N4 -0.9(5) . . . . ? C23 C27 C28 N4 178.7(3) . . . . ? N5 C27 C28 C20 179.1(3) . . . . ? C23 C27 C28 C20 -1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.480 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.079 # Attachment 'complex 1.cif' data_r71017e _database_code_depnum_ccdc_archive 'CCDC 668447' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 N6 O10 Zn' _chemical_formula_weight 660.92 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.328(2) _cell_length_b 26.647(5) _cell_length_c 10.672(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.89(3) _cell_angle_gamma 90.00 _cell_volume 2795.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4828 _cell_measurement_theta_min 2.519 _cell_measurement_theta_max 25.011 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1364 _exptl_absorpt_coefficient_mu 0.949 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9630 _exptl_absorpt_correction_T_max 0.9813 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17112 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4935 _reflns_number_gt 4093 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0753P)^2^+5.5354P] 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 4935 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.1821 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 Zn1 Zn 0.47451(6) 0.11825(2) 0.15175(5) 0.0299(2) Uani 1 1 d . . . O1 O 0.6449(3) 0.12200(14) 0.0828(4) 0.0359(9) Uani 1 1 d . . . O2 O 0.7346(5) 0.08735(17) -0.0647(5) 0.0583(12) Uani 1 1 d . . . N1 N 0.4720(4) 0.04467(16) 0.0516(4) 0.0283(9) Uani 1 1 d . . . N2 N 0.3498(4) 0.15772(16) -0.0153(4) 0.0302(10) Uani 1 1 d . . . N3 N 0.5080(4) 0.19482(16) 0.2177(4) 0.0297(9) Uani 1 1 d . . . N4 N 0.3110(4) 0.09628(17) 0.2248(4) 0.0323(10) Uani 1 1 d . . . N5 N 0.5815(5) 0.08975(17) 0.3411(4) 0.0364(11) Uani 1 1 d . . . C1 C 0.6607(6) 0.0875(2) 0.0066(5) 0.0362(13) Uani 1 1 d . . . C2 C 0.5759(5) 0.0407(2) 0.0030(5) 0.0306(12) Uani 1 1 d . . . C3 C 0.6036(5) -0.0041(2) -0.0482(5) 0.0322(12) Uani 1 1 d . . . H3 H 0.6770 -0.0059 -0.0813 0.039 Uiso 1 1 calc R . . C4 C 0.2718(5) 0.1389(2) -0.1298(5) 0.0334(12) Uani 1 1 d . . . H4 H 0.2682 0.1043 -0.1413 0.040 Uiso 1 1 calc R . . C5 C 0.1956(5) 0.1693(2) -0.2324(5) 0.0381(13) Uani 1 1 d . . . H5 H 0.1430 0.1551 -0.3112 0.046 Uiso 1 1 calc R . . C6 C 0.1991(5) 0.2201(2) -0.2161(5) 0.0359(13) Uani 1 1 d . . . H6 H 0.1479 0.2407 -0.2835 0.043 Uiso 1 1 calc R . . C7 C 0.2800(5) 0.2412(2) -0.0977(5) 0.0320(12) Uani 1 1 d . . . C8 C 0.2917(6) 0.2939(2) -0.0731(6) 0.0391(14) Uani 1 1 d . . . H8 H 0.2405 0.3160 -0.1366 0.047 Uiso 1 1 calc R . . C9 C 0.3749(6) 0.3120(2) 0.0397(6) 0.0380(13) Uani 1 1 d . . . H9 H 0.3818 0.3466 0.0522 0.046 Uiso 1 1 calc R . . C10 C 0.4530(5) 0.2800(2) 0.1408(5) 0.0319(12) Uani 1 1 d . . . C11 C 0.5419(5) 0.2977(2) 0.2608(5) 0.0366(13) Uani 1 1 d . . . H11 H 0.5547 0.3320 0.2757 0.044 Uiso 1 1 calc R . . C12 C 0.6094(5) 0.2640(2) 0.3554(5) 0.0377(13) Uani 1 1 d . . . H12 H 0.6683 0.2751 0.4352 0.045 Uiso 1 1 calc R . . C13 C 0.5885(5) 0.2128(2) 0.3300(5) 0.0333(12) Uani 1 1 d . . . H13 H 0.6333 0.1902 0.3954 0.040 Uiso 1 1 calc R . . C14 C 0.4412(5) 0.22815(19) 0.1233(5) 0.0256(11) Uani 1 1 d . . . C15 C 0.3547(5) 0.2081(2) 0.0010(5) 0.0274(11) Uani 1 1 d . . . C16 C 0.1765(6) 0.0972(2) 0.1653(5) 0.0405(13) Uani 1 1 d . . . H16 H 0.1449 0.1086 0.0787 0.049 Uiso 1 1 calc R . . C17 C 0.0815(7) 0.0822(3) 0.2258(7) 0.0543(17) Uani 1 1 d . . . H17 H -0.0110 0.0823 0.1801 0.065 Uiso 1 1 calc R . . C18 C 0.1277(7) 0.0673(3) 0.3544(7) 0.0561(17) Uani 1 1 d . . . H18 H 0.0659 0.0582 0.3980 0.067 Uiso 1 1 calc R . . C19 C 0.2671(6) 0.0657(2) 0.4207(5) 0.0423(14) Uani 1 1 d . . . C20 C 0.3224(9) 0.0506(2) 0.5565(6) 0.059(2) Uani 1 1 d . . . H20 H 0.2640 0.0411 0.6035 0.071 Uiso 1 1 calc R . . C21 C 0.4578(9) 0.0501(3) 0.6159(6) 0.063(2) Uani 1 1 d . . . H21 H 0.4913 0.0408 0.7040 0.076 Uiso 1 1 calc R . . C22 C 0.5509(7) 0.0634(2) 0.5468(5) 0.0465(16) Uani 1 1 d . . . C23 C 0.6931(8) 0.0621(2) 0.6028(6) 0.060(2) Uani 1 1 d . . . H23 H 0.7315 0.0532 0.6907 0.072 Uiso 1 1 calc R . . C24 C 0.7736(7) 0.0737(3) 0.5289(7) 0.061(2) Uani 1 1 d . . . H24 H 0.8677 0.0728 0.5653 0.074 Uiso 1 1 calc R . . C25 C 0.7141(6) 0.0874(2) 0.3966(6) 0.0476(16) Uani 1 1 d . . . H25 H 0.7707 0.0950 0.3462 0.057 Uiso 1 1 calc R . . C26 C 0.4994(6) 0.0778(2) 0.4141(5) 0.0383(13) Uani 1 1 d . . . C27 C 0.3548(6) 0.0800(2) 0.3516(5) 0.0339(12) Uani 1 1 d . . . N6 N 0.8858(6) 0.9753(3) 0.2092(8) 0.082(2) Uani 1 1 d . . . O3 O 0.8172(5) 1.01117(19) 0.2270(5) 0.0643(13) Uani 1 1 d . . . O4 O 0.9298(6) 0.9446(3) 0.2982(8) 0.129(3) Uani 1 1 d . . . O5 O 0.9063(8) 0.9697(3) 0.0929(8) 0.133(3) Uani 1 1 d . . . O6 O 0.0252(4) 0.20335(15) 1.0349(3) 0.0397(9) Uani 1 1 d . . . H6A H 0.0261 0.1829 0.9740 0.048 Uiso 1 1 d R . . H6B H 0.0032 0.2335 1.0113 0.048 Uiso 1 1 d R . . O7 O 0.8440(4) 0.19746(14) 0.1797(3) 0.0381(9) Uani 1 1 d . . . H7A H 0.7707 0.1803 0.1521 0.046 Uiso 1 1 d R . . H7B H 0.8974 0.1955 0.1324 0.046 Uiso 1 1 d R . . O8 O 0.8100(4) 0.19549(16) 0.6238(3) 0.0435(10) Uani 1 1 d . . . H8A H 0.8110 0.2270 0.6387 0.052 Uiso 1 1 d R . . H8B H 0.8520 0.1775 0.6902 0.052 Uiso 1 1 d R . . O9 O 0.9699(3) 0.30344(11) 0.9542(3) 0.0470(11) Uani 1 1 d . . . H9A H 0.9337 0.3111 0.8737 0.056 Uiso 1 1 d R . . H9B H 0.9262 0.3117 1.0069 0.11(3) Uiso 1 1 d R . . O10 O 0.9249(3) 0.13031(11) 0.8434(3) 0.0421(10) Uani 1 1 d R . . H10A H 0.8522 0.1486 0.8382 0.051 Uiso 1 1 d R . . H10B H 0.9036 0.0984 0.8352 0.051 Uiso 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 Zn1 0.0334(3) 0.0220(4) 0.0282(3) 0.0015(2) 0.0005(2) -0.0011(3) O1 0.0337(19) 0.026(2) 0.044(2) 0.0001(17) 0.0056(16) -0.0050(16) O2 0.067(3) 0.045(3) 0.078(3) -0.006(2) 0.044(3) -0.018(2) N1 0.032(2) 0.023(2) 0.028(2) 0.0039(18) 0.0067(18) 0.0005(18) N2 0.029(2) 0.026(3) 0.031(2) 0.0040(19) 0.0031(18) -0.0016(19) N3 0.030(2) 0.023(2) 0.032(2) 0.0016(19) 0.0031(18) -0.0014(18) N4 0.038(2) 0.027(3) 0.028(2) -0.0040(19) 0.0047(19) -0.001(2) N5 0.043(3) 0.020(2) 0.034(2) -0.0025(19) -0.006(2) 0.002(2) C1 0.040(3) 0.021(3) 0.044(3) 0.004(2) 0.009(3) -0.003(2) C2 0.034(3) 0.029(3) 0.027(2) 0.005(2) 0.006(2) -0.004(2) C3 0.037(3) 0.027(3) 0.033(3) 0.001(2) 0.011(2) -0.004(2) C4 0.033(3) 0.034(3) 0.028(3) 0.002(2) 0.001(2) -0.008(2) C5 0.031(3) 0.052(4) 0.026(3) 0.005(3) 0.002(2) 0.001(3) C6 0.026(3) 0.050(4) 0.031(3) 0.016(3) 0.008(2) 0.008(2) C7 0.033(3) 0.032(3) 0.031(3) 0.012(2) 0.010(2) 0.004(2) C8 0.042(3) 0.032(3) 0.045(3) 0.019(3) 0.016(3) 0.015(3) C9 0.049(3) 0.020(3) 0.052(3) 0.007(3) 0.026(3) 0.003(2) C10 0.037(3) 0.024(3) 0.039(3) 0.005(2) 0.019(2) 0.004(2) C11 0.043(3) 0.025(3) 0.048(3) -0.007(3) 0.023(3) -0.004(2) C12 0.040(3) 0.034(3) 0.038(3) -0.008(3) 0.011(2) -0.006(3) C13 0.032(3) 0.033(3) 0.029(3) -0.001(2) 0.000(2) -0.004(2) C14 0.023(2) 0.026(3) 0.031(2) 0.002(2) 0.013(2) 0.002(2) C15 0.024(2) 0.028(3) 0.030(3) 0.005(2) 0.009(2) 0.000(2) C16 0.045(3) 0.037(4) 0.034(3) 0.002(3) 0.005(2) -0.001(3) C17 0.045(3) 0.056(5) 0.066(4) -0.003(4) 0.024(3) -0.008(3) C18 0.076(5) 0.046(4) 0.058(4) 0.000(3) 0.037(4) -0.004(4) C19 0.064(4) 0.026(3) 0.038(3) -0.004(3) 0.018(3) -0.005(3) C20 0.117(6) 0.027(4) 0.039(3) -0.001(3) 0.033(4) -0.008(4) C21 0.116(7) 0.031(4) 0.032(3) 0.001(3) 0.006(4) -0.003(4) C22 0.075(4) 0.021(3) 0.028(3) 0.001(2) -0.007(3) 0.001(3) C23 0.087(5) 0.029(4) 0.038(3) -0.005(3) -0.022(4) 0.003(4) C24 0.057(4) 0.037(4) 0.058(4) -0.012(3) -0.030(3) 0.014(3) C25 0.045(3) 0.027(3) 0.054(4) -0.001(3) -0.011(3) 0.006(3) C26 0.055(3) 0.017(3) 0.032(3) -0.003(2) -0.002(3) 0.001(3) C27 0.050(3) 0.017(3) 0.030(3) -0.002(2) 0.006(2) -0.002(2) N6 0.048(4) 0.058(5) 0.120(6) -0.003(5) -0.004(4) -0.006(3) O3 0.060(3) 0.052(3) 0.080(3) -0.002(3) 0.021(3) 0.017(3) O4 0.083(4) 0.080(5) 0.165(7) 0.042(5) -0.049(4) 0.002(4) O5 0.157(7) 0.136(7) 0.121(6) -0.077(6) 0.065(5) -0.032(6) O6 0.045(2) 0.037(2) 0.036(2) -0.0056(17) 0.0099(17) -0.0026(18) O7 0.045(2) 0.038(2) 0.0324(19) -0.0054(17) 0.0130(16) -0.0155(18) O8 0.055(2) 0.042(3) 0.0311(19) 0.0028(18) 0.0094(18) -0.002(2) O9 0.043(2) 0.063(3) 0.031(2) 0.0029(19) 0.0066(18) -0.002(2) O10 0.046(2) 0.039(2) 0.039(2) -0.0028(18) 0.0081(17) -0.0122(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 Zn1 O1 2.108(4) . ? Zn1 N5 2.123(4) . ? Zn1 N2 2.129(4) . ? Zn1 N4 2.148(4) . ? Zn1 N3 2.152(4) . ? Zn1 N1 2.230(4) . ? O1 C1 1.270(7) . ? O2 C1 1.233(7) . ? N1 C3 1.327(6) 3_655 ? N1 C2 1.332(6) . ? N2 C4 1.338(6) . ? N2 C15 1.354(7) . ? N3 C13 1.321(6) . ? N3 C14 1.361(6) . ? N4 C16 1.339(7) . ? N4 C27 1.359(6) . ? N5 C25 1.317(7) . ? N5 C26 1.354(8) . ? C1 C2 1.518(7) . ? C2 C3 1.379(7) . ? C3 N1 1.327(6) 3_655 ? C3 H3 0.9300 . ? C4 C5 1.395(7) . ? C4 H4 0.9300 . ? C5 C6 1.364(8) . ? C5 H5 0.9300 . ? C6 C7 1.401(7) . ? C6 H6 0.9300 . ? C7 C15 1.407(7) . ? C7 C8 1.426(8) . ? C8 C9 1.337(8) . ? C8 H8 0.9300 . ? C9 C10 1.417(7) . ? C9 H9 0.9300 . ? C10 C14 1.395(7) . ? C10 C11 1.408(7) . ? C11 C12 1.372(8) . ? C11 H11 0.9300 . ? C12 C13 1.394(8) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.439(7) . ? C16 C17 1.389(8) . ? C16 H16 0.9300 . ? C17 C18 1.366(9) . ? C17 H17 0.9300 . ? C18 C19 1.396(9) . ? C18 H18 0.9300 . ? C19 C27 1.386(8) . ? C19 C20 1.442(9) . ? C20 C21 1.347(10) . ? C20 H20 0.9300 . ? C21 C22 1.424(10) . ? C21 H21 0.9300 . ? C22 C26 1.406(7) . ? C22 C23 1.406(9) . ? C23 C24 1.345(10) . ? C23 H23 0.9300 . ? C24 C25 1.404(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.437(8) . ? N6 O4 1.231(9) . ? N6 O3 1.238(8) . ? N6 O5 1.329(10) . ? O6 H6A 0.8501 . ? O6 H6B 0.8516 . ? O7 H7A 0.8547 . ? O7 H7B 0.8560 . ? O8 H8A 0.8544 . ? O8 H8B 0.8556 . ? O9 H9A 0.8496 . ? O9 H9B 0.8516 . ? O10 H10A 0.8829 . ? O10 H10B 0.8771 . ? 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 Zn1 N5 95.90(17) . . ? O1 Zn1 N2 92.26(15) . . ? N5 Zn1 N2 167.86(17) . . ? O1 Zn1 N4 166.80(16) . . ? N5 Zn1 N4 78.13(17) . . ? N2 Zn1 N4 95.62(16) . . ? O1 Zn1 N3 90.09(15) . . ? N5 Zn1 N3 92.49(16) . . ? N2 Zn1 N3 78.50(16) . . ? N4 Zn1 N3 101.84(16) . . ? O1 Zn1 N1 76.26(15) . . ? N5 Zn1 N1 93.89(16) . . ? N2 Zn1 N1 96.77(16) . . ? N4 Zn1 N1 92.27(16) . . ? N3 Zn1 N1 165.45(16) . . ? C1 O1 Zn1 118.3(3) . . ? C3 N1 C2 117.5(5) 3_655 . ? C3 N1 Zn1 130.5(3) 3_655 . ? C2 N1 Zn1 111.4(3) . . ? C4 N2 C15 118.5(4) . . ? C4 N2 Zn1 128.2(4) . . ? C15 N2 Zn1 113.2(3) . . ? C13 N3 C14 118.0(5) . . ? C13 N3 Zn1 129.4(4) . . ? C14 N3 Zn1 112.5(3) . . ? C16 N4 C27 117.3(5) . . ? C16 N4 Zn1 129.7(4) . . ? C27 N4 Zn1 112.9(3) . . ? C25 N5 C26 118.6(5) . . ? C25 N5 Zn1 127.6(4) . . ? C26 N5 Zn1 113.4(3) . . ? O2 C1 O1 128.6(5) . . ? O2 C1 C2 116.3(5) . . ? O1 C1 C2 115.1(5) . . ? N1 C2 C3 120.9(5) . . ? N1 C2 C1 116.9(5) . . ? C3 C2 C1 122.2(5) . . ? N1 C3 C2 121.6(5) 3_655 . ? N1 C3 H3 119.2 3_655 . ? C2 C3 H3 119.2 . . ? N2 C4 C5 122.4(5) . . ? N2 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C6 C5 C4 119.3(5) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 119.9(5) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C15 117.5(5) . . ? C6 C7 C8 123.6(5) . . ? C15 C7 C8 118.9(5) . . ? C9 C8 C7 121.0(5) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 121.8(5) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C14 C10 C11 117.4(5) . . ? C14 C10 C9 119.2(5) . . ? C11 C10 C9 123.4(5) . . ? C12 C11 C10 119.4(5) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.0(5) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? N3 C13 C12 123.3(5) . . ? N3 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? N3 C14 C10 122.9(5) . . ? N3 C14 C15 117.5(5) . . ? C10 C14 C15 119.5(5) . . ? N2 C15 C7 122.4(5) . . ? N2 C15 C14 118.2(4) . . ? C7 C15 C14 119.4(5) . . ? N4 C16 C17 123.5(5) . . ? N4 C16 H16 118.3 . . ? C17 C16 H16 118.3 . . ? C18 C17 C16 118.2(6) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? C17 C18 C19 120.3(6) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C27 C19 C18 117.6(5) . . ? C27 C19 C20 119.3(6) . . ? C18 C19 C20 123.1(6) . . ? C21 C20 C19 120.7(7) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 121.5(6) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C26 C22 C23 117.2(6) . . ? C26 C22 C21 118.9(6) . . ? C23 C22 C21 123.9(6) . . ? C24 C23 C22 119.9(6) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 119.4(6) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? N5 C25 C24 122.5(7) . . ? N5 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? N5 C26 C22 122.3(5) . . ? N5 C26 C27 118.0(5) . . ? C22 C26 C27 119.7(6) . . ? N4 C27 C19 123.0(5) . . ? N4 C27 C26 117.1(5) . . ? C19 C27 C26 119.9(5) . . ? O4 N6 O3 119.2(9) . . ? O4 N6 O5 121.1(9) . . ? O3 N6 O5 119.6(8) . . ? H6A O6 H6B 116.4 . . ? H7A O7 H7B 115.2 . . ? H8A O8 H8B 115.0 . . ? H9A O9 H9B 116.6 . . ? H10A O10 H10B 110.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Zn1 O1 C1 101.2(4) . . . . ? N2 Zn1 O1 C1 -87.8(4) . . . . ? N4 Zn1 O1 C1 38.9(8) . . . . ? N3 Zn1 O1 C1 -166.3(4) . . . . ? N1 Zn1 O1 C1 8.6(4) . . . . ? O1 Zn1 N1 C3 171.4(4) . . . 3_655 ? N5 Zn1 N1 C3 76.3(4) . . . 3_655 ? N2 Zn1 N1 C3 -97.9(4) . . . 3_655 ? N4 Zn1 N1 C3 -2.0(4) . . . 3_655 ? N3 Zn1 N1 C3 -167.9(5) . . . 3_655 ? O1 Zn1 N1 C2 0.8(3) . . . . ? N5 Zn1 N1 C2 -94.4(3) . . . . ? N2 Zn1 N1 C2 91.4(3) . . . . ? N4 Zn1 N1 C2 -172.6(3) . . . . ? N3 Zn1 N1 C2 21.4(8) . . . . ? O1 Zn1 N2 C4 90.6(4) . . . . ? N5 Zn1 N2 C4 -137.1(8) . . . . ? N4 Zn1 N2 C4 -78.8(4) . . . . ? N3 Zn1 N2 C4 -179.8(5) . . . . ? N1 Zn1 N2 C4 14.2(4) . . . . ? O1 Zn1 N2 C15 -88.8(3) . . . . ? N5 Zn1 N2 C15 43.5(10) . . . . ? N4 Zn1 N2 C15 101.8(3) . . . . ? N3 Zn1 N2 C15 0.9(3) . . . . ? N1 Zn1 N2 C15 -165.2(3) . . . . ? O1 Zn1 N3 C13 -85.4(4) . . . . ? N5 Zn1 N3 C13 10.5(5) . . . . ? N2 Zn1 N3 C13 -177.7(5) . . . . ? N4 Zn1 N3 C13 88.9(4) . . . . ? N1 Zn1 N3 C13 -105.5(7) . . . . ? O1 Zn1 N3 C14 89.9(3) . . . . ? N5 Zn1 N3 C14 -174.2(3) . . . . ? N2 Zn1 N3 C14 -2.4(3) . . . . ? N4 Zn1 N3 C14 -95.8(3) . . . . ? N1 Zn1 N3 C14 69.9(7) . . . . ? O1 Zn1 N4 C16 -112.3(7) . . . . ? N5 Zn1 N4 C16 -176.5(5) . . . . ? N2 Zn1 N4 C16 14.1(5) . . . . ? N3 Zn1 N4 C16 93.5(5) . . . . ? N1 Zn1 N4 C16 -83.0(5) . . . . ? O1 Zn1 N4 C27 68.9(7) . . . . ? N5 Zn1 N4 C27 4.8(4) . . . . ? N2 Zn1 N4 C27 -164.7(4) . . . . ? N3 Zn1 N4 C27 -85.3(4) . . . . ? N1 Zn1 N4 C27 98.3(4) . . . . ? O1 Zn1 N5 C25 12.6(5) . . . . ? N2 Zn1 N5 C25 -119.4(8) . . . . ? N4 Zn1 N5 C25 -179.3(5) . . . . ? N3 Zn1 N5 C25 -77.7(5) . . . . ? N1 Zn1 N5 C25 89.2(5) . . . . ? O1 Zn1 N5 C26 -174.4(4) . . . . ? N2 Zn1 N5 C26 53.5(10) . . . . ? N4 Zn1 N5 C26 -6.4(4) . . . . ? N3 Zn1 N5 C26 95.2(4) . . . . ? N1 Zn1 N5 C26 -97.9(4) . . . . ? Zn1 O1 C1 O2 164.0(5) . . . . ? Zn1 O1 C1 C2 -15.5(6) . . . . ? C3 N1 C2 C3 -0.2(8) 3_655 . . . ? Zn1 N1 C2 C3 171.8(4) . . . . ? C3 N1 C2 C1 179.5(4) 3_655 . . . ? Zn1 N1 C2 C1 -8.5(5) . . . . ? O2 C1 C2 N1 -163.4(5) . . . . ? O1 C1 C2 N1 16.2(7) . . . . ? O2 C1 C2 C3 16.3(8) . . . . ? O1 C1 C2 C3 -164.1(5) . . . . ? N1 C2 C3 N1 0.2(8) . . . 3_655 ? C1 C2 C3 N1 -179.5(4) . . . 3_655 ? C15 N2 C4 C5 0.0(7) . . . . ? Zn1 N2 C4 C5 -179.3(4) . . . . ? N2 C4 C5 C6 -0.6(8) . . . . ? C4 C5 C6 C7 0.8(8) . . . . ? C5 C6 C7 C15 -0.4(7) . . . . ? C5 C6 C7 C8 178.8(5) . . . . ? C6 C7 C8 C9 -177.1(5) . . . . ? C15 C7 C8 C9 2.0(8) . . . . ? C7 C8 C9 C10 -1.3(8) . . . . ? C8 C9 C10 C14 -1.1(8) . . . . ? C8 C9 C10 C11 179.9(5) . . . . ? C14 C10 C11 C12 -1.6(7) . . . . ? C9 C10 C11 C12 177.3(5) . . . . ? C10 C11 C12 C13 0.2(8) . . . . ? C14 N3 C13 C12 -1.0(7) . . . . ? Zn1 N3 C13 C12 174.2(4) . . . . ? C11 C12 C13 N3 1.2(8) . . . . ? C13 N3 C14 C10 -0.6(7) . . . . ? Zn1 N3 C14 C10 -176.6(4) . . . . ? C13 N3 C14 C15 179.5(4) . . . . ? Zn1 N3 C14 C15 3.5(5) . . . . ? C11 C10 C14 N3 1.9(7) . . . . ? C9 C10 C14 N3 -177.1(4) . . . . ? C11 C10 C14 C15 -178.2(4) . . . . ? C9 C10 C14 C15 2.8(7) . . . . ? C4 N2 C15 C7 0.5(7) . . . . ? Zn1 N2 C15 C7 179.9(4) . . . . ? C4 N2 C15 C14 -178.7(4) . . . . ? Zn1 N2 C15 C14 0.7(5) . . . . ? C6 C7 C15 N2 -0.3(7) . . . . ? C8 C7 C15 N2 -179.5(5) . . . . ? C6 C7 C15 C14 178.9(4) . . . . ? C8 C7 C15 C14 -0.4(7) . . . . ? N3 C14 C15 N2 -3.0(6) . . . . ? C10 C14 C15 N2 177.2(4) . . . . ? N3 C14 C15 C7 177.9(4) . . . . ? C10 C14 C15 C7 -2.0(7) . . . . ? C27 N4 C16 C17 -0.6(9) . . . . ? Zn1 N4 C16 C17 -179.3(5) . . . . ? N4 C16 C17 C18 2.3(10) . . . . ? C16 C17 C18 C19 -2.2(10) . . . . ? C17 C18 C19 C27 0.5(10) . . . . ? C17 C18 C19 C20 179.6(6) . . . . ? C27 C19 C20 C21 -0.4(9) . . . . ? C18 C19 C20 C21 -179.5(6) . . . . ? C19 C20 C21 C22 -1.2(10) . . . . ? C20 C21 C22 C26 0.6(9) . . . . ? C20 C21 C22 C23 -178.0(6) . . . . ? C26 C22 C23 C24 -0.9(9) . . . . ? C21 C22 C23 C24 177.8(6) . . . . ? C22 C23 C24 C25 0.3(10) . . . . ? C26 N5 C25 C24 -1.1(8) . . . . ? Zn1 N5 C25 C24 171.5(4) . . . . ? C23 C24 C25 N5 0.7(10) . . . . ? C25 N5 C26 C22 0.4(8) . . . . ? Zn1 N5 C26 C22 -173.2(4) . . . . ? C25 N5 C26 C27 -179.2(5) . . . . ? Zn1 N5 C26 C27 7.2(6) . . . . ? C23 C22 C26 N5 0.5(8) . . . . ? C21 C22 C26 N5 -178.3(5) . . . . ? C23 C22 C26 C27 -179.8(5) . . . . ? C21 C22 C26 C27 1.4(8) . . . . ? C16 N4 C27 C19 -1.4(8) . . . . ? Zn1 N4 C27 C19 177.6(4) . . . . ? C16 N4 C27 C26 178.5(5) . . . . ? Zn1 N4 C27 C26 -2.6(6) . . . . ? C18 C19 C27 N4 1.4(9) . . . . ? C20 C19 C27 N4 -177.8(5) . . . . ? C18 C19 C27 C26 -178.4(5) . . . . ? C20 C19 C27 C26 2.4(8) . . . . ? N5 C26 C27 N4 -3.1(7) . . . . ? C22 C26 C27 N4 177.3(5) . . . . ? N5 C26 C27 C19 176.7(5) . . . . ? C22 C26 C27 C19 -2.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.814 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.092 # Attachment 'complex 4.cif' data_71015b _database_code_depnum_ccdc_archive 'CCDC 668448' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 Cu N6 O10' _chemical_formula_weight 659.09 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 10.3969(19) _cell_length_b 26.575(5) _cell_length_c 10.705(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.183(3) _cell_angle_gamma 90.00 _cell_volume 2810.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2961 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 24.67 _exptl_crystal_description prisme _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.847 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8489 _exptl_absorpt_correction_T_max 0.9201 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15941 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.40 _reflns_number_total 5724 _reflns_number_gt 3384 _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^)+(0.0673P)^2^+0.9042P] 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 5724 _refine_ls_number_parameters 397 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.003 _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 0.97464(5) 0.117626(16) 0.15041(4) 0.03188(17) Uani 1 1 d . . . O1 O 1.1536(3) 0.12184(10) 0.0743(3) 0.0496(8) Uani 1 1 d . . . O2 O 1.2204(4) 0.08711(13) -0.0838(4) 0.0679(10) Uani 1 1 d . . . N1 N 0.9769(3) 0.04507(12) 0.0543(3) 0.0337(8) Uani 1 1 d . . . N2 N 0.8609(3) 0.15367(12) -0.0111(3) 0.0359(8) Uani 1 1 d . . . N3 N 1.0148(3) 0.19270(12) 0.2167(3) 0.0359(8) Uani 1 1 d . . . N4 N 0.8067(3) 0.09463(12) 0.2215(3) 0.0377(8) Uani 1 1 d . . . N5 N 1.0769(3) 0.09008(12) 0.3266(3) 0.0350(8) Uani 1 1 d . . . C1 C 1.1584(4) 0.08728(16) -0.0031(4) 0.0402(11) Uani 1 1 d . . . C2 C 1.0744(4) 0.04111(14) -0.0023(3) 0.0292(9) Uani 1 1 d . . . C3 C 0.9033(4) 0.00439(14) 0.0553(4) 0.0339(10) Uani 1 1 d . . . H3 H 0.8341 0.0065 0.0930 0.041 Uiso 1 1 calc R . . C4 C 0.7848(4) 0.13406(17) -0.1228(4) 0.0463(12) Uani 1 1 d . . . H4 H 0.7824 0.0992 -0.1318 0.056 Uiso 1 1 calc R . . C5 C 0.7081(5) 0.1629(2) -0.2277(4) 0.0561(14) Uani 1 1 d . . . H5 H 0.6568 0.1475 -0.3052 0.067 Uiso 1 1 calc R . . C6 C 0.7086(5) 0.21407(19) -0.2163(5) 0.0519(13) Uani 1 1 d . . . H6 H 0.6560 0.2338 -0.2852 0.062 Uiso 1 1 calc R . . C7 C 0.7889(4) 0.23663(16) -0.1001(4) 0.0420(11) Uani 1 1 d . . . C8 C 0.7990(5) 0.28945(18) -0.0780(5) 0.0574(14) Uani 1 1 d . . . H8 H 0.7477 0.3110 -0.1429 0.069 Uiso 1 1 calc R . . C9 C 0.8807(5) 0.30875(17) 0.0342(5) 0.0585(14) Uani 1 1 d . . . H9 H 0.8861 0.3435 0.0445 0.070 Uiso 1 1 calc R . . C10 C 0.9594(5) 0.27775(16) 0.1378(5) 0.0448(11) Uani 1 1 d . . . C11 C 1.0473(5) 0.29583(19) 0.2567(5) 0.0575(14) Uani 1 1 d . . . H11 H 1.0599 0.3303 0.2706 0.069 Uiso 1 1 calc R . . C12 C 1.1146(5) 0.26270(19) 0.3523(5) 0.0556(13) Uani 1 1 d . . . H12 H 1.1730 0.2742 0.4318 0.067 Uiso 1 1 calc R . . C13 C 1.0943(4) 0.21163(18) 0.3287(4) 0.0472(12) Uani 1 1 d . . . H13 H 1.1390 0.1894 0.3952 0.057 Uiso 1 1 calc R . . C14 C 0.9479(4) 0.22564(15) 0.1223(4) 0.0343(10) Uani 1 1 d . . . C15 C 0.8633(4) 0.20460(15) 0.0018(4) 0.0332(9) Uani 1 1 d . . . C16 C 0.6736(5) 0.09478(17) 0.1664(5) 0.0499(12) Uani 1 1 d . . . H16 H 0.6382 0.1046 0.0789 0.060 Uiso 1 1 calc R . . C17 C 0.5844(5) 0.0809(2) 0.2341(6) 0.0658(15) Uani 1 1 d . . . H17 H 0.4915 0.0812 0.1919 0.079 Uiso 1 1 calc R . . C18 C 0.6343(6) 0.06691(19) 0.3620(6) 0.0668(15) Uani 1 1 d . . . H18 H 0.5754 0.0578 0.4081 0.080 Uiso 1 1 calc R . . C19 C 0.7739(5) 0.06614(15) 0.4246(5) 0.0455(11) Uani 1 1 d . . . C20 C 0.8357(7) 0.05242(18) 0.5586(5) 0.0626(15) Uani 1 1 d . . . H20 H 0.7815 0.0435 0.6097 0.075 Uiso 1 1 calc R . . C21 C 0.9704(7) 0.05208(17) 0.6122(5) 0.0609(16) Uani 1 1 d . . . H21 H 1.0077 0.0432 0.7002 0.073 Uiso 1 1 calc R . . C22 C 1.0593(5) 0.06509(15) 0.5376(4) 0.0464(12) Uani 1 1 d . . . C23 C 1.2011(6) 0.06356(17) 0.5857(5) 0.0618(16) Uani 1 1 d . . . H23 H 1.2439 0.0550 0.6730 0.074 Uiso 1 1 calc R . . C24 C 1.2761(5) 0.07446(17) 0.5065(5) 0.0569(14) Uani 1 1 d . . . H24 H 1.3702 0.0732 0.5381 0.068 Uiso 1 1 calc R . . C25 C 1.2096(5) 0.08765(16) 0.3766(4) 0.0475(12) Uani 1 1 d . . . H25 H 1.2615 0.0951 0.3223 0.057 Uiso 1 1 calc R . . C26 C 1.0008(5) 0.07810(13) 0.4053(4) 0.0356(10) Uani 1 1 d . . . C27 C 0.8565(4) 0.07973(14) 0.3488(4) 0.0358(10) Uani 1 1 d . . . N6 N 0.6120(5) 0.0254(2) 0.7769(6) 0.0727(15) Uani 1 1 d . . . O3 O 0.5644(5) 0.0524(3) 0.6911(7) 0.169(3) Uani 1 1 d . . . O4 O 0.6894(5) -0.00582(19) 0.7757(5) 0.1096(17) Uani 1 1 d . . . O5 O 0.5812(7) 0.0332(3) 0.8832(8) 0.171(3) Uani 1 1 d . . . O6 O 0.4226(3) 0.13116(12) 0.8461(3) 0.0594(9) Uani 1 1 d D . . H6A H 0.3561 0.1256 0.8749 0.071 Uiso 1 1 d RD . . H6B H 0.4666 0.1053 0.8352 0.071 Uiso 1 1 d RD . . O7 O 0.4783(4) 0.30621(15) 0.9573(4) 0.0786(11) Uani 1 1 d D . . H7A H 0.4426 0.3070 0.8745 0.094 Uiso 1 1 d RD . . H7B H 0.4251 0.3043 1.0033 0.094 Uiso 1 1 d RD . . O8 O 0.3177(4) 0.19689(14) 0.6269(3) 0.0731(11) Uani 1 1 d D . . H8A H 0.3241 0.2268 0.6568 0.088 Uiso 1 1 d RD . . H8B H 0.3621 0.1745 0.6802 0.088 Uiso 1 1 d RD . . O9 O 0.3521(4) 0.19570(12) 0.1799(3) 0.0645(10) Uani 1 1 d D . . H9A H 0.2846 0.1760 0.1518 0.077 Uiso 1 1 d RD . . H9B H 0.4130 0.1932 0.1425 0.077 Uiso 1 1 d RD . . O10 O 0.5363(3) 0.20422(13) 0.0368(3) 0.0678(10) Uani 1 1 d D . . H10A H 0.5154 0.2335 0.0047 0.081 Uiso 1 1 d RD . . H10B H 0.4924 0.1797 -0.0076 0.081 Uiso 1 1 d RD . . 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 0.0351(3) 0.0282(3) 0.0266(3) 0.0016(2) 0.00139(19) -0.0007(2) O1 0.064(2) 0.0355(17) 0.0498(19) -0.0050(15) 0.0180(16) -0.0054(15) O2 0.085(3) 0.059(2) 0.079(3) -0.0128(19) 0.053(2) -0.024(2) N1 0.038(2) 0.0337(19) 0.0289(19) 0.0047(15) 0.0094(15) 0.0048(16) N2 0.035(2) 0.038(2) 0.0301(19) 0.0075(15) 0.0038(15) -0.0036(16) N3 0.0308(19) 0.041(2) 0.0318(19) 0.0032(16) 0.0041(15) 0.0003(16) N4 0.040(2) 0.0369(19) 0.033(2) -0.0028(16) 0.0080(16) 0.0051(16) N5 0.037(2) 0.0318(19) 0.0312(19) -0.0012(15) 0.0032(16) 0.0035(15) C1 0.044(3) 0.039(3) 0.039(3) 0.004(2) 0.013(2) -0.001(2) C2 0.029(2) 0.037(2) 0.022(2) 0.0071(17) 0.0087(17) 0.0024(18) C3 0.033(2) 0.037(2) 0.034(2) 0.0048(18) 0.0141(18) 0.0045(19) C4 0.043(3) 0.049(3) 0.036(3) 0.002(2) -0.003(2) -0.009(2) C5 0.046(3) 0.078(4) 0.032(3) 0.009(2) -0.004(2) -0.008(3) C6 0.040(3) 0.065(3) 0.044(3) 0.022(2) 0.003(2) 0.008(2) C7 0.031(2) 0.048(3) 0.048(3) 0.016(2) 0.014(2) 0.008(2) C8 0.064(3) 0.044(3) 0.069(4) 0.025(3) 0.027(3) 0.016(3) C9 0.074(4) 0.033(3) 0.076(4) 0.007(3) 0.035(3) 0.008(3) C10 0.046(3) 0.039(2) 0.057(3) 0.005(2) 0.027(2) -0.001(2) C11 0.061(3) 0.045(3) 0.076(4) -0.018(3) 0.035(3) -0.010(3) C12 0.051(3) 0.066(3) 0.049(3) -0.024(3) 0.015(2) -0.010(3) C13 0.041(3) 0.053(3) 0.043(3) -0.003(2) 0.006(2) -0.002(2) C14 0.031(2) 0.034(2) 0.041(3) 0.0042(18) 0.0167(19) 0.0011(18) C15 0.030(2) 0.036(2) 0.035(2) 0.0113(18) 0.0115(18) 0.0033(18) C16 0.044(3) 0.051(3) 0.052(3) -0.003(2) 0.009(2) 0.008(2) C17 0.044(3) 0.067(4) 0.091(5) 0.001(3) 0.029(3) -0.002(3) C18 0.074(4) 0.058(3) 0.089(4) -0.006(3) 0.055(4) -0.012(3) C19 0.065(3) 0.028(2) 0.052(3) -0.008(2) 0.031(3) -0.009(2) C20 0.103(5) 0.045(3) 0.053(3) 0.001(2) 0.043(3) -0.010(3) C21 0.116(5) 0.035(3) 0.031(3) 0.002(2) 0.023(3) -0.002(3) C22 0.072(4) 0.030(2) 0.028(2) -0.0013(18) 0.002(2) 0.004(2) C23 0.090(4) 0.039(3) 0.034(3) 0.000(2) -0.015(3) 0.008(3) C24 0.046(3) 0.050(3) 0.054(3) -0.005(2) -0.015(3) 0.011(2) C25 0.043(3) 0.044(3) 0.045(3) -0.002(2) -0.002(2) 0.005(2) C26 0.058(3) 0.0186(19) 0.027(2) -0.0053(16) 0.008(2) 0.0015(19) C27 0.053(3) 0.020(2) 0.034(2) -0.0029(17) 0.013(2) 0.0017(18) N6 0.045(3) 0.063(3) 0.095(4) -0.006(3) 0.000(3) -0.006(2) O3 0.089(4) 0.175(6) 0.191(6) 0.082(5) -0.031(4) 0.016(4) O4 0.102(4) 0.111(4) 0.121(4) 0.007(3) 0.042(3) 0.046(3) O5 0.202(7) 0.159(6) 0.186(7) -0.070(5) 0.109(6) -0.021(5) O6 0.058(2) 0.061(2) 0.063(2) -0.0054(17) 0.0238(18) -0.0144(17) O7 0.071(3) 0.111(3) 0.053(2) 0.001(2) 0.0183(19) 0.000(2) O8 0.088(3) 0.069(2) 0.060(2) 0.0078(19) 0.020(2) 0.007(2) O9 0.071(2) 0.064(2) 0.061(2) -0.0111(18) 0.0240(18) -0.0243(19) O10 0.076(3) 0.060(2) 0.063(2) -0.0095(18) 0.0151(19) -0.0104(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 1.993(3) . ? Cu1 N2 2.007(3) . ? Cu1 N3 2.115(3) . ? Cu1 N1 2.189(3) . ? Cu1 N4 2.198(4) . ? Cu1 O1 2.255(3) . ? O1 C1 1.248(5) . ? O2 C1 1.229(5) . ? N1 C3 1.327(5) . ? N1 C2 1.337(5) . ? N2 C4 1.318(5) . ? N2 C15 1.360(5) . ? N3 C13 1.325(5) . ? N3 C14 1.354(5) . ? N4 C16 1.324(5) . ? N4 C27 1.357(5) . ? N5 C25 1.317(5) . ? N5 C26 1.361(5) . ? C1 C2 1.507(6) . ? C2 C3 1.385(5) 3_755 ? C3 C2 1.385(5) 3_755 ? C3 H3 0.9300 . ? C4 C5 1.388(6) . ? C4 H4 0.9300 . ? C5 C6 1.365(7) . ? C5 H5 0.9300 . ? C6 C7 1.398(6) . ? C6 H6 0.9300 . ? C7 C15 1.410(5) . ? C7 C8 1.422(6) . ? C8 C9 1.338(7) . ? C8 H8 0.9300 . ? C9 C10 1.418(6) . ? C9 H9 0.9300 . ? C10 C14 1.396(6) . ? C10 C11 1.401(6) . ? C11 C12 1.365(7) . ? C11 H11 0.9300 . ? C12 C13 1.384(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.429(5) . ? C16 C17 1.393(7) . ? C16 H16 0.9300 . ? C17 C18 1.356(7) . ? C17 H17 0.9300 . ? C18 C19 1.397(7) . ? C18 H18 0.9300 . ? C19 C27 1.400(6) . ? C19 C20 1.425(7) . ? C20 C21 1.337(7) . ? C20 H20 0.9300 . ? C21 C22 1.440(7) . ? C21 H21 0.9300 . ? C22 C26 1.400(6) . ? C22 C23 1.402(7) . ? C23 C24 1.351(7) . ? C23 H23 0.9300 . ? C24 C25 1.391(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.432(6) . ? N6 O3 1.149(7) . ? N6 O4 1.158(6) . ? N6 O5 1.292(7) . ? O6 H6A 0.8531 . ? O6 H6B 0.8543 . ? O7 H7A 0.8480 . ? O7 H7B 0.8501 . ? O8 H8A 0.8509 . ? O8 H8B 0.8529 . ? O9 H9A 0.8514 . ? O9 H9B 0.8511 . ? O10 H10A 0.8507 . ? O10 H10B 0.8500 . ? 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 N5 Cu1 N2 170.86(14) . . ? N5 Cu1 N3 92.16(13) . . ? N2 Cu1 N3 80.82(13) . . ? N5 Cu1 N1 92.32(12) . . ? N2 Cu1 N1 96.05(12) . . ? N3 Cu1 N1 163.46(13) . . ? N5 Cu1 N4 79.44(14) . . ? N2 Cu1 N4 96.48(13) . . ? N3 Cu1 N4 103.93(13) . . ? N1 Cu1 N4 92.55(13) . . ? N5 Cu1 O1 95.95(13) . . ? N2 Cu1 O1 89.76(12) . . ? N3 Cu1 O1 88.61(12) . . ? N1 Cu1 O1 75.09(12) . . ? N4 Cu1 O1 166.71(11) . . ? C1 O1 Cu1 114.3(3) . . ? C3 N1 C2 117.4(3) . . ? C3 N1 Cu1 128.5(3) . . ? C2 N1 Cu1 113.8(3) . . ? C4 N2 C15 118.2(3) . . ? C4 N2 Cu1 128.2(3) . . ? C15 N2 Cu1 113.6(2) . . ? C13 N3 C14 117.4(4) . . ? C13 N3 Cu1 131.6(3) . . ? C14 N3 Cu1 110.9(3) . . ? C16 N4 C27 117.8(4) . . ? C16 N4 Cu1 132.6(3) . . ? C27 N4 Cu1 109.5(3) . . ? C25 N5 C26 118.3(4) . . ? C25 N5 Cu1 125.8(3) . . ? C26 N5 Cu1 115.5(3) . . ? O2 C1 O1 127.4(4) . . ? O2 C1 C2 115.6(4) . . ? O1 C1 C2 116.9(4) . . ? N1 C2 C3 120.1(4) . 3_755 ? N1 C2 C1 117.4(4) . . ? C3 C2 C1 122.5(4) 3_755 . ? N1 C3 C2 122.5(4) . 3_755 ? N1 C3 H3 118.7 . . ? C2 C3 H3 118.7 3_755 . ? N2 C4 C5 123.1(4) . . ? N2 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? C6 C5 C4 119.5(4) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C7 C15 117.4(4) . . ? C6 C7 C8 124.3(4) . . ? C15 C7 C8 118.2(4) . . ? C9 C8 C7 121.4(4) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 121.9(4) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C14 C10 C11 117.1(4) . . ? C14 C10 C9 118.5(4) . . ? C11 C10 C9 124.4(4) . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 118.8(4) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? N3 C13 C12 123.6(4) . . ? N3 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? N3 C14 C10 123.2(4) . . ? N3 C14 C15 116.7(3) . . ? C10 C14 C15 120.1(4) . . ? N2 C15 C7 122.3(4) . . ? N2 C15 C14 117.9(3) . . ? C7 C15 C14 119.8(4) . . ? N4 C16 C17 122.7(5) . . ? N4 C16 H16 118.6 . . ? C17 C16 H16 118.6 . . ? C18 C17 C16 119.4(5) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.1(5) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C27 116.9(5) . . ? C18 C19 C20 124.1(5) . . ? C27 C19 C20 119.0(5) . . ? C21 C20 C19 121.1(5) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 121.8(5) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C26 C22 C23 117.0(5) . . ? C26 C22 C21 118.0(5) . . ? C23 C22 C21 124.9(5) . . ? C24 C23 C22 120.7(4) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 118.5(5) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? N5 C25 C24 123.4(5) . . ? N5 C25 H25 118.3 . . ? C24 C25 H25 118.3 . . ? N5 C26 C22 122.1(4) . . ? N5 C26 C27 117.8(4) . . ? C22 C26 C27 120.1(4) . . ? N4 C27 C19 123.1(4) . . ? N4 C27 C26 117.0(4) . . ? C19 C27 C26 119.9(4) . . ? O3 N6 O4 124.5(8) . . ? O3 N6 O5 116.1(7) . . ? O4 N6 O5 119.3(7) . . ? H6A O6 H6B 116.0 . . ? H7A O7 H7B 117.1 . . ? H8A O8 H8B 115.8 . . ? H9A O9 H9B 116.0 . . ? H10A O10 H10B 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Cu1 O1 C1 102.4(3) . . . . ? N2 Cu1 O1 C1 -84.7(3) . . . . ? N3 Cu1 O1 C1 -165.5(3) . . . . ? N1 Cu1 O1 C1 11.6(3) . . . . ? N4 Cu1 O1 C1 33.5(6) . . . . ? N5 Cu1 N1 C3 75.7(3) . . . . ? N2 Cu1 N1 C3 -100.7(3) . . . . ? N3 Cu1 N1 C3 -178.7(4) . . . . ? N4 Cu1 N1 C3 -3.9(3) . . . . ? O1 Cu1 N1 C3 171.2(3) . . . . ? N5 Cu1 N1 C2 -98.0(3) . . . . ? N2 Cu1 N1 C2 85.6(3) . . . . ? N3 Cu1 N1 C2 7.6(6) . . . . ? N4 Cu1 N1 C2 -177.6(3) . . . . ? O1 Cu1 N1 C2 -2.5(2) . . . . ? N5 Cu1 N2 C4 -139.4(8) . . . . ? N3 Cu1 N2 C4 -179.6(4) . . . . ? N1 Cu1 N2 C4 16.7(4) . . . . ? N4 Cu1 N2 C4 -76.5(4) . . . . ? O1 Cu1 N2 C4 91.7(4) . . . . ? N5 Cu1 N2 C15 39.0(10) . . . . ? N3 Cu1 N2 C15 -1.3(3) . . . . ? N1 Cu1 N2 C15 -164.9(3) . . . . ? N4 Cu1 N2 C15 101.9(3) . . . . ? O1 Cu1 N2 C15 -89.9(3) . . . . ? N5 Cu1 N3 C13 8.1(4) . . . . ? N2 Cu1 N3 C13 -177.8(4) . . . . ? N1 Cu1 N3 C13 -97.5(5) . . . . ? N4 Cu1 N3 C13 87.7(4) . . . . ? O1 Cu1 N3 C13 -87.8(4) . . . . ? N5 Cu1 N3 C14 -174.4(3) . . . . ? N2 Cu1 N3 C14 -0.2(3) . . . . ? N1 Cu1 N3 C14 80.0(5) . . . . ? N4 Cu1 N3 C14 -94.7(3) . . . . ? O1 Cu1 N3 C14 89.7(3) . . . . ? N5 Cu1 N4 C16 -176.1(4) . . . . ? N2 Cu1 N4 C16 12.1(4) . . . . ? N3 Cu1 N4 C16 94.2(4) . . . . ? N1 Cu1 N4 C16 -84.2(4) . . . . ? O1 Cu1 N4 C16 -105.4(6) . . . . ? N5 Cu1 N4 C27 6.9(2) . . . . ? N2 Cu1 N4 C27 -164.9(2) . . . . ? N3 Cu1 N4 C27 -82.7(3) . . . . ? N1 Cu1 N4 C27 98.8(3) . . . . ? O1 Cu1 N4 C27 77.6(6) . . . . ? N2 Cu1 N5 C25 -116.5(9) . . . . ? N3 Cu1 N5 C25 -76.9(3) . . . . ? N1 Cu1 N5 C25 87.2(3) . . . . ? N4 Cu1 N5 C25 179.4(4) . . . . ? O1 Cu1 N5 C25 12.0(3) . . . . ? N2 Cu1 N5 C26 56.0(10) . . . . ? N3 Cu1 N5 C26 95.6(3) . . . . ? N1 Cu1 N5 C26 -100.3(3) . . . . ? N4 Cu1 N5 C26 -8.1(3) . . . . ? O1 Cu1 N5 C26 -175.5(3) . . . . ? Cu1 O1 C1 O2 159.2(4) . . . . ? Cu1 O1 C1 C2 -18.0(4) . . . . ? C3 N1 C2 C3 -1.0(6) . . . 3_755 ? Cu1 N1 C2 C3 173.5(3) . . . 3_755 ? C3 N1 C2 C1 -179.8(3) . . . . ? Cu1 N1 C2 C1 -5.3(4) . . . . ? O2 C1 C2 N1 -161.2(4) . . . . ? O1 C1 C2 N1 16.3(5) . . . . ? O2 C1 C2 C3 20.0(6) . . . 3_755 ? O1 C1 C2 C3 -162.5(4) . . . 3_755 ? C2 N1 C3 C2 1.0(6) . . . 3_755 ? Cu1 N1 C3 C2 -172.5(3) . . . 3_755 ? C15 N2 C4 C5 0.5(7) . . . . ? Cu1 N2 C4 C5 178.8(4) . . . . ? N2 C4 C5 C6 -0.8(8) . . . . ? C4 C5 C6 C7 1.5(8) . . . . ? C5 C6 C7 C15 -1.7(7) . . . . ? C5 C6 C7 C8 179.0(5) . . . . ? C6 C7 C8 C9 -178.1(5) . . . . ? C15 C7 C8 C9 2.6(7) . . . . ? C7 C8 C9 C10 -1.3(8) . . . . ? C8 C9 C10 C14 -1.5(8) . . . . ? C8 C9 C10 C11 179.5(5) . . . . ? C14 C10 C11 C12 -1.6(7) . . . . ? C9 C10 C11 C12 177.5(5) . . . . ? C10 C11 C12 C13 0.2(8) . . . . ? C14 N3 C13 C12 -1.6(7) . . . . ? Cu1 N3 C13 C12 175.9(3) . . . . ? C11 C12 C13 N3 1.5(8) . . . . ? C13 N3 C14 C10 0.1(6) . . . . ? Cu1 N3 C14 C10 -177.9(3) . . . . ? C13 N3 C14 C15 179.6(4) . . . . ? Cu1 N3 C14 C15 1.7(4) . . . . ? C11 C10 C14 N3 1.5(7) . . . . ? C9 C10 C14 N3 -177.7(4) . . . . ? C11 C10 C14 C15 -178.0(4) . . . . ? C9 C10 C14 C15 2.8(7) . . . . ? C4 N2 C15 C7 -0.8(6) . . . . ? Cu1 N2 C15 C7 -179.3(3) . . . . ? C4 N2 C15 C14 -178.8(4) . . . . ? Cu1 N2 C15 C14 2.6(5) . . . . ? C6 C7 C15 N2 1.4(6) . . . . ? C8 C7 C15 N2 -179.3(4) . . . . ? C6 C7 C15 C14 179.4(4) . . . . ? C8 C7 C15 C14 -1.2(6) . . . . ? N3 C14 C15 N2 -2.9(6) . . . . ? C10 C14 C15 N2 176.7(4) . . . . ? N3 C14 C15 C7 179.0(4) . . . . ? C10 C14 C15 C7 -1.5(6) . . . . ? C27 N4 C16 C17 0.7(6) . . . . ? Cu1 N4 C16 C17 -176.1(3) . . . . ? N4 C16 C17 C18 0.5(8) . . . . ? C16 C17 C18 C19 -0.4(8) . . . . ? C17 C18 C19 C27 -0.7(7) . . . . ? C17 C18 C19 C20 179.5(5) . . . . ? C18 C19 C20 C21 179.4(5) . . . . ? C27 C19 C20 C21 -0.4(7) . . . . ? C19 C20 C21 C22 -0.5(8) . . . . ? C20 C21 C22 C26 -0.3(7) . . . . ? C20 C21 C22 C23 -177.2(5) . . . . ? C26 C22 C23 C24 0.2(7) . . . . ? C21 C22 C23 C24 177.2(4) . . . . ? C22 C23 C24 C25 0.6(7) . . . . ? C26 N5 C25 C24 -1.3(6) . . . . ? Cu1 N5 C25 C24 171.0(3) . . . . ? C23 C24 C25 N5 0.0(7) . . . . ? C25 N5 C26 C22 2.2(6) . . . . ? Cu1 N5 C26 C22 -170.9(3) . . . . ? C25 N5 C26 C27 -178.5(3) . . . . ? Cu1 N5 C26 C27 8.4(4) . . . . ? C23 C22 C26 N5 -1.6(6) . . . . ? C21 C22 C26 N5 -178.8(4) . . . . ? C23 C22 C26 C27 179.1(4) . . . . ? C21 C22 C26 C27 1.9(6) . . . . ? C16 N4 C27 C19 -2.0(6) . . . . ? Cu1 N4 C27 C19 175.5(3) . . . . ? C16 N4 C27 C26 177.8(4) . . . . ? Cu1 N4 C27 C26 -4.7(4) . . . . ? C18 C19 C27 N4 2.0(6) . . . . ? C20 C19 C27 N4 -178.2(4) . . . . ? C18 C19 C27 C26 -177.8(4) . . . . ? C20 C19 C27 C26 2.0(6) . . . . ? N5 C26 C27 N4 -1.9(5) . . . . ? C22 C26 C27 N4 177.4(3) . . . . ? N5 C26 C27 C19 177.9(3) . . . . ? C22 C26 C27 C19 -2.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.444 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.074 # Attachment 'complex 6.cif' data_r71226e _database_code_depnum_ccdc_archive 'CCDC 682362' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Cu2 N8 O18' _chemical_formula_weight 889.65 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 7.0457(14) _cell_length_b 18.245(4) _cell_length_c 12.884(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.89(3) _cell_angle_gamma 90.00 _cell_volume 1636.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3759 _cell_measurement_theta_min 1.599 _cell_measurement_theta_max 27.841 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.398 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8964 _exptl_absorpt_correction_T_max 0.9462 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9925 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2903 _reflns_number_gt 2417 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0392P)^2^+1.7843P] 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 2903 _refine_ls_number_parameters 253 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.088 _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 0.89975(8) 0.07852(3) 0.24684(4) 0.02037(18) Uani 1 1 d . . . O1 O 1.1944(4) 0.02270(17) 0.2621(2) 0.0285(7) Uani 1 1 d . . . O2 O 1.3941(5) -0.05625(18) 0.3516(2) 0.0331(8) Uani 1 1 d . . . O3 O 0.6437(4) 0.09573(17) 0.3227(2) 0.0271(7) Uani 1 1 d . . . O4 O 0.5215(5) 0.09376(18) 0.4700(2) 0.0347(8) Uani 1 1 d D . . H4A H 0.5594 0.0788 0.5328 0.042 Uiso 1 1 d RD . . O5 O 1.0138(4) 0.16942(15) 0.3104(2) 0.0267(7) Uani 1 1 d D . . H5A H 1.1274 0.1706 0.2955 0.032 Uiso 1 1 d RD . . H5B H 1.0035 0.1744 0.3749 0.032 Uiso 1 1 d RD . . O6 O 1.1700(5) 0.13962(17) 0.5571(2) 0.0350(8) Uani 1 1 d . . . O7 O 0.9161(5) 0.20308(19) 0.5023(3) 0.0479(10) Uani 1 1 d . . . O8 O 1.0376(6) 0.2045(2) 0.6671(2) 0.0554(12) Uani 1 1 d . . . O9 O 0.3335(4) 0.17964(17) 0.2309(2) 0.0324(8) Uani 1 1 d D . . H9A H 0.4202 0.1549 0.2697 0.039 Uiso 1 1 d RD . . H9B H 0.3765 0.2167 0.2006 0.039 Uiso 1 1 d RD . . N1 N 0.9579(5) 0.02587(17) 0.4001(2) 0.0158(7) Uani 1 1 d . . . N2 N 0.8668(5) 0.12421(19) 0.1035(2) 0.0218(8) Uani 1 1 d . . . N3 N 0.7904(5) -0.00764(18) 0.1631(2) 0.0194(8) Uani 1 1 d . . . N4 N 1.0390(6) 0.18196(19) 0.5760(3) 0.0283(9) Uani 1 1 d . . . C1 C 1.2462(6) -0.0140(2) 0.3416(3) 0.0208(9) Uani 1 1 d . . . C2 C 1.1254(6) -0.0087(2) 0.4298(3) 0.0180(9) Uani 1 1 d . . . C3 C 0.8316(6) 0.0362(2) 0.4666(3) 0.0184(9) Uani 1 1 d . . . C4 C 0.6532(6) 0.0785(2) 0.4165(3) 0.0214(9) Uani 1 1 d . . . C5 C 0.9010(6) 0.1942(2) 0.0800(3) 0.0269(10) Uani 1 1 d . . . H5 H 0.9383 0.2271 0.1345 0.032 Uiso 1 1 calc R . . C6 C 0.8827(6) 0.2190(2) -0.0227(3) 0.0259(10) Uani 1 1 d . . . H6 H 0.9085 0.2677 -0.0370 0.031 Uiso 1 1 calc R . . C7 C 0.8256(7) 0.1705(3) -0.1033(3) 0.0302(11) Uani 1 1 d . . . H7 H 0.8128 0.1860 -0.1728 0.036 Uiso 1 1 calc R . . C8 C 0.7877(6) 0.0988(2) -0.0803(3) 0.0251(10) Uani 1 1 d . . . H8 H 0.7483 0.0656 -0.1341 0.030 Uiso 1 1 calc R . . C9 C 0.8089(6) 0.0768(2) 0.0233(3) 0.0198(9) Uani 1 1 d . . . C10 C 0.7703(6) 0.0017(2) 0.0573(3) 0.0195(9) Uani 1 1 d . . . C11 C 0.7133(6) -0.0559(2) -0.0118(3) 0.0215(9) Uani 1 1 d . . . H11 H 0.6986 -0.0485 -0.0840 0.026 Uiso 1 1 calc R . . C12 C 0.6792(6) -0.1237(2) 0.0284(3) 0.0247(10) Uani 1 1 d . . . H12 H 0.6437 -0.1629 -0.0166 0.030 Uiso 1 1 calc R . . C13 C 0.6980(6) -0.1332(2) 0.1366(3) 0.0257(10) Uani 1 1 d . . . H13 H 0.6738 -0.1785 0.1650 0.031 Uiso 1 1 calc R . . C14 C 0.7535(6) -0.0738(2) 0.2010(3) 0.0228(10) Uani 1 1 d . . . H14 H 0.7656 -0.0800 0.2734 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0253(3) 0.0189(3) 0.0176(3) -0.0007(2) 0.0056(2) -0.0009(2) O1 0.034(2) 0.0299(17) 0.0232(15) 0.0034(13) 0.0091(13) 0.0003(15) O2 0.034(2) 0.038(2) 0.0299(16) 0.0043(14) 0.0135(14) 0.0098(17) O3 0.0229(18) 0.0356(19) 0.0231(15) 0.0032(13) 0.0042(12) 0.0049(15) O4 0.038(2) 0.042(2) 0.0263(16) 0.0025(14) 0.0116(14) 0.0095(17) O5 0.034(2) 0.0246(17) 0.0244(15) -0.0038(13) 0.0121(13) -0.0065(14) O6 0.039(2) 0.0268(18) 0.0436(19) -0.0065(15) 0.0204(16) -0.0039(17) O7 0.063(3) 0.035(2) 0.0390(19) -0.0033(16) -0.0127(18) 0.011(2) O8 0.080(3) 0.063(3) 0.0241(17) -0.0064(17) 0.0085(17) 0.039(2) O9 0.031(2) 0.0299(18) 0.0357(17) 0.0071(14) 0.0045(14) -0.0027(15) N1 0.016(2) 0.0134(17) 0.0187(16) -0.0016(13) 0.0054(13) -0.0018(15) N2 0.022(2) 0.023(2) 0.0219(17) -0.0007(15) 0.0064(14) 0.0051(16) N3 0.021(2) 0.0208(19) 0.0174(16) -0.0028(14) 0.0051(13) -0.0009(16) N4 0.041(3) 0.018(2) 0.0259(19) 0.0039(16) 0.0041(18) -0.0041(19) C1 0.022(3) 0.018(2) 0.023(2) 0.0000(17) 0.0066(18) 0.000(2) C2 0.019(2) 0.016(2) 0.0201(19) -0.0031(16) 0.0054(16) -0.0035(18) C3 0.021(2) 0.015(2) 0.0203(19) -0.0037(16) 0.0060(17) -0.0051(18) C4 0.017(2) 0.025(2) 0.024(2) -0.0031(18) 0.0072(17) -0.0010(19) C5 0.026(3) 0.026(3) 0.030(2) -0.0012(19) 0.0082(19) 0.004(2) C6 0.023(3) 0.024(2) 0.033(2) 0.0082(19) 0.0113(19) 0.005(2) C7 0.030(3) 0.034(3) 0.027(2) 0.005(2) 0.0095(19) 0.006(2) C8 0.026(3) 0.025(2) 0.024(2) 0.0013(18) 0.0041(18) 0.004(2) C9 0.012(2) 0.024(2) 0.024(2) -0.0006(17) 0.0053(16) 0.0046(19) C10 0.013(2) 0.022(2) 0.024(2) 0.0045(17) 0.0058(16) 0.0056(19) C11 0.018(2) 0.024(2) 0.022(2) -0.0027(17) 0.0032(17) 0.0004(19) C12 0.023(3) 0.024(2) 0.027(2) -0.0063(18) 0.0011(18) 0.000(2) C13 0.027(3) 0.022(2) 0.029(2) 0.0002(18) 0.0067(19) -0.002(2) C14 0.023(3) 0.026(2) 0.019(2) 0.0026(17) 0.0027(17) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.966(3) . ? Cu1 N3 1.993(3) . ? Cu1 N2 2.006(3) . ? Cu1 N1 2.177(3) . ? Cu1 O3 2.203(3) . ? Cu1 O1 2.294(3) . ? O1 C1 1.231(5) . ? O2 C1 1.287(5) . ? O3 C4 1.241(5) . ? O4 C4 1.269(5) . ? O4 H4A 0.8565 . ? O5 H5A 0.8511 . ? O5 H5B 0.8504 . ? O6 N4 1.256(5) . ? O7 N4 1.244(5) . ? O8 N4 1.244(5) . ? O9 H9A 0.8564 . ? O9 H9B 0.8582 . ? N1 C2 1.340(5) . ? N1 C3 1.341(5) . ? N2 C5 1.342(6) . ? N2 C9 1.361(5) . ? N3 C14 1.342(5) . ? N3 C10 1.360(5) . ? C1 C2 1.524(5) . ? C2 C3 1.414(5) 3_756 ? C3 C2 1.414(5) 3_756 ? C3 C4 1.530(6) . ? C5 C6 1.386(6) . ? C5 H5 0.9300 . ? C6 C7 1.377(6) . ? C6 H6 0.9300 . ? C7 C8 1.376(6) . ? C7 H7 0.9300 . ? C8 C9 1.381(6) . ? C8 H8 0.9300 . ? C9 C10 1.476(6) . ? C10 C11 1.394(6) . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 C13 1.391(6) . ? C12 H12 0.9300 . ? C13 C14 1.384(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 N3 171.90(12) . . ? O5 Cu1 N2 90.82(13) . . ? N3 Cu1 N2 81.35(14) . . ? O5 Cu1 N1 89.25(12) . . ? N3 Cu1 N1 98.39(13) . . ? N2 Cu1 N1 175.42(13) . . ? O5 Cu1 O3 90.29(12) . . ? N3 Cu1 O3 94.47(13) . . ? N2 Cu1 O3 111.28(13) . . ? N1 Cu1 O3 73.30(11) . . ? O5 Cu1 O1 91.87(12) . . ? N3 Cu1 O1 88.01(13) . . ? N2 Cu1 O1 103.75(12) . . ? N1 Cu1 O1 71.67(11) . . ? O3 Cu1 O1 144.87(10) . . ? C1 O1 Cu1 117.4(3) . . ? C4 O3 Cu1 118.1(3) . . ? C4 O4 H4A 107.2 . . ? Cu1 O5 H5A 105.4 . . ? Cu1 O5 H5B 114.0 . . ? H5A O5 H5B 116.3 . . ? H9A O9 H9B 114.3 . . ? C2 N1 C3 121.7(3) . . ? C2 N1 Cu1 120.0(2) . . ? C3 N1 Cu1 117.9(3) . . ? C5 N2 C9 118.5(3) . . ? C5 N2 Cu1 127.1(3) . . ? C9 N2 Cu1 114.4(3) . . ? C14 N3 C10 118.8(3) . . ? C14 N3 Cu1 126.4(3) . . ? C10 N3 Cu1 114.6(3) . . ? O7 N4 O8 120.8(4) . . ? O7 N4 O6 119.2(4) . . ? O8 N4 O6 119.9(4) . . ? O1 C1 O2 122.7(4) . . ? O1 C1 C2 117.3(4) . . ? O2 C1 C2 120.0(3) . . ? N1 C2 C3 119.1(4) . 3_756 ? N1 C2 C1 112.7(3) . . ? C3 C2 C1 128.2(4) 3_756 . ? N1 C3 C2 119.1(4) . 3_756 ? N1 C3 C4 112.6(3) . . ? C2 C3 C4 128.2(4) 3_756 . ? O3 C4 O4 122.6(4) . . ? O3 C4 C3 117.1(3) . . ? O4 C4 C3 120.2(3) . . ? N2 C5 C6 122.2(4) . . ? N2 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C7 C6 C5 118.9(4) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C8 C7 C6 119.5(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.3(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? N2 C9 C8 121.6(4) . . ? N2 C9 C10 114.4(3) . . ? C8 C9 C10 124.0(4) . . ? N3 C10 C11 121.4(4) . . ? N3 C10 C9 114.7(4) . . ? C11 C10 C9 123.9(4) . . ? C12 C11 C10 119.1(4) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 119.6(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 118.5(4) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? N3 C14 C13 122.6(4) . . ? N3 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 O1 C1 93.1(3) . . . . ? N3 Cu1 O1 C1 -95.0(3) . . . . ? N2 Cu1 O1 C1 -175.6(3) . . . . ? N1 Cu1 O1 C1 4.5(3) . . . . ? O3 Cu1 O1 C1 -0.1(4) . . . . ? O5 Cu1 O3 C4 -80.1(3) . . . . ? N3 Cu1 O3 C4 106.4(3) . . . . ? N2 Cu1 O3 C4 -171.1(3) . . . . ? N1 Cu1 O3 C4 9.0(3) . . . . ? O1 Cu1 O3 C4 13.5(4) . . . . ? O5 Cu1 N1 C2 -90.0(3) . . . . ? N3 Cu1 N1 C2 87.3(3) . . . . ? N2 Cu1 N1 C2 0.9(18) . . . . ? O3 Cu1 N1 C2 179.5(3) . . . . ? O1 Cu1 N1 C2 2.2(3) . . . . ? O5 Cu1 N1 C3 82.9(3) . . . . ? N3 Cu1 N1 C3 -99.8(3) . . . . ? N2 Cu1 N1 C3 173.8(16) . . . . ? O3 Cu1 N1 C3 -7.7(3) . . . . ? O1 Cu1 N1 C3 175.1(3) . . . . ? O5 Cu1 N2 C5 -5.8(4) . . . . ? N3 Cu1 N2 C5 176.3(4) . . . . ? N1 Cu1 N2 C5 -96.6(17) . . . . ? O3 Cu1 N2 C5 84.8(4) . . . . ? O1 Cu1 N2 C5 -97.9(4) . . . . ? O5 Cu1 N2 C9 172.1(3) . . . . ? N3 Cu1 N2 C9 -5.9(3) . . . . ? N1 Cu1 N2 C9 81.2(17) . . . . ? O3 Cu1 N2 C9 -97.3(3) . . . . ? O1 Cu1 N2 C9 79.9(3) . . . . ? O5 Cu1 N3 C14 165.9(8) . . . . ? N2 Cu1 N3 C14 -179.1(4) . . . . ? N1 Cu1 N3 C14 5.5(4) . . . . ? O3 Cu1 N3 C14 -68.3(4) . . . . ? O1 Cu1 N3 C14 76.6(4) . . . . ? O5 Cu1 N3 C10 -7.5(11) . . . . ? N2 Cu1 N3 C10 7.4(3) . . . . ? N1 Cu1 N3 C10 -168.0(3) . . . . ? O3 Cu1 N3 C10 118.3(3) . . . . ? O1 Cu1 N3 C10 -96.8(3) . . . . ? Cu1 O1 C1 O2 169.4(3) . . . . ? Cu1 O1 C1 C2 -9.7(5) . . . . ? C3 N1 C2 C3 1.2(6) . . . 3_756 ? Cu1 N1 C2 C3 173.8(3) . . . 3_756 ? C3 N1 C2 C1 -179.8(3) . . . . ? Cu1 N1 C2 C1 -7.2(4) . . . . ? O1 C1 C2 N1 11.2(5) . . . . ? O2 C1 C2 N1 -167.9(4) . . . . ? O1 C1 C2 C3 -169.9(4) . . . 3_756 ? O2 C1 C2 C3 11.0(6) . . . 3_756 ? C2 N1 C3 C2 -1.2(6) . . . 3_756 ? Cu1 N1 C3 C2 -173.9(3) . . . 3_756 ? C2 N1 C3 C4 178.6(3) . . . . ? Cu1 N1 C3 C4 5.9(4) . . . . ? Cu1 O3 C4 O4 172.0(3) . . . . ? Cu1 O3 C4 C3 -8.9(5) . . . . ? N1 C3 C4 O3 2.0(5) . . . . ? C2 C3 C4 O3 -178.2(4) 3_756 . . . ? N1 C3 C4 O4 -178.8(4) . . . . ? C2 C3 C4 O4 1.0(7) 3_756 . . . ? C9 N2 C5 C6 -1.2(6) . . . . ? Cu1 N2 C5 C6 176.6(3) . . . . ? N2 C5 C6 C7 0.7(7) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? C6 C7 C8 C9 -0.4(7) . . . . ? C5 N2 C9 C8 0.9(6) . . . . ? Cu1 N2 C9 C8 -177.1(3) . . . . ? C5 N2 C9 C10 -178.5(4) . . . . ? Cu1 N2 C9 C10 3.4(4) . . . . ? C7 C8 C9 N2 -0.1(6) . . . . ? C7 C8 C9 C10 179.3(4) . . . . ? C14 N3 C10 C11 -0.2(6) . . . . ? Cu1 N3 C10 C11 173.8(3) . . . . ? C14 N3 C10 C9 178.4(4) . . . . ? Cu1 N3 C10 C9 -7.6(5) . . . . ? N2 C9 C10 N3 2.7(5) . . . . ? C8 C9 C10 N3 -176.7(4) . . . . ? N2 C9 C10 C11 -178.7(4) . . . . ? C8 C9 C10 C11 1.9(7) . . . . ? N3 C10 C11 C12 -0.9(6) . . . . ? C9 C10 C11 C12 -179.3(4) . . . . ? C10 C11 C12 C13 1.4(6) . . . . ? C11 C12 C13 C14 -0.8(6) . . . . ? C10 N3 C14 C13 0.8(6) . . . . ? Cu1 N3 C14 C13 -172.4(3) . . . . ? C12 C13 C14 N3 -0.3(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.581 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.091 # Attachment 'complex 7.cif' data_r071029e _database_code_depnum_ccdc_archive 'CCDC 682363' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Cd N4 O6' _chemical_formula_weight 494.73 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' Cd Cd -0.8075 1.2024 '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 7.7443(15) _cell_length_b 10.237(2) _cell_length_c 11.806(2) _cell_angle_alpha 104.08(3) _cell_angle_beta 102.11(3) _cell_angle_gamma 93.61(3) _cell_volume 881.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2291 _cell_measurement_theta_min 2.372 _cell_measurement_theta_max 27.888 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.865 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.287 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8609 _exptl_absorpt_correction_T_max 0.9041 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6635 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3056 _reflns_number_gt 2597 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0911P)^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 SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3056 _refine_ls_number_parameters 263 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.115 _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 Cd1 Cd 0.31534(4) 0.82946(3) 0.10868(3) 0.0151(2) Uani 1 1 d . . . O1 O 0.2939(5) 0.5880(4) 0.1054(3) 0.0221(9) Uani 1 1 d . . . O2 O 0.2014(5) 0.3745(4) -0.0040(4) 0.0217(9) Uani 1 1 d . . . O3 O 0.2233(5) 0.9559(3) -0.0430(3) 0.0180(8) Uani 1 1 d . . . O4 O 0.0879(5) 0.9407(3) -0.2352(3) 0.0197(8) Uani 1 1 d . . . O5 O 0.0455(5) 0.8247(4) 0.1598(3) 0.0164(8) Uani 1 1 d D . . H5A H 0.0049 0.8997 0.1806 0.020 Uiso 1 1 d RD . . H5B H -0.0294 0.7537 0.1334 0.020 Uiso 1 1 d RD . . O6 O 0.5613(5) 0.8161(4) 0.0273(4) 0.0236(9) Uani 1 1 d D . . H6A H 0.6140 0.7489 0.0396 0.028 Uiso 1 1 d RD . . H6B H 0.6255 0.8921 0.0431 0.028 Uiso 1 1 d RD . . N1 N 0.1779(5) 0.6868(4) -0.0818(4) 0.0131(9) Uani 1 1 d . . . N2 N 0.0346(6) 0.5179(4) -0.3108(4) 0.0225(11) Uani 1 1 d . . . N3 N 0.5252(6) 0.8408(4) 0.2900(4) 0.0180(10) Uani 1 1 d . . . N4 N 0.3871(5) 1.0599(4) 0.2269(4) 0.0149(10) Uani 1 1 d . . . C1 C 0.2235(7) 0.5002(5) 0.0084(5) 0.0196(12) Uani 1 1 d . . . C2 C 0.1582(6) 0.5517(5) -0.1011(5) 0.0129(11) Uani 1 1 d . . . C3 C 0.0842(7) 0.4690(5) -0.2159(5) 0.0207(12) Uani 1 1 d . . . H3 H 0.0687 0.3755 -0.2267 0.025 Uiso 1 1 calc R . . C4 C 0.0551(7) 0.6523(5) -0.2909(5) 0.0209(12) Uani 1 1 d . . . H4 H 0.0217 0.6903 -0.3551 0.025 Uiso 1 1 calc R . . C5 C 0.1259(6) 0.7381(5) -0.1757(4) 0.0141(11) Uani 1 1 d . . . C6 C 0.1485(7) 0.8914(5) -0.1487(5) 0.0155(11) Uani 1 1 d . . . C7 C 0.5908(7) 0.7337(6) 0.3191(5) 0.0195(12) Uani 1 1 d . . . H7 H 0.5463 0.6478 0.2690 0.023 Uiso 1 1 calc R . . C8 C 0.7254(8) 0.7453(6) 0.4230(6) 0.0286(14) Uani 1 1 d . . . H8 H 0.7687 0.6678 0.4401 0.034 Uiso 1 1 calc R . . C9 C 0.7933(7) 0.8714(6) 0.4995(5) 0.0215(12) Uani 1 1 d . . . H9 H 0.8797 0.8803 0.5697 0.026 Uiso 1 1 calc R . . C10 C 0.7272(7) 0.9869(6) 0.4676(4) 0.0167(11) Uani 1 1 d . . . C11 C 0.7910(7) 1.1225(6) 0.5380(5) 0.0233(13) Uani 1 1 d . . . H11 H 0.8783 1.1361 0.6085 0.028 Uiso 1 1 calc R . . C12 C 0.7291(8) 1.2308(6) 0.5059(5) 0.0294(15) Uani 1 1 d . . . H12 H 0.7758 1.3176 0.5531 0.035 Uiso 1 1 calc R . . C13 C 0.5910(7) 1.2138(5) 0.3989(5) 0.0204(12) Uani 1 1 d . . . C14 C 0.5190(7) 1.3242(6) 0.3637(5) 0.0250(13) Uani 1 1 d . . . H14 H 0.5641 1.4125 0.4078 0.030 Uiso 1 1 calc R . . C15 C 0.3833(8) 1.3012(5) 0.2648(5) 0.0243(13) Uani 1 1 d . . . H15 H 0.3338 1.3734 0.2409 0.029 Uiso 1 1 calc R . . C16 C 0.3185(7) 1.1668(5) 0.1990(5) 0.0206(12) Uani 1 1 d . . . H16 H 0.2231 1.1521 0.1329 0.025 Uiso 1 1 calc R . . C17 C 0.5197(6) 1.0820(5) 0.3255(5) 0.0163(11) Uani 1 1 d . . . C18 C 0.5943(6) 0.9658(5) 0.3624(4) 0.0159(11) 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 Cd1 0.0143(3) 0.0108(3) 0.0179(3) 0.00210(18) 0.00155(18) -0.00018(17) O1 0.025(2) 0.0142(19) 0.022(2) 0.0061(16) -0.0066(17) 0.0024(16) O2 0.025(2) 0.0097(18) 0.029(2) 0.0036(16) 0.0071(18) 0.0002(16) O3 0.0239(19) 0.0125(18) 0.0140(19) 0.0016(15) -0.0003(16) 0.0001(15) O4 0.029(2) 0.0130(18) 0.017(2) 0.0006(16) 0.0070(17) 0.0034(16) O5 0.0163(18) 0.0129(18) 0.0191(19) 0.0055(15) 0.0003(15) 0.0018(15) O6 0.0205(19) 0.0116(18) 0.042(3) 0.0071(17) 0.0149(19) 0.0012(15) N1 0.010(2) 0.014(2) 0.014(2) 0.0026(18) 0.0007(17) 0.0005(18) N2 0.030(3) 0.014(2) 0.021(3) 0.004(2) 0.000(2) -0.002(2) N3 0.014(2) 0.017(2) 0.020(2) 0.0005(19) 0.0020(19) -0.0009(18) N4 0.015(2) 0.020(2) 0.008(2) 0.0035(18) -0.0012(18) -0.0010(18) C1 0.013(3) 0.010(3) 0.034(3) 0.001(2) 0.008(2) 0.000(2) C2 0.007(2) 0.013(2) 0.015(3) 0.002(2) -0.002(2) 0.000(2) C3 0.021(3) 0.015(3) 0.023(3) 0.004(2) -0.001(2) 0.001(2) C4 0.019(3) 0.022(3) 0.020(3) 0.007(2) -0.001(2) 0.002(2) C5 0.012(2) 0.014(3) 0.011(3) -0.003(2) 0.002(2) -0.002(2) C6 0.019(3) 0.013(3) 0.017(3) 0.004(2) 0.009(2) 0.002(2) C7 0.017(3) 0.028(3) 0.008(3) 0.003(2) -0.007(2) 0.003(2) C8 0.028(3) 0.025(3) 0.040(4) 0.012(3) 0.017(3) 0.008(3) C9 0.016(3) 0.035(3) 0.015(3) 0.009(2) 0.005(2) 0.004(2) C10 0.015(2) 0.030(3) 0.005(2) 0.006(2) 0.001(2) 0.003(2) C11 0.024(3) 0.031(3) 0.006(2) -0.009(2) 0.001(2) -0.007(2) C12 0.036(3) 0.017(3) 0.030(3) -0.010(3) 0.018(3) -0.008(3) C13 0.017(3) 0.020(3) 0.020(3) -0.004(2) 0.009(2) -0.005(2) C14 0.027(3) 0.020(3) 0.025(3) -0.003(2) 0.013(3) -0.005(2) C15 0.029(3) 0.015(3) 0.031(3) 0.005(2) 0.012(3) 0.002(2) C16 0.017(3) 0.020(3) 0.026(3) 0.007(2) 0.006(2) 0.003(2) C17 0.012(2) 0.022(3) 0.015(3) 0.004(2) 0.005(2) 0.000(2) C18 0.010(2) 0.027(3) 0.009(3) 0.004(2) 0.000(2) -0.001(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 Cd1 O5 2.294(4) . ? Cd1 O6 2.304(4) . ? Cd1 N1 2.351(4) . ? Cd1 N3 2.374(4) . ? Cd1 N4 2.393(4) . ? Cd1 O1 2.458(3) . ? Cd1 O3 2.469(4) . ? O1 C1 1.261(6) . ? O2 C1 1.256(6) . ? O3 C6 1.255(6) . ? O4 C6 1.264(6) . ? O5 H5A 0.8485 . ? O5 H5B 0.8500 . ? O6 H6A 0.8491 . ? O6 H6B 0.8533 . ? N1 C5 1.337(6) . ? N1 C2 1.339(6) . ? N2 C3 1.331(7) . ? N2 C4 1.332(7) . ? N3 C7 1.326(7) . ? N3 C18 1.357(7) . ? N4 C16 1.328(7) . ? N4 C17 1.342(6) . ? C1 C2 1.515(8) . ? C2 C3 1.392(7) . ? C3 H3 0.9300 . ? C4 C5 1.403(7) . ? C4 H4 0.9300 . ? C5 C6 1.515(7) . ? C7 C8 1.408(8) . ? C7 H7 0.9300 . ? C8 C9 1.381(8) . ? C8 H8 0.9300 . ? C9 C10 1.419(7) . ? C9 H9 0.9300 . ? C10 C18 1.398(7) . ? C10 C11 1.429(7) . ? C11 C12 1.341(8) . ? C11 H11 0.9300 . ? C12 C13 1.439(8) . ? C12 H12 0.9300 . ? C13 C14 1.404(8) . ? C13 C17 1.419(7) . ? C14 C15 1.358(8) . ? C14 H14 0.9300 . ? C15 C16 1.406(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.474(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cd1 O6 170.93(12) . . ? O5 Cd1 N1 89.15(13) . . ? O6 Cd1 N1 81.86(14) . . ? O5 Cd1 N3 104.35(14) . . ? O6 Cd1 N3 83.77(15) . . ? N1 Cd1 N3 143.56(15) . . ? O5 Cd1 N4 89.06(14) . . ? O6 Cd1 N4 97.62(14) . . ? N1 Cd1 N4 144.95(14) . . ? N3 Cd1 N4 70.17(15) . . ? O5 Cd1 O1 85.06(13) . . ? O6 Cd1 O1 92.48(13) . . ? N1 Cd1 O1 67.19(13) . . ? N3 Cd1 O1 80.22(14) . . ? N4 Cd1 O1 147.32(14) . . ? O5 Cd1 O3 93.96(12) . . ? O6 Cd1 O3 81.52(13) . . ? N1 Cd1 O3 67.16(12) . . ? N3 Cd1 O3 142.69(13) . . ? N4 Cd1 O3 78.06(13) . . ? O1 Cd1 O3 134.35(12) . . ? C1 O1 Cd1 119.4(3) . . ? C6 O3 Cd1 119.2(3) . . ? Cd1 O5 H5A 117.7 . . ? Cd1 O5 H5B 120.9 . . ? H5A O5 H5B 117.0 . . ? Cd1 O6 H6A 110.5 . . ? Cd1 O6 H6B 113.5 . . ? H6A O6 H6B 117.3 . . ? C5 N1 C2 118.0(4) . . ? C5 N1 Cd1 120.8(3) . . ? C2 N1 Cd1 121.1(3) . . ? C3 N2 C4 116.7(5) . . ? C7 N3 C18 118.2(5) . . ? C7 N3 Cd1 123.9(3) . . ? C18 N3 Cd1 117.6(3) . . ? C16 N4 C17 117.9(5) . . ? C16 N4 Cd1 126.2(3) . . ? C17 N4 Cd1 115.6(3) . . ? O2 C1 O1 125.3(5) . . ? O2 C1 C2 117.8(5) . . ? O1 C1 C2 117.0(4) . . ? N1 C2 C3 120.1(5) . . ? N1 C2 C1 115.3(4) . . ? C3 C2 C1 124.5(5) . . ? N2 C3 C2 122.8(5) . . ? N2 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? N2 C4 C5 121.7(5) . . ? N2 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? N1 C5 C4 120.7(5) . . ? N1 C5 C6 115.9(4) . . ? C4 C5 C6 123.4(5) . . ? O3 C6 O4 127.0(5) . . ? O3 C6 C5 116.8(5) . . ? O4 C6 C5 116.2(4) . . ? N3 C7 C8 122.4(5) . . ? N3 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C9 C8 C7 120.1(5) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 117.9(5) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? C18 C10 C9 118.0(5) . . ? C18 C10 C11 119.1(5) . . ? C9 C10 C11 122.9(5) . . ? C12 C11 C10 122.2(5) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C13 120.6(5) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C17 117.2(5) . . ? C14 C13 C12 122.4(5) . . ? C17 C13 C12 120.3(5) . . ? C15 C14 C13 119.6(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.1(5) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N4 C16 C15 123.1(5) . . ? N4 C16 H16 118.4 . . ? C15 C16 H16 118.4 . . ? N4 C17 C13 122.9(5) . . ? N4 C17 C18 119.6(5) . . ? C13 C17 C18 117.5(5) . . ? N3 C18 C10 123.3(5) . . ? N3 C18 C17 116.3(4) . . ? C10 C18 C17 120.3(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cd1 O1 C1 91.5(4) . . . . ? O6 Cd1 O1 C1 -79.8(4) . . . . ? N1 Cd1 O1 C1 0.3(4) . . . . ? N3 Cd1 O1 C1 -163.0(4) . . . . ? N4 Cd1 O1 C1 171.9(3) . . . . ? O3 Cd1 O1 C1 0.7(5) . . . . ? O5 Cd1 O3 C6 -87.5(4) . . . . ? O6 Cd1 O3 C6 84.5(4) . . . . ? N1 Cd1 O3 C6 -0.1(4) . . . . ? N3 Cd1 O3 C6 152.4(3) . . . . ? N4 Cd1 O3 C6 -175.7(4) . . . . ? O1 Cd1 O3 C6 -0.6(4) . . . . ? O5 Cd1 N1 C5 97.2(4) . . . . ? O6 Cd1 N1 C5 -81.6(4) . . . . ? N3 Cd1 N1 C5 -149.4(3) . . . . ? N4 Cd1 N1 C5 10.1(5) . . . . ? O1 Cd1 N1 C5 -177.8(4) . . . . ? O3 Cd1 N1 C5 2.6(3) . . . . ? O5 Cd1 N1 C2 -86.4(4) . . . . ? O6 Cd1 N1 C2 94.7(4) . . . . ? N3 Cd1 N1 C2 27.0(5) . . . . ? N4 Cd1 N1 C2 -173.6(3) . . . . ? O1 Cd1 N1 C2 -1.4(3) . . . . ? O3 Cd1 N1 C2 178.9(4) . . . . ? O5 Cd1 N3 C7 96.4(4) . . . . ? O6 Cd1 N3 C7 -79.5(4) . . . . ? N1 Cd1 N3 C7 -12.3(5) . . . . ? N4 Cd1 N3 C7 -179.9(4) . . . . ? O1 Cd1 N3 C7 14.1(4) . . . . ? O3 Cd1 N3 C7 -146.7(4) . . . . ? O5 Cd1 N3 C18 -90.2(4) . . . . ? O6 Cd1 N3 C18 93.9(4) . . . . ? N1 Cd1 N3 C18 161.1(3) . . . . ? N4 Cd1 N3 C18 -6.5(3) . . . . ? O1 Cd1 N3 C18 -172.5(4) . . . . ? O3 Cd1 N3 C18 26.8(5) . . . . ? O5 Cd1 N4 C16 -72.7(4) . . . . ? O6 Cd1 N4 C16 101.1(4) . . . . ? N1 Cd1 N4 C16 14.4(5) . . . . ? N3 Cd1 N4 C16 -178.4(4) . . . . ? O1 Cd1 N4 C16 -152.1(4) . . . . ? O3 Cd1 N4 C16 21.5(4) . . . . ? O5 Cd1 N4 C17 113.0(3) . . . . ? O6 Cd1 N4 C17 -73.2(4) . . . . ? N1 Cd1 N4 C17 -159.8(3) . . . . ? N3 Cd1 N4 C17 7.3(3) . . . . ? O1 Cd1 N4 C17 33.6(5) . . . . ? O3 Cd1 N4 C17 -152.8(4) . . . . ? Cd1 O1 C1 O2 -178.3(4) . . . . ? Cd1 O1 C1 C2 0.7(6) . . . . ? C5 N1 C2 C3 -0.5(7) . . . . ? Cd1 N1 C2 C3 -176.9(4) . . . . ? C5 N1 C2 C1 178.7(4) . . . . ? Cd1 N1 C2 C1 2.3(6) . . . . ? O2 C1 C2 N1 177.2(4) . . . . ? O1 C1 C2 N1 -1.9(7) . . . . ? O2 C1 C2 C3 -3.7(8) . . . . ? O1 C1 C2 C3 177.2(5) . . . . ? C4 N2 C3 C2 -1.6(8) . . . . ? N1 C2 C3 N2 1.8(8) . . . . ? C1 C2 C3 N2 -177.3(5) . . . . ? C3 N2 C4 C5 0.2(8) . . . . ? C2 N1 C5 C4 -0.9(7) . . . . ? Cd1 N1 C5 C4 175.6(4) . . . . ? C2 N1 C5 C6 179.1(4) . . . . ? Cd1 N1 C5 C6 -4.5(6) . . . . ? N2 C4 C5 N1 1.1(8) . . . . ? N2 C4 C5 C6 -178.9(5) . . . . ? Cd1 O3 C6 O4 177.2(4) . . . . ? Cd1 O3 C6 C5 -1.9(6) . . . . ? N1 C5 C6 O3 4.2(7) . . . . ? C4 C5 C6 O3 -175.9(5) . . . . ? N1 C5 C6 O4 -175.1(4) . . . . ? C4 C5 C6 O4 4.9(7) . . . . ? C18 N3 C7 C8 1.5(8) . . . . ? Cd1 N3 C7 C8 174.9(4) . . . . ? N3 C7 C8 C9 0.5(8) . . . . ? C7 C8 C9 C10 -2.0(8) . . . . ? C8 C9 C10 C18 1.6(7) . . . . ? C8 C9 C10 C11 -178.2(5) . . . . ? C18 C10 C11 C12 -0.8(8) . . . . ? C9 C10 C11 C12 179.0(5) . . . . ? C10 C11 C12 C13 1.5(8) . . . . ? C11 C12 C13 C14 178.3(5) . . . . ? C11 C12 C13 C17 -0.6(8) . . . . ? C17 C13 C14 C15 1.9(8) . . . . ? C12 C13 C14 C15 -177.0(5) . . . . ? C13 C14 C15 C16 -0.5(8) . . . . ? C17 N4 C16 C15 2.8(8) . . . . ? Cd1 N4 C16 C15 -171.4(4) . . . . ? C14 C15 C16 N4 -1.9(8) . . . . ? C16 N4 C17 C13 -1.3(7) . . . . ? Cd1 N4 C17 C13 173.5(4) . . . . ? C16 N4 C17 C18 177.4(5) . . . . ? Cd1 N4 C17 C18 -7.8(6) . . . . ? C14 C13 C17 N4 -1.0(8) . . . . ? C12 C13 C17 N4 177.8(5) . . . . ? C14 C13 C17 C18 -179.7(4) . . . . ? C12 C13 C17 C18 -0.8(7) . . . . ? C7 N3 C18 C10 -1.9(7) . . . . ? Cd1 N3 C18 C10 -175.7(4) . . . . ? C7 N3 C18 C17 178.9(4) . . . . ? Cd1 N3 C18 C17 5.1(6) . . . . ? C9 C10 C18 N3 0.3(7) . . . . ? C11 C10 C18 N3 -179.8(5) . . . . ? C9 C10 C18 C17 179.5(5) . . . . ? C11 C10 C18 C17 -0.6(7) . . . . ? N4 C17 C18 N3 2.0(7) . . . . ? C13 C17 C18 N3 -179.3(4) . . . . ? N4 C17 C18 C10 -177.3(4) . . . . ? C13 C17 C18 C10 1.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.743 _refine_diff_density_min -1.397 _refine_diff_density_rms 0.177 # Attachment 'complex 8.cif' data_r71104e1 _database_code_depnum_ccdc_archive 'CCDC 705533' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cd N4 O6' _chemical_formula_weight 470.71 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' Cd Cd -0.8075 1.2024 '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 7.3378(15) _cell_length_b 10.694(2) _cell_length_c 11.744(2) _cell_angle_alpha 114.24(3) _cell_angle_beta 103.29(3) _cell_angle_gamma 93.40(3) _cell_volume 805.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2537 _cell_measurement_theta_min 2.173 _cell_measurement_theta_max 27.861 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 1.402 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8725 _exptl_absorpt_correction_T_max 0.8961 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4944 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2816 _reflns_number_gt 2584 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0341P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2816 _refine_ls_number_parameters 260 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0535 _refine_ls_wR_factor_gt 0.0529 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 Cd1 Cd 0.15058(2) 0.168578(15) 0.883986(14) 0.01348(7) Uani 1 1 d . . . O1 O 0.1917(2) 0.40895(16) 0.91826(16) 0.0199(4) Uani 1 1 d . . . O2 O 0.3200(2) 0.62502(15) 1.04939(16) 0.0177(4) Uani 1 1 d . . . O3 O 0.2607(2) 0.04054(15) 1.02018(15) 0.0173(3) Uani 1 1 d . . . O4 O 0.4228(2) 0.06827(16) 1.20778(15) 0.0193(4) Uani 1 1 d . . . O5 O 0.4227(2) 0.15481(16) 0.80293(16) 0.0162(3) Uani 1 1 d D . . O6 O -0.0890(2) 0.20354(17) 0.99300(16) 0.0171(3) Uani 1 1 d D . . N1 N 0.3342(2) 0.31233(18) 1.08346(18) 0.0121(4) Uani 1 1 d . . . N2 N 0.5540(3) 0.4872(2) 1.3150(2) 0.0221(4) Uani 1 1 d . . . N3 N -0.0597(3) 0.16154(19) 0.70374(18) 0.0164(4) Uani 1 1 d . . . N4 N 0.0433(2) -0.06224(19) 0.73522(18) 0.0145(4) Uani 1 1 d . . . C1 C 0.2863(3) 0.4977(2) 1.0194(2) 0.0140(5) Uani 1 1 d . . . C2 C 0.3728(3) 0.4475(2) 1.1154(2) 0.0132(5) Uani 1 1 d . . . C3 C 0.4854(3) 0.5334(2) 1.2299(2) 0.0204(5) Uani 1 1 d . . . H3 H 0.5164 0.6272 1.2503 0.024 Uiso 1 1 calc R . . C4 C 0.5113(3) 0.3525(2) 1.2817(2) 0.0206(5) Uani 1 1 d . . . H4 H 0.5592 0.3196 1.3425 0.025 Uiso 1 1 calc R . . C5 C 0.4044(3) 0.2638(2) 1.1666(2) 0.0137(5) Uani 1 1 d . . . C6 C 0.3589(3) 0.1104(2) 1.1276(2) 0.0138(5) Uani 1 1 d . . . C7 C -0.1003(3) 0.2748(3) 0.6879(2) 0.0210(5) Uani 1 1 d . . . H7 H -0.0389 0.3617 0.7536 0.025 Uiso 1 1 calc R . . C8 C -0.2223(3) 0.2692(3) 0.5843(2) 0.0220(5) Uani 1 1 d . . . H8 H -0.2497 0.3491 0.5755 0.026 Uiso 1 1 calc R . . C9 C -0.3049(3) 0.1415(3) 0.4921(2) 0.0205(5) Uani 1 1 d . . . H9 H -0.3915 0.1317 0.4161 0.025 Uiso 1 1 calc R . . C10 C -0.2641(3) 0.0243(3) 0.5073(2) 0.0185(5) Uani 1 1 d . . . H10 H -0.3228 -0.0635 0.4421 0.022 Uiso 1 1 calc R . . C11 C -0.1419(3) 0.0368(2) 0.6145(2) 0.0152(5) Uani 1 1 d . . . C12 C -0.0925(3) -0.0856(2) 0.6353(2) 0.0148(5) Uani 1 1 d . . . C13 C -0.1780(3) -0.2185(3) 0.5556(2) 0.0206(5) Uani 1 1 d . . . H13 H -0.2770 -0.2358 0.4826 0.025 Uiso 1 1 calc R . . C14 C -0.1247(3) -0.3290(3) 0.5780(2) 0.0227(5) Uani 1 1 d . . . H14 H -0.1884 -0.4192 0.5222 0.027 Uiso 1 1 calc R . . C15 C 0.0158(3) -0.3060(2) 0.6780(2) 0.0212(5) Uani 1 1 d . . . H15 H 0.0582 -0.3776 0.6965 0.025 Uiso 1 1 calc R . . C16 C 0.0967(3) -0.1713(2) 0.7536(2) 0.0178(5) Uani 1 1 d . . . H16 H 0.1991 -0.1528 0.8251 0.021 Uiso 1 1 calc R . . H5A H 0.468(3) 0.0819(14) 0.800(2) 0.018(7) Uiso 1 1 d D . . H5B H 0.505(3) 0.2301(14) 0.846(2) 0.040(9) Uiso 1 1 d D . . H6A H -0.153(3) 0.2644(19) 0.989(3) 0.029(8) Uiso 1 1 d D . . H6B H -0.146(3) 0.1260(15) 0.980(3) 0.042(9) Uiso 1 1 d 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 Cd1 0.01276(11) 0.01064(11) 0.01067(11) 0.00314(7) -0.00439(7) -0.00217(7) O1 0.0208(9) 0.0126(8) 0.0169(9) 0.0062(7) -0.0098(7) -0.0040(7) O2 0.0138(8) 0.0107(8) 0.0219(9) 0.0067(7) -0.0056(7) -0.0019(6) O3 0.0184(8) 0.0128(8) 0.0118(8) 0.0037(7) -0.0076(7) -0.0026(6) O4 0.0235(9) 0.0163(9) 0.0145(8) 0.0078(7) -0.0033(7) 0.0032(7) O5 0.0147(8) 0.0100(8) 0.0164(8) 0.0034(7) -0.0043(7) -0.0015(7) O6 0.0157(8) 0.0137(9) 0.0202(9) 0.0093(7) -0.0015(7) 0.0004(7) N1 0.0100(9) 0.0118(10) 0.0105(9) 0.0044(8) -0.0025(8) -0.0007(7) N2 0.0239(11) 0.0134(10) 0.0167(10) 0.0037(9) -0.0098(9) -0.0033(8) N3 0.0150(10) 0.0183(11) 0.0090(9) 0.0035(8) -0.0038(8) -0.0005(8) N4 0.0126(9) 0.0159(10) 0.0084(9) 0.0030(8) -0.0032(8) -0.0028(8) C1 0.0106(11) 0.0119(12) 0.0175(12) 0.0063(10) 0.0008(10) 0.0008(9) C2 0.0107(11) 0.0114(11) 0.0125(11) 0.0032(9) -0.0012(9) -0.0006(8) C3 0.0234(13) 0.0119(12) 0.0186(12) 0.0035(10) -0.0001(11) -0.0023(9) C4 0.0216(13) 0.0176(13) 0.0176(12) 0.0085(11) -0.0044(10) 0.0004(10) C5 0.0116(11) 0.0152(12) 0.0107(11) 0.0049(9) -0.0018(9) 0.0009(9) C6 0.0136(11) 0.0127(12) 0.0140(12) 0.0059(10) 0.0016(10) 0.0029(9) C7 0.0228(13) 0.0193(13) 0.0161(12) 0.0073(10) -0.0028(11) 0.0043(10) C8 0.0230(13) 0.0269(14) 0.0181(12) 0.0130(11) 0.0022(11) 0.0079(11) C9 0.0140(11) 0.0324(14) 0.0138(12) 0.0114(11) -0.0010(10) 0.0038(10) C10 0.0129(12) 0.0248(13) 0.0112(11) 0.0046(10) -0.0013(9) -0.0012(9) C11 0.0097(11) 0.0213(13) 0.0108(11) 0.0048(10) 0.0006(9) 0.0005(9) C12 0.0113(11) 0.0175(12) 0.0100(11) 0.0024(10) 0.0010(9) -0.0023(9) C13 0.0151(12) 0.0231(13) 0.0129(12) 0.0023(10) -0.0034(10) -0.0030(10) C14 0.0202(13) 0.0184(13) 0.0175(13) 0.0008(10) -0.0012(11) -0.0058(10) C15 0.0247(13) 0.0186(13) 0.0158(12) 0.0061(11) 0.0012(11) -0.0009(10) C16 0.0196(12) 0.0164(12) 0.0131(12) 0.0055(10) -0.0001(10) -0.0006(9) _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 Cd1 N1 2.239(2) . ? Cd1 N3 2.285(2) . ? Cd1 N4 2.315(2) . ? Cd1 O6 2.3638(17) . ? Cd1 O5 2.3895(16) . ? Cd1 O1 2.4214(16) . ? Cd1 O3 2.5341(16) . ? O1 C1 1.188(3) . ? O2 C1 1.251(3) . ? O3 C6 1.189(3) . ? O4 C6 1.217(3) . ? O5 H5A 0.858(9) . ? O5 H5B 0.857(10) . ? O6 H6A 0.836(9) . ? O6 H6B 0.845(10) . ? N1 C5 1.305(3) . ? N1 C2 1.330(3) . ? N2 C3 1.305(3) . ? N2 C4 1.323(3) . ? N3 C11 1.307(3) . ? N3 C7 1.339(3) . ? N4 C12 1.274(3) . ? N4 C16 1.335(3) . ? C1 C2 1.473(3) . ? C2 C3 1.311(3) . ? C3 H3 0.9300 . ? C4 C5 1.309(3) . ? C4 H4 0.9300 . ? C5 C6 1.503(3) . ? C7 C8 1.310(3) . ? C7 H7 0.9300 . ? C8 C9 1.338(4) . ? C8 H8 0.9300 . ? C9 C10 1.377(3) . ? C9 H9 0.9300 . ? C10 C11 1.317(3) . ? C10 H10 0.9300 . ? C11 C12 1.478(3) . ? C12 C13 1.349(3) . ? C13 C14 1.371(3) . ? C13 H13 0.9300 . ? C14 C15 1.295(3) . ? C14 H14 0.9300 . ? C15 C16 1.349(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 Cd1 N3 143.49(7) . . ? N1 Cd1 N4 144.82(7) . . ? N3 Cd1 N4 71.63(7) . . ? N1 Cd1 O6 82.19(6) . . ? N3 Cd1 O6 90.38(6) . . ? N4 Cd1 O6 99.73(7) . . ? N1 Cd1 O5 89.73(6) . . ? N3 Cd1 O5 96.14(6) . . ? N4 Cd1 O5 86.89(7) . . ? O6 Cd1 O5 171.92(5) . . ? N1 Cd1 O1 67.73(6) . . ? N3 Cd1 O1 76.82(7) . . ? N4 Cd1 O1 146.51(6) . . ? O6 Cd1 O1 91.32(6) . . ? O5 Cd1 O1 85.55(6) . . ? N1 Cd1 O3 67.80(6) . . ? N3 Cd1 O3 146.55(6) . . ? N4 Cd1 O3 77.63(6) . . ? O6 Cd1 O3 81.96(6) . . ? O5 Cd1 O3 95.06(5) . . ? O1 Cd1 O3 135.52(6) . . ? C1 O1 Cd1 120.23(15) . . ? C6 O3 Cd1 115.96(14) . . ? Cd1 O5 H5A 109.5(15) . . ? Cd1 O5 H5B 111.8(18) . . ? H5A O5 H5B 113.6(15) . . ? Cd1 O6 H6A 116.2(17) . . ? Cd1 O6 H6B 109.8(18) . . ? H6A O6 H6B 118.9(17) . . ? C5 N1 C2 120.5(2) . . ? C5 N1 Cd1 120.46(14) . . ? C2 N1 Cd1 119.04(14) . . ? C3 N2 C4 118.5(2) . . ? C11 N3 C7 120.9(2) . . ? C11 N3 Cd1 115.15(15) . . ? C7 N3 Cd1 123.95(16) . . ? C12 N4 C16 118.0(2) . . ? C12 N4 Cd1 116.42(15) . . ? C16 N4 Cd1 125.04(16) . . ? O1 C1 O2 126.7(2) . . ? O1 C1 C2 114.5(2) . . ? O2 C1 C2 118.8(2) . . ? C3 C2 N1 120.4(2) . . ? C3 C2 C1 121.2(2) . . ? N1 C2 C1 118.5(2) . . ? N2 C3 C2 119.9(2) . . ? N2 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 N2 122.8(2) . . ? C5 C4 H4 118.6 . . ? N2 C4 H4 118.6 . . ? N1 C5 C4 117.8(2) . . ? N1 C5 C6 119.3(2) . . ? C4 C5 C6 122.8(2) . . ? O3 C6 O4 125.5(2) . . ? O3 C6 C5 116.46(19) . . ? O4 C6 C5 118.0(2) . . ? C8 C7 N3 123.3(2) . . ? C8 C7 H7 118.4 . . ? N3 C7 H7 118.4 . . ? C7 C8 C9 115.9(2) . . ? C7 C8 H8 122.0 . . ? C9 C8 H8 122.0 . . ? C8 C9 C10 121.3(2) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 119.9(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? N3 C11 C10 118.7(2) . . ? N3 C11 C12 119.3(2) . . ? C10 C11 C12 122.0(2) . . ? N4 C12 C13 118.5(2) . . ? N4 C12 C11 116.6(2) . . ? C13 C12 C11 124.8(2) . . ? C12 C13 C14 122.6(2) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C15 C14 C13 119.0(2) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 115.7(2) . . ? C14 C15 H15 122.1 . . ? C16 C15 H15 122.1 . . ? N4 C16 C15 126.0(2) . . ? N4 C16 H16 117.0 . . ? C15 C16 H16 117.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cd1 O1 C1 0.30(16) . . . . ? N3 Cd1 O1 C1 171.39(18) . . . . ? N4 Cd1 O1 C1 -168.74(16) . . . . ? O6 Cd1 O1 C1 81.31(17) . . . . ? O5 Cd1 O1 C1 -91.23(17) . . . . ? O3 Cd1 O1 C1 1.5(2) . . . . ? N1 Cd1 O3 C6 0.09(15) . . . . ? N3 Cd1 O3 C6 -163.09(15) . . . . ? N4 Cd1 O3 C6 173.42(16) . . . . ? O6 Cd1 O3 C6 -84.72(16) . . . . ? O5 Cd1 O3 C6 87.72(16) . . . . ? O1 Cd1 O3 C6 -1.07(19) . . . . ? N3 Cd1 N1 C5 164.78(15) . . . . ? N4 Cd1 N1 C5 -11.0(2) . . . . ? O6 Cd1 N1 C5 84.80(16) . . . . ? O5 Cd1 N1 C5 -95.24(16) . . . . ? O1 Cd1 N1 C5 179.46(17) . . . . ? O3 Cd1 N1 C5 0.34(15) . . . . ? N3 Cd1 N1 C2 -16.1(2) . . . . ? N4 Cd1 N1 C2 168.07(13) . . . . ? O6 Cd1 N1 C2 -96.10(15) . . . . ? O5 Cd1 N1 C2 83.86(15) . . . . ? O1 Cd1 N1 C2 -1.44(14) . . . . ? O3 Cd1 N1 C2 179.43(16) . . . . ? N1 Cd1 N3 C11 -173.14(13) . . . . ? N4 Cd1 N3 C11 4.32(15) . . . . ? O6 Cd1 N3 C11 -95.81(16) . . . . ? O5 Cd1 N3 C11 88.98(16) . . . . ? O1 Cd1 N3 C11 172.93(16) . . . . ? O3 Cd1 N3 C11 -19.9(2) . . . . ? N1 Cd1 N3 C7 6.4(2) . . . . ? N4 Cd1 N3 C7 -176.14(19) . . . . ? O6 Cd1 N3 C7 83.73(19) . . . . ? O5 Cd1 N3 C7 -91.48(19) . . . . ? O1 Cd1 N3 C7 -7.53(18) . . . . ? O3 Cd1 N3 C7 159.64(16) . . . . ? N1 Cd1 N4 C12 169.18(14) . . . . ? N3 Cd1 N4 C12 -8.20(15) . . . . ? O6 Cd1 N4 C12 78.94(16) . . . . ? O5 Cd1 N4 C12 -105.72(16) . . . . ? O1 Cd1 N4 C12 -28.6(2) . . . . ? O3 Cd1 N4 C12 158.41(16) . . . . ? N1 Cd1 N4 C16 -2.5(2) . . . . ? N3 Cd1 N4 C16 -179.86(19) . . . . ? O6 Cd1 N4 C16 -92.71(18) . . . . ? O5 Cd1 N4 C16 82.63(18) . . . . ? O1 Cd1 N4 C16 159.74(15) . . . . ? O3 Cd1 N4 C16 -13.24(17) . . . . ? Cd1 O1 C1 O2 179.48(16) . . . . ? Cd1 O1 C1 C2 0.7(3) . . . . ? C5 N1 C2 C3 1.6(3) . . . . ? Cd1 N1 C2 C3 -177.55(17) . . . . ? C5 N1 C2 C1 -178.5(2) . . . . ? Cd1 N1 C2 C1 2.4(2) . . . . ? O1 C1 C2 C3 177.9(2) . . . . ? O2 C1 C2 C3 -0.9(3) . . . . ? O1 C1 C2 N1 -2.1(3) . . . . ? O2 C1 C2 N1 179.09(18) . . . . ? C4 N2 C3 C2 1.8(4) . . . . ? N1 C2 C3 N2 -2.8(3) . . . . ? C1 C2 C3 N2 177.2(2) . . . . ? C3 N2 C4 C5 0.5(4) . . . . ? C2 N1 C5 C4 0.7(3) . . . . ? Cd1 N1 C5 C4 179.77(16) . . . . ? C2 N1 C5 C6 -179.78(18) . . . . ? Cd1 N1 C5 C6 -0.7(3) . . . . ? N2 C4 C5 N1 -1.7(4) . . . . ? N2 C4 C5 C6 178.8(2) . . . . ? Cd1 O3 C6 O4 178.79(17) . . . . ? Cd1 O3 C6 C5 -0.4(2) . . . . ? N1 C5 C6 O3 0.8(3) . . . . ? C4 C5 C6 O3 -179.7(2) . . . . ? N1 C5 C6 O4 -178.5(2) . . . . ? C4 C5 C6 O4 1.0(3) . . . . ? C11 N3 C7 C8 0.0(4) . . . . ? Cd1 N3 C7 C8 -179.52(18) . . . . ? N3 C7 C8 C9 -0.8(4) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C7 N3 C11 C10 0.8(3) . . . . ? Cd1 N3 C11 C10 -179.60(16) . . . . ? C7 N3 C11 C12 179.7(2) . . . . ? Cd1 N3 C11 C12 -0.8(3) . . . . ? C9 C10 C11 N3 -0.9(3) . . . . ? C9 C10 C11 C12 -179.7(2) . . . . ? C16 N4 C12 C13 1.7(3) . . . . ? Cd1 N4 C12 C13 -170.59(16) . . . . ? C16 N4 C12 C11 -177.13(19) . . . . ? Cd1 N4 C12 C11 10.6(2) . . . . ? N3 C11 C12 N4 -6.8(3) . . . . ? C10 C11 C12 N4 172.0(2) . . . . ? N3 C11 C12 C13 174.5(2) . . . . ? C10 C11 C12 C13 -6.7(4) . . . . ? N4 C12 C13 C14 0.1(3) . . . . ? C11 C12 C13 C14 178.8(2) . . . . ? C12 C13 C14 C15 -1.4(4) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C12 N4 C16 C15 -2.4(3) . . . . ? Cd1 N4 C16 C15 169.18(18) . . . . ? C14 C15 C16 N4 1.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.578 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.073