Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 # SUBMISSION DETAILS _publ_contact_author_name 'Dr. Zhen-Feng Chen' _publ_contact_author_address ; The Key Laboratory of Medicinal Chemical Resources and Molecular Engineering (Ministry of Education) School of Chemistry and Chemical Guangxi Normal University Guilin 541004 China ; _publ_contact_author_email chenzfubc@yahoo.com _publ_contact_author_fax '86 773 5812383' _publ_contact_author_phone '86 773 5837207' #========================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Coordination Polymers Constructed by Linking Metal Ions with Azodibenzoate Anions ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Zhen-Feng Chen.' ? ; The Key Laboratory of Medicinal Chemical Resources and Molecular Engineering (Ministry of Education) School of Chemistry and Chemical Guangxi Normal University Guilin 541004 China ; 'Zhi-Li Zhang.' ? ; The Key Laboratory of Medicinal Chemical Resources and Molecular Engineering (Ministry of Education) School of Chemistry and Chemical Guangxi Normal University Guilin 541004 China ; 'Yu-Hui Tan.' ? ; The Key Laboratory of Medicinal Chemical Resources and Molecular Engineering (Ministry of Education) School of Chemistry and Chemical Guangxi Normal University Guilin 541004 China ; 'Yun-Zhi Tang.' ? ; The Key Laboratory of Medicinal Chemical Resources and Molecular Engineering (Ministry of Education) School of Chemistry and Chemical Guangxi Normal University Guilin 541004 China ; ; Hoong-Kun Fun ; ? ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; 'Zhong-Yuan Zhou.' ? ; Department of Applied Biology and Chemical Technology The Hong Kong Polytechnic University Hung Hom, Kownloon Hong Kong China ; 'Brendan F. Abrahams' ? ; School of Chemistry University of Melbourne Parkville, Victoria, 3010 Australia ; 'Hong Liang.' ? ; The Key Laboratory of Medicinal Chemical Resources and Molecular Engineering (Ministry of Education) School of Chemistry and Chemical Guangxi Normal University Guilin 541004 China ; #========================================================================== data_shelxl _database_code_depnum_ccdc_archive 'CCDC 651798' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H16 N4 O4 Pb' _chemical_formula_weight 655.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8207(13) _cell_length_b 11.2083(10) _cell_length_c 11.8496(11) _cell_angle_alpha 62.435(10) _cell_angle_beta 77.407(13) _cell_angle_gamma 71.735(12) _cell_volume 1093.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.991 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 7.755 _exptl_absorpt_correction_T_min 0.1972 _exptl_absorpt_correction_T_max 0.3061 _exptl_absorpt_correction_type 'multi scans' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12197 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4912 _reflns_number_gt 4655 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0278P)^2^+2.6784P] 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 4912 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0665 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Pb1 Pb 0.190602(16) 0.094949(16) 0.342237(14) 0.02597(6) Uani 1 1 d . . . O1 O 0.2976(3) -0.0796(3) 0.5370(3) 0.0355(7) Uani 1 1 d . . . O2 O 0.0813(3) 0.0289(3) 0.5892(3) 0.0330(7) Uani 1 1 d . . . O3 O 0.2733(3) 0.2399(3) 0.3815(3) 0.0320(7) Uani 1 1 d . . . O4 O 0.0665(4) 0.3661(4) 0.2965(3) 0.0443(9) Uani 1 1 d . . . N1 N 0.4561(4) 0.0257(4) 0.2619(3) 0.0257(7) Uani 1 1 d . . . N2 N 0.2715(4) 0.2469(4) 0.0971(3) 0.0286(8) Uani 1 1 d . . . N3 N 0.4930(5) -0.4594(4) 0.9429(4) 0.0343(9) Uani 1 1 d . . . N4 N 0.4472(5) 0.5487(4) 0.4986(4) 0.0455(11) Uani 1 1 d . . . C1 C 0.5493(5) -0.0785(5) 0.3418(4) 0.0317(9) Uani 1 1 d . . . H1 H 0.5200 -0.1155 0.4306 0.038 Uiso 1 1 calc R . . C2 C 0.6872(5) -0.1355(5) 0.3011(5) 0.0349(10) Uani 1 1 d . . . H2 H 0.7499 -0.2100 0.3612 0.042 Uiso 1 1 calc R . . C3 C 0.7312(5) -0.0835(5) 0.1744(5) 0.0360(10) Uani 1 1 d . . . H3 H 0.8249 -0.1219 0.1452 0.043 Uiso 1 1 calc R . . C4 C 0.6374(5) 0.0274(5) 0.0866(4) 0.0293(9) Uani 1 1 d . . . C5 C 0.5002(5) 0.0804(4) 0.1349(4) 0.0245(8) Uani 1 1 d . . . C6 C 0.1808(5) 0.3536(5) 0.0171(4) 0.0327(10) Uani 1 1 d . . . H6 H 0.0887 0.3884 0.0515 0.039 Uiso 1 1 calc R . . C7 C 0.2140(6) 0.4170(5) -0.1148(5) 0.0381(11) Uani 1 1 d . . . H7 H 0.1463 0.4932 -0.1686 0.046 Uiso 1 1 calc R . . C8 C 0.3455(6) 0.3673(5) -0.1643(4) 0.0390(11) Uani 1 1 d . . . H8 H 0.3706 0.4090 -0.2538 0.047 Uiso 1 1 calc R . . C9 C 0.4448(5) 0.2541(5) -0.0836(4) 0.0299(9) Uani 1 1 d . . . C10 C 0.4027(5) 0.1962(4) 0.0485(4) 0.0247(8) Uani 1 1 d . . . C11 C 0.6762(5) 0.0887(5) -0.0487(5) 0.0365(10) Uani 1 1 d . . . H11 H 0.7685 0.0522 -0.0817 0.044 Uiso 1 1 calc R . . C12 C 0.5851(6) 0.1965(5) -0.1295(4) 0.0399(11) Uani 1 1 d . . . H12 H 0.6141 0.2351 -0.2184 0.048 Uiso 1 1 calc R . . C13 C 0.1957(5) -0.0645(4) 0.6183(4) 0.0261(8) Uani 1 1 d . . . C14 C 0.2136(5) -0.1651(4) 0.7563(4) 0.0254(8) Uani 1 1 d . . . C15 C 0.3411(5) -0.2658(4) 0.7900(4) 0.0264(8) Uani 1 1 d . . . H15 H 0.4169 -0.2720 0.7261 0.032 Uiso 1 1 calc R . . C16 C 0.3580(5) -0.3583(4) 0.9178(4) 0.0296(9) Uani 1 1 d . . . C17 C 0.2467(6) -0.3511(5) 1.0117(4) 0.0392(11) Uani 1 1 d . . . H17 H 0.2575 -0.4151 1.0986 0.047 Uiso 1 1 calc R . . C18 C 0.1209(6) -0.2503(6) 0.9770(4) 0.0402(11) Uani 1 1 d . . . H18 H 0.0447 -0.2446 1.0408 0.048 Uiso 1 1 calc R . . C19 C 0.1034(5) -0.1566(5) 0.8503(4) 0.0326(10) Uani 1 1 d . . . H19 H 0.0162 -0.0869 0.8279 0.039 Uiso 1 1 calc R . . C20 C 0.1733(5) 0.3519(5) 0.3459(4) 0.0310(9) Uani 1 1 d . . . C21 C 0.1886(5) 0.4670(4) 0.3708(4) 0.0321(10) Uani 1 1 d . . . C22 C 0.3131(5) 0.4527(4) 0.4173(4) 0.0318(10) Uani 1 1 d . . . H22 H 0.3915 0.3739 0.4273 0.038 Uiso 1 1 calc R . . C23 C 0.3232(6) 0.5544(5) 0.4495(5) 0.0424(13) Uani 1 1 d . . . C24 C 0.2085(7) 0.6690(6) 0.4364(6) 0.0526(16) Uani 1 1 d . . . H24 H 0.2141 0.7363 0.4615 0.063 Uiso 1 1 calc R . . C25 C 0.0868(7) 0.6846(5) 0.3868(6) 0.0547(17) Uani 1 1 d . . . H25 H 0.0095 0.7644 0.3754 0.066 Uiso 1 1 calc R . . C26 C 0.0751(6) 0.5847(5) 0.3529(5) 0.0432(12) Uani 1 1 d . . . H26 H -0.0092 0.5966 0.3180 0.052 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 Pb1 0.02548(9) 0.03085(10) 0.01989(8) -0.00635(6) -0.00389(6) -0.01045(6) O1 0.0338(17) 0.0388(18) 0.0190(14) -0.0039(13) 0.0006(13) -0.0046(14) O2 0.0267(16) 0.0348(17) 0.0330(17) -0.0121(14) -0.0084(13) -0.0015(13) O3 0.0318(16) 0.0267(16) 0.0382(17) -0.0126(14) -0.0131(14) -0.0033(13) O4 0.0331(18) 0.058(2) 0.0370(19) -0.0215(17) -0.0132(15) 0.0038(16) N1 0.0296(18) 0.0263(18) 0.0190(16) -0.0073(14) -0.0038(14) -0.0064(14) N2 0.0296(19) 0.0283(19) 0.0253(18) -0.0081(15) -0.0062(15) -0.0064(15) N3 0.047(2) 0.0269(19) 0.0226(18) -0.0018(14) -0.0087(16) -0.0110(17) N4 0.065(3) 0.039(2) 0.041(2) -0.023(2) 0.011(2) -0.025(2) C1 0.033(2) 0.030(2) 0.024(2) -0.0037(18) -0.0042(18) -0.0077(18) C2 0.033(2) 0.028(2) 0.035(2) -0.0070(19) -0.0079(19) -0.0025(18) C3 0.028(2) 0.040(3) 0.041(3) -0.022(2) 0.001(2) -0.0041(19) C4 0.032(2) 0.030(2) 0.030(2) -0.0155(18) 0.0036(18) -0.0126(18) C5 0.030(2) 0.026(2) 0.0215(19) -0.0107(16) -0.0031(16) -0.0107(17) C6 0.033(2) 0.032(2) 0.027(2) -0.0055(18) -0.0063(18) -0.0087(19) C7 0.047(3) 0.030(2) 0.030(2) -0.0019(19) -0.016(2) -0.009(2) C8 0.053(3) 0.038(3) 0.018(2) -0.0015(19) -0.009(2) -0.014(2) C9 0.042(3) 0.029(2) 0.0206(19) -0.0079(17) -0.0003(18) -0.0173(19) C10 0.031(2) 0.028(2) 0.0194(18) -0.0098(16) 0.0000(16) -0.0141(17) C11 0.036(2) 0.043(3) 0.035(2) -0.022(2) 0.008(2) -0.013(2) C12 0.050(3) 0.048(3) 0.021(2) -0.013(2) 0.007(2) -0.021(2) C13 0.029(2) 0.029(2) 0.0213(19) -0.0091(17) -0.0049(16) -0.0103(17) C14 0.031(2) 0.028(2) 0.0206(19) -0.0100(16) -0.0011(16) -0.0129(17) C15 0.035(2) 0.025(2) 0.0183(18) -0.0072(16) 0.0002(16) -0.0118(17) C16 0.042(3) 0.024(2) 0.022(2) -0.0065(16) -0.0038(18) -0.0104(18) C17 0.055(3) 0.044(3) 0.019(2) -0.0064(19) -0.001(2) -0.025(2) C18 0.039(3) 0.062(3) 0.023(2) -0.019(2) 0.0081(19) -0.022(2) C19 0.029(2) 0.043(3) 0.030(2) -0.016(2) -0.0011(18) -0.013(2) C20 0.030(2) 0.035(2) 0.0190(19) -0.0069(17) 0.0005(17) -0.0041(18) C21 0.039(2) 0.024(2) 0.021(2) -0.0053(17) 0.0058(18) -0.0041(18) C22 0.047(3) 0.019(2) 0.024(2) -0.0064(16) 0.0050(19) -0.0111(18) C23 0.067(4) 0.029(2) 0.029(2) -0.0133(19) 0.020(2) -0.023(2) C24 0.071(4) 0.033(3) 0.051(3) -0.026(2) 0.032(3) -0.022(3) C25 0.062(4) 0.024(2) 0.052(3) -0.012(2) 0.028(3) -0.005(2) C26 0.044(3) 0.035(3) 0.031(2) -0.008(2) 0.007(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 Pb1 O3 2.282(3) . ? Pb1 O1 2.418(3) . ? Pb1 N1 2.577(4) . ? Pb1 N2 2.689(4) . ? Pb1 O2 2.718(3) . ? Pb1 O4 2.731(4) . ? Pb1 C20 2.851(5) . ? Pb1 C13 2.916(4) . ? O1 C13 1.258(5) . ? O2 C13 1.254(5) . ? O3 C20 1.279(5) . ? O4 C20 1.243(6) . ? N1 C1 1.335(6) . ? N1 C5 1.362(5) . ? N2 C6 1.332(6) . ? N2 C10 1.355(6) . ? N3 N3 1.242(7) 2_647 ? N3 C16 1.431(6) . ? N4 N4 1.240(9) 2_666 ? N4 C23 1.432(8) . ? C1 C2 1.389(7) . ? C1 H1 0.9500 . ? C2 C3 1.359(7) . ? C2 H2 0.9500 . ? C3 C4 1.407(7) . ? C3 H3 0.9500 . ? C4 C5 1.405(6) . ? C4 C11 1.437(6) . ? C5 C10 1.438(6) . ? C6 C7 1.396(6) . ? C6 H6 0.9500 . ? C7 C8 1.358(8) . ? C7 H7 0.9500 . ? C8 C9 1.408(7) . ? C8 H8 0.9500 . ? C9 C10 1.410(6) . ? C9 C12 1.433(7) . ? C11 C12 1.342(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.507(6) . ? C14 C15 1.385(6) . ? C14 C19 1.389(6) . ? C15 C16 1.395(6) . ? C15 H15 0.9500 . ? C16 C17 1.391(7) . ? C17 C18 1.374(8) . ? C17 H17 0.9500 . ? C18 C19 1.388(7) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.506(7) . ? C21 C22 1.384(7) . ? C21 C26 1.396(6) . ? C22 C23 1.395(6) . ? C22 H22 0.9500 . ? C23 C24 1.389(8) . ? C24 C25 1.373(10) . ? C24 H24 0.9500 . ? C25 C26 1.394(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 Pb1 O1 83.62(11) . . ? O3 Pb1 N1 82.61(11) . . ? O1 Pb1 N1 77.65(11) . . ? O3 Pb1 N2 83.94(11) . . ? O1 Pb1 N2 139.49(11) . . ? N1 Pb1 N2 62.59(11) . . ? O3 Pb1 O2 80.71(11) . . ? O1 Pb1 O2 50.52(10) . . ? N1 Pb1 O2 126.77(10) . . ? N2 Pb1 O2 160.34(11) . . ? O3 Pb1 O4 51.54(11) . . ? O1 Pb1 O4 124.40(11) . . ? N1 Pb1 O4 119.28(11) . . ? N2 Pb1 O4 73.77(11) . . ? O2 Pb1 O4 87.04(10) . . ? O3 Pb1 C20 25.94(12) . . ? O1 Pb1 C20 104.28(12) . . ? N1 Pb1 C20 102.18(12) . . ? N2 Pb1 C20 78.36(11) . . ? O2 Pb1 C20 82.48(11) . . ? O4 Pb1 C20 25.61(11) . . ? O3 Pb1 C13 82.33(11) . . ? O1 Pb1 C13 25.14(11) . . ? N1 Pb1 C13 102.36(11) . . ? N2 Pb1 C13 160.89(12) . . ? O2 Pb1 C13 25.41(11) . . ? O4 Pb1 C13 107.24(11) . . ? C20 Pb1 C13 94.61(12) . . ? C13 O1 Pb1 100.1(3) . . ? C13 O2 Pb1 86.2(2) . . ? C20 O3 Pb1 102.7(3) . . ? C20 O4 Pb1 82.6(3) . . ? C1 N1 C5 118.1(4) . . ? C1 N1 Pb1 120.3(3) . . ? C5 N1 Pb1 121.0(3) . . ? C6 N2 C10 118.5(4) . . ? C6 N2 Pb1 123.0(3) . . ? C10 N2 Pb1 117.3(3) . . ? N3 N3 C16 115.1(5) 2_647 . ? N4 N4 C23 115.4(5) 2_666 . ? N1 C1 C2 123.2(4) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 117.8(4) . . ? C5 C4 C11 119.1(4) . . ? C3 C4 C11 123.1(4) . . ? N1 C5 C4 122.0(4) . . ? N1 C5 C10 118.6(4) . . ? C4 C5 C10 119.4(4) . . ? N2 C6 C7 123.5(5) . . ? N2 C6 H6 118.3 . . ? C7 C6 H6 118.3 . . ? C8 C7 C6 118.4(4) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C9 120.3(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 117.7(4) . . ? C8 C9 C12 123.1(4) . . ? C10 C9 C12 119.2(4) . . ? N2 C10 C9 121.6(4) . . ? N2 C10 C5 118.5(4) . . ? C9 C10 C5 119.8(4) . . ? C12 C11 C4 121.5(4) . . ? C12 C11 H11 119.2 . . ? C4 C11 H11 119.2 . . ? C11 C12 C9 120.9(4) . . ? C11 C12 H12 119.5 . . ? C9 C12 H12 119.5 . . ? O2 C13 O1 123.0(4) . . ? O2 C13 C14 119.4(4) . . ? O1 C13 C14 117.5(4) . . ? O2 C13 Pb1 68.4(2) . . ? O1 C13 Pb1 54.7(2) . . ? C14 C13 Pb1 171.1(3) . . ? C15 C14 C19 119.7(4) . . ? C15 C14 C13 119.9(4) . . ? C19 C14 C13 120.4(4) . . ? C14 C15 C16 119.9(4) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 120.4(4) . . ? C17 C16 N3 123.9(4) . . ? C15 C16 N3 115.7(4) . . ? C18 C17 C16 119.1(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 121.0(4) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C14 119.9(4) . . ? C18 C19 H19 120.1 . . ? C14 C19 H19 120.1 . . ? O4 C20 O3 123.0(5) . . ? O4 C20 C21 120.7(4) . . ? O3 C20 C21 116.3(4) . . ? O4 C20 Pb1 71.8(3) . . ? O3 C20 Pb1 51.3(2) . . ? C21 C20 Pb1 166.8(3) . . ? C22 C21 C26 120.1(5) . . ? C22 C21 C20 119.6(4) . . ? C26 C21 C20 120.2(5) . . ? C21 C22 C23 119.7(5) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 120.3(6) . . ? C24 C23 N4 115.8(5) . . ? C22 C23 N4 123.8(5) . . ? C25 C24 C23 119.6(5) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.9(5) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 119.3(6) . . ? C25 C26 H26 120.4 . . ? C21 C26 H26 120.4 . . ? 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 O3 Pb1 O1 C13 85.5(3) . . . . ? N1 Pb1 O1 C13 169.3(3) . . . . ? N2 Pb1 O1 C13 158.4(2) . . . . ? O2 Pb1 O1 C13 2.3(2) . . . . ? O4 Pb1 O1 C13 52.1(3) . . . . ? C20 Pb1 O1 C13 69.7(3) . . . . ? O3 Pb1 O2 C13 -91.7(3) . . . . ? O1 Pb1 O2 C13 -2.3(2) . . . . ? N1 Pb1 O2 C13 -18.2(3) . . . . ? N2 Pb1 O2 C13 -130.8(3) . . . . ? O4 Pb1 O2 C13 -143.2(3) . . . . ? C20 Pb1 O2 C13 -117.8(3) . . . . ? O1 Pb1 O3 C20 -142.8(3) . . . . ? N1 Pb1 O3 C20 138.8(3) . . . . ? N2 Pb1 O3 C20 75.8(3) . . . . ? O2 Pb1 O3 C20 -91.9(3) . . . . ? O4 Pb1 O3 C20 1.7(2) . . . . ? C13 Pb1 O3 C20 -117.5(3) . . . . ? O3 Pb1 O4 C20 -1.7(2) . . . . ? O1 Pb1 O4 C20 42.5(3) . . . . ? N1 Pb1 O4 C20 -52.4(3) . . . . ? N2 Pb1 O4 C20 -97.0(3) . . . . ? O2 Pb1 O4 C20 78.7(3) . . . . ? C13 Pb1 O4 C20 63.1(3) . . . . ? O3 Pb1 N1 C1 90.5(3) . . . . ? O1 Pb1 N1 C1 5.5(3) . . . . ? N2 Pb1 N1 C1 177.5(4) . . . . ? O2 Pb1 N1 C1 18.0(4) . . . . ? O4 Pb1 N1 C1 128.1(3) . . . . ? C20 Pb1 N1 C1 107.6(3) . . . . ? C13 Pb1 N1 C1 10.1(3) . . . . ? O3 Pb1 N1 C5 -98.7(3) . . . . ? O1 Pb1 N1 C5 176.2(3) . . . . ? N2 Pb1 N1 C5 -11.8(3) . . . . ? O2 Pb1 N1 C5 -171.3(3) . . . . ? O4 Pb1 N1 C5 -61.1(3) . . . . ? C20 Pb1 N1 C5 -81.6(3) . . . . ? C13 Pb1 N1 C5 -179.2(3) . . . . ? O3 Pb1 N2 C6 -95.8(4) . . . . ? O1 Pb1 N2 C6 -168.6(3) . . . . ? N1 Pb1 N2 C6 179.4(4) . . . . ? O2 Pb1 N2 C6 -57.1(5) . . . . ? O4 Pb1 N2 C6 -44.2(3) . . . . ? C20 Pb1 N2 C6 -70.2(4) . . . . ? C13 Pb1 N2 C6 -140.1(4) . . . . ? O3 Pb1 N2 C10 96.5(3) . . . . ? O1 Pb1 N2 C10 23.7(4) . . . . ? N1 Pb1 N2 C10 11.7(3) . . . . ? O2 Pb1 N2 C10 135.2(3) . . . . ? O4 Pb1 N2 C10 148.1(3) . . . . ? C20 Pb1 N2 C10 122.1(3) . . . . ? C13 Pb1 N2 C10 52.2(5) . . . . ? C5 N1 C1 C2 -1.6(7) . . . . ? Pb1 N1 C1 C2 169.4(4) . . . . ? N1 C1 C2 C3 0.3(7) . . . . ? C1 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C2 C3 C4 C11 179.6(4) . . . . ? C1 N1 C5 C4 2.2(6) . . . . ? Pb1 N1 C5 C4 -168.8(3) . . . . ? C1 N1 C5 C10 -177.6(4) . . . . ? Pb1 N1 C5 C10 11.4(5) . . . . ? C3 C4 C5 N1 -1.5(6) . . . . ? C11 C4 C5 N1 179.1(4) . . . . ? C3 C4 C5 C10 178.4(4) . . . . ? C11 C4 C5 C10 -1.1(6) . . . . ? C10 N2 C6 C7 -0.4(7) . . . . ? Pb1 N2 C6 C7 -167.9(4) . . . . ? N2 C6 C7 C8 0.1(8) . . . . ? C6 C7 C8 C9 0.2(7) . . . . ? C7 C8 C9 C10 -0.3(7) . . . . ? C7 C8 C9 C12 180.0(5) . . . . ? C6 N2 C10 C9 0.2(6) . . . . ? Pb1 N2 C10 C9 168.5(3) . . . . ? C6 N2 C10 C5 -179.6(4) . . . . ? Pb1 N2 C10 C5 -11.4(5) . . . . ? C8 C9 C10 N2 0.1(6) . . . . ? C12 C9 C10 N2 179.8(4) . . . . ? C8 C9 C10 C5 180.0(4) . . . . ? C12 C9 C10 C5 -0.3(6) . . . . ? N1 C5 C10 N2 0.6(6) . . . . ? C4 C5 C10 N2 -179.3(4) . . . . ? N1 C5 C10 C9 -179.3(4) . . . . ? C4 C5 C10 C9 0.9(6) . . . . ? C5 C4 C11 C12 0.9(7) . . . . ? C3 C4 C11 C12 -178.6(5) . . . . ? C4 C11 C12 C9 -0.3(8) . . . . ? C8 C9 C12 C11 179.8(5) . . . . ? C10 C9 C12 C11 0.1(7) . . . . ? Pb1 O2 C13 O1 4.1(4) . . . . ? Pb1 O2 C13 C14 -175.3(3) . . . . ? Pb1 O1 C13 O2 -4.6(5) . . . . ? Pb1 O1 C13 C14 174.8(3) . . . . ? O3 Pb1 C13 O2 84.5(2) . . . . ? O1 Pb1 C13 O2 175.8(4) . . . . ? N1 Pb1 C13 O2 165.1(2) . . . . ? N2 Pb1 C13 O2 128.9(4) . . . . ? O4 Pb1 C13 O2 38.8(3) . . . . ? C20 Pb1 C13 O2 61.6(3) . . . . ? O3 Pb1 C13 O1 -91.3(3) . . . . ? N1 Pb1 C13 O1 -10.7(3) . . . . ? N2 Pb1 C13 O1 -46.9(5) . . . . ? O2 Pb1 C13 O1 -175.8(4) . . . . ? O4 Pb1 C13 O1 -137.0(3) . . . . ? C20 Pb1 C13 O1 -114.2(3) . . . . ? O3 Pb1 C13 C14 -122.8(18) . . . . ? O1 Pb1 C13 C14 -31.4(17) . . . . ? N1 Pb1 C13 C14 -42.1(18) . . . . ? N2 Pb1 C13 C14 -78.3(19) . . . . ? O2 Pb1 C13 C14 153(2) . . . . ? O4 Pb1 C13 C14 -168.4(18) . . . . ? C20 Pb1 C13 C14 -145.7(18) . . . . ? O2 C13 C14 C15 -178.0(4) . . . . ? O1 C13 C14 C15 2.6(6) . . . . ? Pb1 C13 C14 C15 31(2) . . . . ? O2 C13 C14 C19 1.4(6) . . . . ? O1 C13 C14 C19 -178.0(4) . . . . ? Pb1 C13 C14 C19 -149.3(17) . . . . ? C19 C14 C15 C16 0.2(6) . . . . ? C13 C14 C15 C16 179.6(4) . . . . ? C14 C15 C16 C17 0.8(7) . . . . ? C14 C15 C16 N3 179.5(4) . . . . ? N3 N3 C16 C17 -1.7(8) 2_647 . . . ? N3 N3 C16 C15 179.7(5) 2_647 . . . ? C15 C16 C17 C18 -1.1(7) . . . . ? N3 C16 C17 C18 -179.6(4) . . . . ? C16 C17 C18 C19 0.3(8) . . . . ? C17 C18 C19 C14 0.7(7) . . . . ? C15 C14 C19 C18 -0.9(7) . . . . ? C13 C14 C19 C18 179.7(4) . . . . ? Pb1 O4 C20 O3 2.9(4) . . . . ? Pb1 O4 C20 C21 -175.1(4) . . . . ? Pb1 O3 C20 O4 -3.5(5) . . . . ? Pb1 O3 C20 C21 174.6(3) . . . . ? O3 Pb1 C20 O4 176.9(4) . . . . ? O1 Pb1 C20 O4 -144.8(3) . . . . ? N1 Pb1 C20 O4 135.0(3) . . . . ? N2 Pb1 C20 O4 76.7(3) . . . . ? O2 Pb1 C20 O4 -98.9(3) . . . . ? C13 Pb1 C20 O4 -121.3(3) . . . . ? O1 Pb1 C20 O3 38.3(3) . . . . ? N1 Pb1 C20 O3 -41.9(3) . . . . ? N2 Pb1 C20 O3 -100.2(3) . . . . ? O2 Pb1 C20 O3 84.2(3) . . . . ? O4 Pb1 C20 O3 -176.9(4) . . . . ? C13 Pb1 C20 O3 61.8(3) . . . . ? O3 Pb1 C20 C21 -21.7(12) . . . . ? O1 Pb1 C20 C21 16.6(13) . . . . ? N1 Pb1 C20 C21 -63.6(13) . . . . ? N2 Pb1 C20 C21 -121.9(13) . . . . ? O2 Pb1 C20 C21 62.5(13) . . . . ? O4 Pb1 C20 C21 161.4(14) . . . . ? C13 Pb1 C20 C21 40.1(13) . . . . ? O4 C20 C21 C22 -175.4(4) . . . . ? O3 C20 C21 C22 6.5(6) . . . . ? Pb1 C20 C21 C22 25.2(15) . . . . ? O4 C20 C21 C26 7.7(6) . . . . ? O3 C20 C21 C26 -170.5(4) . . . . ? Pb1 C20 C21 C26 -151.7(11) . . . . ? C26 C21 C22 C23 1.8(6) . . . . ? C20 C21 C22 C23 -175.2(4) . . . . ? C21 C22 C23 C24 0.7(7) . . . . ? C21 C22 C23 N4 179.8(4) . . . . ? N4 N4 C23 C24 -175.1(5) 2_666 . . . ? N4 N4 C23 C22 5.7(8) 2_666 . . . ? C22 C23 C24 C25 -2.5(7) . . . . ? N4 C23 C24 C25 178.3(5) . . . . ? C23 C24 C25 C26 1.9(8) . . . . ? C24 C25 C26 C21 0.5(8) . . . . ? C22 C21 C26 C25 -2.3(7) . . . . ? C20 C21 C26 C25 174.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.247 _refine_diff_density_min -1.059 _refine_diff_density_rms 0.118 # Attachment 'Compound 2.CIF' #========================================================================== data_zz7 _database_code_depnum_ccdc_archive 'CCDC 651799' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H38 Cu2 N2 O5 P2' _chemical_formula_weight 935.84 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' P P 0.1023 0.0942 '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 15.152(3) _cell_length_b 12.764(2) _cell_length_c 22.213(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.324(5) _cell_angle_gamma 90.00 _cell_volume 4260.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3206 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 1.125 _exptl_absorpt_correction_type 'multi scans' _exptl_absorpt_correction_T_min 0.668 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SAINT ver 6.45 2003; Bruker 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 28808 _diffrn_reflns_av_R_equivalents 0.1542 _diffrn_reflns_av_sigmaI/netI 0.3186 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.58 _reflns_number_total 9824 _reflns_number_gt 2446 _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^)+(0.0021P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9824 _refine_ls_number_parameters 550 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2322 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _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 Cu1 Cu 0.12681(3) 0.38980(4) 0.31885(2) 0.05548(15) Uani 1 1 d . . . Cu2 Cu 0.29583(3) 0.35957(4) 0.39780(2) 0.05967(16) Uani 1 1 d . . . P1 P 0.06962(7) 0.25365(8) 0.27175(4) 0.0474(3) Uani 1 1 d . . . P2 P 0.36412(6) 0.21709(8) 0.43065(4) 0.0471(3) Uani 1 1 d . . . O1 O 0.09828(15) 0.47166(17) 0.38817(10) 0.0668(9) Uani 1 1 d . . . O2 O 0.22678(16) 0.4508(2) 0.44742(11) 0.0859(10) Uani 1 1 d . . . O3 O 0.20640(15) 1.01065(19) 0.78214(10) 0.0702(9) Uani 1 1 d . . . O4 O 0.33568(16) 1.04091(18) 0.83792(10) 0.0735(9) Uani 1 1 d . . . O5 O 0.3116(3) 0.6357(3) 0.61919(16) 0.205(2) Uani 1 1 d . . . N1 N 0.2055(2) 0.7589(3) 0.61606(15) 0.1095(14) Uani 1 1 d . . . N2 N 0.2667(3) 0.7211(3) 0.62897(18) 0.1169(15) Uani 1 1 d . . . C1 C -0.0380(2) 0.2832(3) 0.22887(14) 0.0501(12) Uani 1 1 d . . . C2 C -0.0959(2) 0.3413(3) 0.25825(16) 0.0720(14) Uani 1 1 d . . . H2 H -0.0794 0.3629 0.2981 0.086 Uiso 1 1 calc R . . C3 C -0.1774(2) 0.3671(3) 0.22909(16) 0.0804(15) Uani 1 1 d . . . H3 H -0.2158 0.4065 0.2495 0.096 Uiso 1 1 calc R . . C4 C -0.2044(2) 0.3369(3) 0.17068(17) 0.0812(16) Uani 1 1 d . . . H4 H -0.2603 0.3556 0.1514 0.097 Uiso 1 1 calc R . . C5 C -0.1487(3) 0.2797(3) 0.14181(17) 0.0898(17) Uani 1 1 d . . . H5 H -0.1667 0.2583 0.1021 0.108 Uiso 1 1 calc R . . C6 C -0.0642(2) 0.2512(3) 0.16986(16) 0.0764(15) Uani 1 1 d . . . H6 H -0.0263 0.2115 0.1492 0.092 Uiso 1 1 calc R . . C7 C 0.0445(2) 0.1442(2) 0.31835(14) 0.0459(11) Uani 1 1 d . . . C8 C -0.0287(2) 0.0787(2) 0.30437(14) 0.0489(12) Uani 1 1 d . . . H8 H -0.0658 0.0892 0.2682 0.059 Uiso 1 1 calc R . . C9 C -0.0478(2) -0.0007(3) 0.34205(15) 0.0637(14) Uani 1 1 d . . . H9 H -0.0970 -0.0436 0.3316 0.076 Uiso 1 1 calc R . . C10 C 0.0073(2) -0.0160(3) 0.39598(16) 0.0684(14) Uani 1 1 d . . . H10 H -0.0048 -0.0699 0.4219 0.082 Uiso 1 1 calc R . . C11 C 0.0798(2) 0.0480(3) 0.41160(16) 0.0754(15) Uani 1 1 d . . . H11 H 0.1163 0.0377 0.4480 0.090 Uiso 1 1 calc R . . C12 C 0.0978(2) 0.1272(3) 0.37309(14) 0.0604(13) Uani 1 1 d . . . H12 H 0.1467 0.1703 0.3839 0.073 Uiso 1 1 calc R . . C13 C 0.1385(2) 0.1953(3) 0.21841(13) 0.0456(11) Uani 1 1 d . . . C14 C 0.1159(2) 0.1008(3) 0.18889(15) 0.0652(13) Uani 1 1 d . . . H14 H 0.0650 0.0649 0.1964 0.078 Uiso 1 1 calc R . . C15 C 0.1697(3) 0.0606(3) 0.14832(16) 0.0867(16) Uani 1 1 d . . . H15 H 0.1540 -0.0012 0.1276 0.104 Uiso 1 1 calc R . . C16 C 0.2472(3) 0.1132(3) 0.13878(16) 0.0882(16) Uani 1 1 d . . . H16 H 0.2844 0.0850 0.1128 0.106 Uiso 1 1 calc R . . C17 C 0.2682(3) 0.2046(3) 0.16712(15) 0.0791(16) Uani 1 1 d . . . H17 H 0.3191 0.2404 0.1597 0.095 Uiso 1 1 calc R . . C18 C 0.2141(2) 0.2462(3) 0.20766(14) 0.0598(13) Uani 1 1 d . . . H18 H 0.2298 0.3090 0.2274 0.072 Uiso 1 1 calc R . . C19 C 0.3086(2) 0.1282(3) 0.47762(14) 0.0455(11) Uani 1 1 d . . . C20 C 0.2559(2) 0.1705(3) 0.51725(15) 0.0585(13) Uani 1 1 d . . . H20 H 0.2470 0.2425 0.5179 0.070 Uiso 1 1 calc R . . C21 C 0.2151(2) 0.1055(3) 0.55706(15) 0.0674(14) Uani 1 1 d . . . H21 H 0.1799 0.1353 0.5839 0.081 Uiso 1 1 calc R . . C22 C 0.2268(2) -0.0015(3) 0.55658(15) 0.0632(14) Uani 1 1 d . . . H22 H 0.1989 -0.0440 0.5825 0.076 Uiso 1 1 calc R . . C23 C 0.2797(2) -0.0446(3) 0.51774(16) 0.0644(14) Uani 1 1 d . . . H23 H 0.2881 -0.1168 0.5169 0.077 Uiso 1 1 calc R . . C24 C 0.3204(2) 0.0201(3) 0.47974(15) 0.0581(13) Uani 1 1 d . . . H24 H 0.3575 -0.0101 0.4543 0.070 Uiso 1 1 calc R . . C25 C 0.4108(2) 0.1288(2) 0.37988(13) 0.0395(11) Uani 1 1 d . . . C26 C 0.3592(2) 0.0955(3) 0.32664(15) 0.0661(14) Uani 1 1 d . . . H26 H 0.3022 0.1225 0.3168 0.079 Uiso 1 1 calc R . . C27 C 0.3905(2) 0.0243(3) 0.28868(17) 0.0783(16) Uani 1 1 d . . . H27 H 0.3552 0.0042 0.2532 0.094 Uiso 1 1 calc R . . C28 C 0.4731(3) -0.0172(3) 0.30261(16) 0.0749(15) Uani 1 1 d . . . H28 H 0.4939 -0.0663 0.2769 0.090 Uiso 1 1 calc R . . C29 C 0.5262(2) 0.0131(3) 0.35464(15) 0.0653(14) Uani 1 1 d . . . H29 H 0.5831 -0.0145 0.3637 0.078 Uiso 1 1 calc R . . C30 C 0.4946(2) 0.0846(3) 0.39348(14) 0.0517(12) Uani 1 1 d . . . H30 H 0.5300 0.1034 0.4292 0.062 Uiso 1 1 calc R . . C31 C 0.4585(2) 0.2611(2) 0.48153(13) 0.0438(11) Uani 1 1 d . . . C32 C 0.4930(2) 0.2103(3) 0.53477(15) 0.0647(14) Uani 1 1 d . . . H32 H 0.4652 0.1497 0.5460 0.078 Uiso 1 1 calc R . . C33 C 0.5675(2) 0.2468(3) 0.57179(16) 0.0792(16) Uani 1 1 d . . . H33 H 0.5889 0.2110 0.6071 0.095 Uiso 1 1 calc R . . C34 C 0.6092(3) 0.3356(3) 0.55602(17) 0.0805(16) Uani 1 1 d . . . H34 H 0.6596 0.3602 0.5802 0.097 Uiso 1 1 calc R . . C35 C 0.5768(2) 0.3875(3) 0.50483(16) 0.0750(15) Uani 1 1 d . . . H35 H 0.6045 0.4489 0.4947 0.090 Uiso 1 1 calc R . . C36 C 0.5031(2) 0.3511(3) 0.46726(15) 0.0607(13) Uani 1 1 d . . . H36 H 0.4832 0.3875 0.4319 0.073 Uiso 1 1 calc R . . C37 C 0.1520(3) 0.4924(3) 0.43579(15) 0.0527(13) Uani 1 1 d . . . C38 C 0.1244(2) 0.5743(2) 0.47689(14) 0.0421(11) Uani 1 1 d . . . C39 C 0.1849(2) 0.6138(3) 0.52367(13) 0.0555(12) Uani 1 1 d . . . H39 H 0.2431 0.5890 0.5298 0.067 Uiso 1 1 calc R . . C40 C 0.1575(3) 0.6900(3) 0.56062(15) 0.0748(15) Uani 1 1 d . . . C41 C 0.0729(3) 0.7285(3) 0.55214(16) 0.0842(17) Uani 1 1 d . . . H41 H 0.0562 0.7818 0.5769 0.101 Uiso 1 1 calc R . . C42 C 0.0127(3) 0.6881(3) 0.50691(15) 0.0718(15) Uani 1 1 d . . . H42 H -0.0457 0.7123 0.5014 0.086 Uiso 1 1 calc R . . C43 C 0.0393(2) 0.6115(3) 0.46981(14) 0.0576(13) Uani 1 1 d . . . H43 H -0.0017 0.5843 0.4391 0.069 Uiso 1 1 calc R . . C44 C 0.3193(3) 0.7818(3) 0.68628(15) 0.0711(15) Uani 1 1 d . . . C45 C 0.4052(2) 0.7467(3) 0.70513(15) 0.0673(14) Uani 1 1 d . . . H45 H 0.4294 0.6921 0.6849 0.081 Uiso 1 1 calc R . . C46 C 0.4525(2) 0.7929(3) 0.75317(15) 0.0660(14) Uani 1 1 d . . . H46 H 0.5106 0.7715 0.7660 0.079 Uiso 1 1 calc R . . C47 C 0.4141(2) 0.8734(3) 0.78376(14) 0.0549(12) Uani 1 1 d . . . H47A H 0.4466 0.9051 0.8172 0.066 Uiso 1 1 calc R . . C48 C 0.3293(2) 0.9057(3) 0.76493(14) 0.0470(12) Uani 1 1 d . . . C49 C 0.2806(2) 0.8597(3) 0.71492(15) 0.0559(13) Uani 1 1 d . . . H49A H 0.2229 0.8816 0.7014 0.067 Uiso 1 1 calc R . . C50 C 0.2872(3) 0.9918(3) 0.79730(16) 0.0543(13) 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 0.0523(3) 0.0544(3) 0.0575(3) -0.0103(3) -0.0013(2) -0.0046(3) Cu2 0.0547(3) 0.0550(3) 0.0664(3) 0.0104(3) -0.0034(3) 0.0076(3) P1 0.0471(7) 0.0508(7) 0.0431(6) -0.0075(5) 0.0011(5) -0.0016(6) P2 0.0424(6) 0.0506(7) 0.0467(6) 0.0059(6) 0.0001(5) -0.0012(6) O1 0.0721(18) 0.0625(18) 0.0668(17) -0.0339(14) 0.0128(15) -0.0036(16) O2 0.080(2) 0.085(2) 0.096(2) 0.0071(16) 0.0238(17) 0.0433(17) O3 0.0535(17) 0.079(2) 0.0764(18) -0.0042(15) 0.0008(15) 0.0243(16) O4 0.0690(19) 0.0662(18) 0.0847(19) -0.0315(15) 0.0076(16) 0.0060(16) O5 0.222(4) 0.229(5) 0.156(3) -0.030(3) -0.010(3) -0.038(4) N1 0.135(3) 0.078(3) 0.130(3) 0.025(2) 0.070(2) 0.053(2) N2 0.146(3) 0.056(3) 0.173(3) 0.036(3) 0.116(3) 0.052(2) C1 0.047(2) 0.058(3) 0.039(2) -0.003(2) -0.015(2) -0.013(2) C2 0.057(3) 0.097(3) 0.059(3) -0.002(2) -0.007(2) 0.035(3) C3 0.062(3) 0.096(3) 0.078(3) -0.012(3) -0.011(2) 0.023(3) C4 0.048(3) 0.072(3) 0.115(4) -0.004(3) -0.021(3) 0.011(2) C5 0.074(3) 0.106(4) 0.079(3) -0.024(3) -0.033(3) 0.017(3) C6 0.056(3) 0.090(3) 0.077(3) -0.016(3) -0.018(2) 0.023(3) C7 0.043(2) 0.041(2) 0.052(2) -0.010(2) -0.0019(19) 0.004(2) C8 0.047(2) 0.050(3) 0.048(2) -0.011(2) -0.0013(19) -0.010(2) C9 0.053(3) 0.068(3) 0.066(3) -0.002(2) -0.008(2) -0.006(2) C10 0.067(3) 0.071(3) 0.065(3) 0.015(2) 0.000(2) -0.006(3) C11 0.064(3) 0.091(3) 0.063(3) 0.029(2) -0.022(2) -0.002(3) C12 0.055(3) 0.064(3) 0.056(3) 0.002(2) -0.018(2) -0.017(2) C13 0.048(2) 0.053(3) 0.034(2) 0.0005(19) -0.0006(19) -0.001(2) C14 0.072(3) 0.060(3) 0.064(3) -0.004(2) 0.012(2) 0.010(2) C15 0.116(4) 0.079(3) 0.070(3) -0.014(3) 0.028(3) 0.030(3) C16 0.092(3) 0.121(4) 0.055(3) -0.001(3) 0.023(3) 0.049(3) C17 0.080(3) 0.107(4) 0.055(3) 0.008(3) 0.029(2) 0.019(3) C18 0.066(3) 0.062(3) 0.049(2) 0.001(2) -0.002(2) 0.008(2) C19 0.044(2) 0.045(2) 0.045(2) 0.007(2) -0.0037(18) -0.001(2) C20 0.056(3) 0.054(3) 0.064(3) -0.003(2) 0.004(2) -0.005(2) C21 0.057(3) 0.098(3) 0.051(2) -0.017(2) 0.023(2) -0.010(3) C22 0.064(3) 0.065(3) 0.056(3) 0.018(2) -0.009(2) -0.005(3) C23 0.061(3) 0.053(3) 0.076(3) 0.027(2) -0.004(2) -0.001(2) C24 0.048(3) 0.065(3) 0.060(3) 0.016(2) -0.001(2) 0.008(2) C25 0.037(2) 0.043(2) 0.037(2) 0.0033(19) -0.0027(17) -0.001(2) C26 0.051(3) 0.087(3) 0.059(3) -0.005(2) 0.003(2) -0.006(3) C27 0.066(3) 0.096(4) 0.075(3) -0.015(3) 0.015(3) -0.013(3) C28 0.095(3) 0.066(3) 0.069(3) -0.007(2) 0.029(3) -0.020(3) C29 0.063(3) 0.068(3) 0.066(3) 0.011(2) 0.014(2) 0.025(2) C30 0.062(3) 0.051(3) 0.042(2) 0.003(2) 0.004(2) 0.011(2) C31 0.048(2) 0.037(2) 0.046(2) 0.0013(19) 0.005(2) 0.000(2) C32 0.067(3) 0.059(3) 0.064(3) 0.002(2) -0.007(2) -0.003(2) C33 0.071(3) 0.099(4) 0.059(3) -0.004(3) -0.024(3) 0.006(3) C34 0.067(3) 0.088(4) 0.083(3) -0.023(3) -0.006(3) -0.009(3) C35 0.064(3) 0.077(3) 0.086(3) -0.012(3) 0.015(2) -0.011(3) C36 0.057(3) 0.065(3) 0.058(3) 0.004(2) 0.002(2) -0.002(2) C37 0.073(3) 0.035(2) 0.053(3) -0.002(2) 0.019(2) -0.005(2) C38 0.046(2) 0.044(2) 0.036(2) -0.0062(19) 0.0046(19) 0.000(2) C39 0.053(2) 0.072(3) 0.038(2) 0.013(2) -0.0080(19) -0.018(2) C40 0.116(4) 0.075(3) 0.031(2) -0.011(2) 0.002(2) -0.051(3) C41 0.119(4) 0.085(4) 0.052(3) -0.022(2) 0.022(3) -0.013(3) C42 0.079(3) 0.074(3) 0.065(3) -0.014(2) 0.018(2) 0.005(3) C43 0.057(3) 0.070(3) 0.044(2) -0.007(2) -0.002(2) 0.005(2) C44 0.125(4) 0.055(3) 0.031(2) -0.011(2) 0.005(3) -0.027(3) C45 0.074(3) 0.059(3) 0.069(3) 0.009(2) 0.012(3) 0.022(3) C46 0.061(3) 0.068(3) 0.064(3) 0.004(2) -0.009(2) 0.009(3) C47 0.064(3) 0.051(3) 0.047(2) -0.003(2) -0.002(2) 0.006(2) C48 0.045(2) 0.048(3) 0.047(2) 0.002(2) 0.000(2) -0.003(2) C49 0.045(2) 0.057(3) 0.062(3) -0.001(2) -0.006(2) -0.007(2) C50 0.059(3) 0.049(3) 0.056(3) -0.005(2) 0.013(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 O1 1.954(2) . ? Cu1 O3 1.996(2) 4_575 ? Cu1 P1 2.1528(11) . ? Cu1 Cu2 2.9391(8) . ? Cu2 O4 1.988(2) 4_575 ? Cu2 O2 1.990(2) . ? Cu2 P2 2.1721(11) . ? P1 C7 1.808(3) . ? P1 C1 1.820(3) . ? P1 C13 1.834(3) . ? P2 C31 1.796(3) . ? P2 C25 1.801(3) . ? P2 C19 1.818(3) . ? O1 C37 1.278(4) . ? O2 C37 1.248(4) . ? O3 C50 1.251(4) . ? O3 Cu1 1.996(2) 4_576 ? O4 C50 1.256(4) . ? O4 Cu2 1.988(2) 4_576 ? O5 N2 1.317(5) . ? N1 N2 1.053(5) . ? N1 C40 1.609(5) . ? N2 C44 1.612(5) . ? C1 C2 1.375(4) . ? C1 C6 1.382(4) . ? C2 C3 1.359(4) . ? C2 H2 0.9300 . ? C3 C4 1.365(5) . ? C3 H3 0.9300 . ? C4 C5 1.340(5) . ? C4 H4 0.9300 . ? C5 C6 1.399(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.389(4) . ? C7 C8 1.392(4) . ? C8 C9 1.369(4) . ? C8 H8 0.9300 . ? C9 C10 1.384(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(5) . ? C10 H10 0.9300 . ? C11 C12 1.374(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.365(4) . ? C13 C14 1.394(4) . ? C14 C15 1.388(5) . ? C14 H14 0.9300 . ? C15 C16 1.392(5) . ? C15 H15 0.9300 . ? C16 C17 1.345(5) . ? C16 H16 0.9300 . ? C17 C18 1.397(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.372(4) . ? C19 C24 1.392(4) . ? C20 C21 1.411(4) . ? C20 H20 0.9300 . ? C21 C22 1.378(5) . ? C21 H21 0.9300 . ? C22 C23 1.366(5) . ? C22 H22 0.9300 . ? C23 C24 1.381(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.387(4) . ? C25 C26 1.398(4) . ? C26 C27 1.365(5) . ? C26 H26 0.9300 . ? C27 C28 1.357(5) . ? C27 H27 0.9300 . ? C28 C29 1.377(5) . ? C28 H28 0.9300 . ? C29 C30 1.383(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C36 1.390(4) . ? C31 C32 1.391(4) . ? C32 C33 1.390(5) . ? C32 H32 0.9300 . ? C33 C34 1.365(5) . ? C33 H33 0.9300 . ? C34 C35 1.353(5) . ? C34 H34 0.9300 . ? C35 C36 1.386(4) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.483(4) . ? C38 C43 1.365(4) . ? C38 C39 1.390(4) . ? C39 C40 1.371(5) . ? C39 H39 0.9300 . ? C40 C41 1.363(5) . ? C41 C42 1.369(5) . ? C41 H41 0.9300 . ? C42 C43 1.372(4) . ? C42 H42 0.9300 . ? C43 H43 0.9300 . ? C44 C49 1.353(5) . ? C44 C45 1.389(5) . ? C45 C46 1.344(4) . ? C45 H45 0.9300 . ? C46 C47 1.399(4) . ? C46 H46 0.9300 . ? C47 C48 1.363(4) . ? C47 H47A 0.9300 . ? C48 C49 1.384(4) . ? C48 C50 1.500(5) . ? C49 H49A 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 O1 Cu1 O3 100.81(10) . 4_575 ? O1 Cu1 P1 134.33(8) . . ? O3 Cu1 P1 122.82(7) 4_575 . ? O1 Cu1 Cu2 82.15(7) . . ? O3 Cu1 Cu2 78.55(7) 4_575 . ? P1 Cu1 Cu2 116.75(3) . . ? O4 Cu2 O2 102.87(10) 4_575 . ? O4 Cu2 P2 125.97(8) 4_575 . ? O2 Cu2 P2 124.43(8) . . ? O4 Cu2 Cu1 80.37(7) 4_575 . ? O2 Cu2 Cu1 76.94(7) . . ? P2 Cu2 Cu1 130.69(3) . . ? C7 P1 C1 102.67(15) . . ? C7 P1 C13 103.59(15) . . ? C1 P1 C13 106.96(15) . . ? C7 P1 Cu1 116.53(11) . . ? C1 P1 Cu1 111.44(12) . . ? C13 P1 Cu1 114.52(11) . . ? C31 P2 C25 104.18(15) . . ? C31 P2 C19 102.90(14) . . ? C25 P2 C19 102.49(15) . . ? C31 P2 Cu2 104.87(11) . . ? C25 P2 Cu2 121.44(11) . . ? C19 P2 Cu2 118.66(11) . . ? C37 O1 Cu1 125.5(2) . . ? C37 O2 Cu2 131.4(2) . . ? C50 O3 Cu1 129.3(2) . 4_576 ? C50 O4 Cu2 126.9(2) . 4_576 ? N2 N1 C40 104.8(4) . . ? N1 N2 O5 142.2(5) . . ? N1 N2 C44 109.0(4) . . ? O5 N2 C44 108.3(3) . . ? C2 C1 C6 119.1(3) . . ? C2 C1 P1 116.5(2) . . ? C6 C1 P1 124.4(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 121.9(4) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 118.5(4) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 121.7(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C1 C6 C5 118.8(4) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C12 C7 C8 117.4(3) . . ? C12 C7 P1 118.7(3) . . ? C8 C7 P1 123.8(2) . . ? C9 C8 C7 122.2(3) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C8 C9 C10 118.8(3) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 119.7(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 121.4(3) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? C18 C13 C14 119.4(3) . . ? C18 C13 P1 118.6(3) . . ? C14 C13 P1 122.0(3) . . ? C15 C14 C13 119.7(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 119.8(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.1(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.6(4) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.4(3) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C24 116.8(3) . . ? C20 C19 P2 118.2(3) . . ? C24 C19 P2 124.9(3) . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 120.7(3) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 119.4(4) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 119.3(4) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C23 C24 C19 123.3(3) . . ? C23 C24 H24 118.4 . . ? C19 C24 H24 118.4 . . ? C30 C25 C26 117.2(3) . . ? C30 C25 P2 122.6(2) . . ? C26 C25 P2 119.9(2) . . ? C27 C26 C25 121.7(3) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C28 C27 C26 120.1(4) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.3(4) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C28 C29 C30 119.8(4) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C29 C30 C25 120.8(3) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? C36 C31 C32 116.0(3) . . ? C36 C31 P2 119.1(2) . . ? C32 C31 P2 124.9(3) . . ? C33 C32 C31 122.4(4) . . ? C33 C32 H32 118.8 . . ? C31 C32 H32 118.8 . . ? C34 C33 C32 119.6(4) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C35 C34 C33 119.5(4) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 121.3(4) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C35 C36 C31 121.2(3) . . ? C35 C36 H36 119.4 . . ? C31 C36 H36 119.4 . . ? O2 C37 O1 123.3(3) . . ? O2 C37 C38 119.5(3) . . ? O1 C37 C38 117.1(3) . . ? C43 C38 C39 118.9(3) . . ? C43 C38 C37 120.7(3) . . ? C39 C38 C37 120.4(3) . . ? C40 C39 C38 118.9(3) . . ? C40 C39 H39 120.5 . . ? C38 C39 H39 120.5 . . ? C41 C40 C39 121.6(4) . . ? C41 C40 N1 103.5(3) . . ? C39 C40 N1 134.7(4) . . ? C40 C41 C42 119.5(4) . . ? C40 C41 H41 120.3 . . ? C42 C41 H41 120.3 . . ? C41 C42 C43 119.4(4) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C38 C43 C42 121.6(3) . . ? C38 C43 H43 119.2 . . ? C42 C43 H43 119.2 . . ? C49 C44 C45 122.7(3) . . ? C49 C44 N2 121.6(4) . . ? C45 C44 N2 115.7(3) . . ? C46 C45 C44 118.8(4) . . ? C46 C45 H45 120.6 . . ? C44 C45 H45 120.6 . . ? C45 C46 C47 119.7(3) . . ? C45 C46 H46 120.2 . . ? C47 C46 H46 120.2 . . ? C48 C47 C46 120.5(3) . . ? C48 C47 H47A 119.8 . . ? C46 C47 H47A 119.8 . . ? C47 C48 C49 120.2(3) . . ? C47 C48 C50 121.1(3) . . ? C49 C48 C50 118.7(3) . . ? C44 C49 C48 118.0(3) . . ? C44 C49 H49A 121.0 . . ? C48 C49 H49A 121.0 . . ? O3 C50 O4 124.1(3) . . ? O3 C50 C48 118.2(3) . . ? O4 C50 C48 117.7(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 O1 Cu1 Cu2 O4 -106.62(10) . . . 4_575 ? O3 Cu1 Cu2 O4 -3.85(10) 4_575 . . 4_575 ? P1 Cu1 Cu2 O4 117.29(8) . . . 4_575 ? O1 Cu1 Cu2 O2 -0.88(10) . . . . ? O3 Cu1 Cu2 O2 101.88(10) 4_575 . . . ? P1 Cu1 Cu2 O2 -136.97(8) . . . . ? O1 Cu1 Cu2 P2 123.60(8) . . . . ? O3 Cu1 Cu2 P2 -133.64(8) 4_575 . . . ? P1 Cu1 Cu2 P2 -12.49(6) . . . . ? O1 Cu1 P1 C7 -47.30(16) . . . . ? O3 Cu1 P1 C7 152.36(14) 4_575 . . . ? Cu2 Cu1 P1 C7 58.89(13) . . . . ? O1 Cu1 P1 C1 70.05(16) . . . . ? O3 Cu1 P1 C1 -90.30(15) 4_575 . . . ? Cu2 Cu1 P1 C1 176.23(11) . . . . ? O1 Cu1 P1 C13 -168.38(14) . . . . ? O3 Cu1 P1 C13 31.27(15) 4_575 . . . ? Cu2 Cu1 P1 C13 -62.20(12) . . . . ? O4 Cu2 P2 C31 74.05(14) 4_575 . . . ? O2 Cu2 P2 C31 -72.17(15) . . . . ? Cu1 Cu2 P2 C31 -175.36(11) . . . . ? O4 Cu2 P2 C25 -43.30(16) 4_575 . . . ? O2 Cu2 P2 C25 170.48(15) . . . . ? Cu1 Cu2 P2 C25 67.29(13) . . . . ? O4 Cu2 P2 C19 -171.84(14) 4_575 . . . ? O2 Cu2 P2 C19 41.94(16) . . . . ? Cu1 Cu2 P2 C19 -61.25(13) . . . . ? O3 Cu1 O1 C37 -71.2(3) 4_575 . . . ? P1 Cu1 O1 C37 125.5(3) . . . . ? Cu2 Cu1 O1 C37 5.5(3) . . . . ? O4 Cu2 O2 C37 73.1(3) 4_575 . . . ? P2 Cu2 O2 C37 -134.4(3) . . . . ? Cu1 Cu2 O2 C37 -3.7(3) . . . . ? C40 N1 N2 O5 -8.1(8) . . . . ? C40 N1 N2 C44 -178.0(3) . . . . ? C7 P1 C1 C2 80.3(3) . . . . ? C13 P1 C1 C2 -171.0(3) . . . . ? Cu1 P1 C1 C2 -45.1(3) . . . . ? C7 P1 C1 C6 -99.7(3) . . . . ? C13 P1 C1 C6 9.0(4) . . . . ? Cu1 P1 C1 C6 134.9(3) . . . . ? C6 C1 C2 C3 -0.5(6) . . . . ? P1 C1 C2 C3 179.5(3) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C2 C1 C6 C5 0.4(6) . . . . ? P1 C1 C6 C5 -179.6(3) . . . . ? C4 C5 C6 C1 0.0(6) . . . . ? C1 P1 C7 C12 -153.8(3) . . . . ? C13 P1 C7 C12 95.0(3) . . . . ? Cu1 P1 C7 C12 -31.7(3) . . . . ? C1 P1 C7 C8 22.4(3) . . . . ? C13 P1 C7 C8 -88.8(3) . . . . ? Cu1 P1 C7 C8 144.4(2) . . . . ? C12 C7 C8 C9 -0.8(5) . . . . ? P1 C7 C8 C9 -177.1(3) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C9 C10 C11 C12 -0.4(6) . . . . ? C10 C11 C12 C7 -0.2(6) . . . . ? C8 C7 C12 C11 0.8(5) . . . . ? P1 C7 C12 C11 177.2(3) . . . . ? C7 P1 C13 C18 -134.6(3) . . . . ? C1 P1 C13 C18 117.4(3) . . . . ? Cu1 P1 C13 C18 -6.6(3) . . . . ? C7 P1 C13 C14 45.3(3) . . . . ? C1 P1 C13 C14 -62.8(3) . . . . ? Cu1 P1 C13 C14 173.2(2) . . . . ? C18 C13 C14 C15 -1.0(5) . . . . ? P1 C13 C14 C15 179.2(3) . . . . ? C13 C14 C15 C16 2.0(5) . . . . ? C14 C15 C16 C17 -2.4(6) . . . . ? C15 C16 C17 C18 1.9(6) . . . . ? C14 C13 C18 C17 0.4(5) . . . . ? P1 C13 C18 C17 -179.7(3) . . . . ? C16 C17 C18 C13 -0.9(5) . . . . ? C31 P2 C19 C20 79.9(3) . . . . ? C25 P2 C19 C20 -172.1(2) . . . . ? Cu2 P2 C19 C20 -35.2(3) . . . . ? C31 P2 C19 C24 -95.2(3) . . . . ? C25 P2 C19 C24 12.7(3) . . . . ? Cu2 P2 C19 C24 149.6(2) . . . . ? C24 C19 C20 C21 -1.1(5) . . . . ? P2 C19 C20 C21 -176.6(2) . . . . ? C19 C20 C21 C22 -0.5(5) . . . . ? C20 C21 C22 C23 1.0(5) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C22 C23 C24 C19 -1.7(5) . . . . ? C20 C19 C24 C23 2.2(5) . . . . ? P2 C19 C24 C23 177.4(3) . . . . ? C31 P2 C25 C30 18.2(3) . . . . ? C19 P2 C25 C30 -88.8(3) . . . . ? Cu2 P2 C25 C30 135.9(2) . . . . ? C31 P2 C25 C26 -167.2(3) . . . . ? C19 P2 C25 C26 85.8(3) . . . . ? Cu2 P2 C25 C26 -49.5(3) . . . . ? C30 C25 C26 C27 -1.5(5) . . . . ? P2 C25 C26 C27 -176.4(3) . . . . ? C25 C26 C27 C28 0.9(6) . . . . ? C26 C27 C28 C29 -0.7(6) . . . . ? C27 C28 C29 C30 1.2(6) . . . . ? C28 C29 C30 C25 -1.8(5) . . . . ? C26 C25 C30 C29 2.0(5) . . . . ? P2 C25 C30 C29 176.7(3) . . . . ? C25 P2 C31 C36 91.0(3) . . . . ? C19 P2 C31 C36 -162.4(3) . . . . ? Cu2 P2 C31 C36 -37.6(3) . . . . ? C25 P2 C31 C32 -87.5(3) . . . . ? C19 P2 C31 C32 19.1(3) . . . . ? Cu2 P2 C31 C32 143.9(3) . . . . ? C36 C31 C32 C33 0.1(5) . . . . ? P2 C31 C32 C33 178.6(3) . . . . ? C31 C32 C33 C34 0.0(6) . . . . ? C32 C33 C34 C35 0.8(6) . . . . ? C33 C34 C35 C36 -1.5(6) . . . . ? C34 C35 C36 C31 1.5(6) . . . . ? C32 C31 C36 C35 -0.8(5) . . . . ? P2 C31 C36 C35 -179.4(3) . . . . ? Cu2 O2 C37 O1 9.1(6) . . . . ? Cu2 O2 C37 C38 -167.6(2) . . . . ? Cu1 O1 C37 O2 -9.9(5) . . . . ? Cu1 O1 C37 C38 166.9(2) . . . . ? O2 C37 C38 C43 -171.6(3) . . . . ? O1 C37 C38 C43 11.5(5) . . . . ? O2 C37 C38 C39 8.0(5) . . . . ? O1 C37 C38 C39 -169.0(3) . . . . ? C43 C38 C39 C40 -0.9(5) . . . . ? C37 C38 C39 C40 179.5(3) . . . . ? C38 C39 C40 C41 -0.8(6) . . . . ? C38 C39 C40 N1 -176.4(4) . . . . ? N2 N1 C40 C41 169.3(4) . . . . ? N2 N1 C40 C39 -14.4(6) . . . . ? C39 C40 C41 C42 2.1(6) . . . . ? N1 C40 C41 C42 179.0(3) . . . . ? C40 C41 C42 C43 -1.8(6) . . . . ? C39 C38 C43 C42 1.2(5) . . . . ? C37 C38 C43 C42 -179.2(3) . . . . ? C41 C42 C43 C38 0.1(6) . . . . ? N1 N2 C44 C49 7.6(6) . . . . ? O5 N2 C44 C49 -165.9(4) . . . . ? N1 N2 C44 C45 -174.4(4) . . . . ? O5 N2 C44 C45 12.1(5) . . . . ? C49 C44 C45 C46 -1.2(6) . . . . ? N2 C44 C45 C46 -179.2(3) . . . . ? C44 C45 C46 C47 1.3(6) . . . . ? C45 C46 C47 C48 -0.5(5) . . . . ? C46 C47 C48 C49 -0.5(5) . . . . ? C46 C47 C48 C50 179.9(3) . . . . ? C45 C44 C49 C48 0.2(6) . . . . ? N2 C44 C49 C48 178.1(3) . . . . ? C47 C48 C49 C44 0.7(5) . . . . ? C50 C48 C49 C44 -179.8(3) . . . . ? Cu1 O3 C50 O4 -5.5(6) 4_576 . . . ? Cu1 O3 C50 C48 174.7(2) 4_576 . . . ? Cu2 O4 C50 O3 11.7(5) 4_576 . . . ? Cu2 O4 C50 C48 -168.6(2) 4_576 . . . ? C47 C48 C50 O3 -172.5(3) . . . . ? C49 C48 C50 O3 8.0(5) . . . . ? C47 C48 C50 O4 7.7(5) . . . . ? C49 C48 C50 O4 -171.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.558 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.072 # Attachment 'Compound 3.CIF' #========================================================================== data_xb1122 _database_code_depnum_ccdc_archive 'CCDC 651800' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N4 O4 Zn' _chemical_formula_weight 491.79 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0104(8) _cell_length_b 8.3900(8) _cell_length_c 16.5826(17) _cell_angle_alpha 101.017(2) _cell_angle_beta 96.9130(10) _cell_angle_gamma 93.6290(10) _cell_volume 1081.71(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 994 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 19.60 _exptl_crystal_description rod _exptl_crystal_colour Orange-red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 1.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7989 _exptl_absorpt_correction_T_max 0.8816 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 5535 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3792 _reflns_number_gt 2620 _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^)+(0.0670P)^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 0.0021(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3792 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.26685(6) 0.09874(6) 0.75375(3) 0.0425(2) Uani 1 1 d . . . N1 N 1.0200(6) 0.4904(6) 0.5349(3) 0.0678(13) Uani 1 1 d . . . N2 N 0.0457(5) 0.9669(5) 1.0244(3) 0.0508(10) Uani 1 1 d . . . N3 N 0.0343(4) -0.0163(4) 0.6904(2) 0.0438(10) Uani 1 1 d . . . N4 N 0.3474(4) -0.1059(5) 0.7906(3) 0.0440(10) Uani 1 1 d . . . O1 O 0.3617(5) 0.1484(5) 0.6451(2) 0.0769(12) Uani 1 1 d . . . O2 O 0.5301(5) 0.2062(4) 0.7605(2) 0.0681(11) Uani 1 1 d . . . O3 O 0.1669(4) 0.2795(4) 0.8123(2) 0.0565(9) Uani 1 1 d . . . O4 O 0.3273(5) 0.2658(4) 0.9291(2) 0.0707(11) Uani 1 1 d . . . C1 C 0.5973(7) 0.3050(9) 0.5648(4) 0.096(2) Uani 1 1 d . . . H1 H 0.4886 0.2778 0.5367 0.115 Uiso 1 1 calc R . . C2 C 0.7212(8) 0.3740(9) 0.5266(4) 0.101(3) Uani 1 1 d . . . H2 H 0.6953 0.3923 0.4731 0.121 Uiso 1 1 calc R . . C3 C 0.8796(6) 0.4142(6) 0.5676(3) 0.0572(14) Uani 1 1 d . . . C4 C 0.9174(7) 0.3855(7) 0.6457(4) 0.0666(16) Uani 1 1 d . . . H4 H 1.0261 0.4119 0.6741 0.080 Uiso 1 1 calc R . . C5 C 0.7922(6) 0.3168(6) 0.6819(3) 0.0604(14) Uani 1 1 d . . . H5 H 0.8182 0.2971 0.7351 0.073 Uiso 1 1 calc R . . C6 C 0.6340(6) 0.2773(6) 0.6428(3) 0.0510(13) Uani 1 1 d . . . C7 C 0.5010(7) 0.2037(6) 0.6856(4) 0.0549(13) Uani 1 1 d . . . C8 C 0.0486(6) 0.5690(6) 0.8817(3) 0.0491(12) Uani 1 1 d . . . H8 H -0.0051 0.5114 0.8307 0.059 Uiso 1 1 calc R . . C9 C 0.0035(6) 0.7210(6) 0.9120(3) 0.0492(12) Uani 1 1 d . . . H9 H -0.0794 0.7665 0.8817 0.059 Uiso 1 1 calc R . . C10 C 0.0820(6) 0.8065(6) 0.9883(3) 0.0448(12) Uani 1 1 d . . . C11 C 0.2029(6) 0.7367(6) 1.0337(3) 0.0525(13) Uani 1 1 d . . . H11 H 0.2537 0.7928 1.0856 0.063 Uiso 1 1 calc R . . C12 C 0.2481(6) 0.5843(6) 1.0020(3) 0.0529(13) Uani 1 1 d . . . H12 H 0.3302 0.5384 1.0326 0.063 Uiso 1 1 calc R . . C13 C 0.1736(6) 0.4986(5) 0.9256(3) 0.0431(11) Uani 1 1 d . . . C14 C 0.2267(6) 0.3353(6) 0.8885(3) 0.0487(12) Uani 1 1 d . . . C15 C 0.3235(6) -0.2482(6) 0.7367(3) 0.0486(12) Uani 1 1 d . . . H15 H 0.2567 -0.2535 0.6861 0.058 Uiso 1 1 calc R . . C16 C 0.3922(6) -0.3869(6) 0.7520(4) 0.0589(14) Uani 1 1 d . . . H16 H 0.3720 -0.4840 0.7131 0.071 Uiso 1 1 calc R . . C17 C 0.4912(7) -0.3785(7) 0.8261(4) 0.0629(15) Uani 1 1 d . . . H17 H 0.5418 -0.4698 0.8377 0.075 Uiso 1 1 calc R . . C18 C 0.5152(7) -0.2360(7) 0.8827(4) 0.0622(15) Uani 1 1 d . . . H18 H 0.5799 -0.2295 0.9339 0.075 Uiso 1 1 calc R . . C19 C 0.4423(6) -0.1007(6) 0.8633(3) 0.0494(12) Uani 1 1 d . . . H19 H 0.4598 -0.0030 0.9019 0.059 Uiso 1 1 calc R . . C20 C -0.0800(6) -0.0485(6) 0.7387(3) 0.0536(13) Uani 1 1 d . . . H20 H -0.0512 -0.0186 0.7959 0.064 Uiso 1 1 calc R . . C21 C -0.2367(6) -0.1231(7) 0.7083(4) 0.0672(16) Uani 1 1 d . . . H21 H -0.3121 -0.1452 0.7441 0.081 Uiso 1 1 calc R . . C22 C -0.2813(7) -0.1646(8) 0.6252(4) 0.0785(19) Uani 1 1 d . . . H22 H -0.3883 -0.2145 0.6031 0.094 Uiso 1 1 calc R . . C23 C -0.1664(7) -0.1319(7) 0.5739(4) 0.0716(17) Uani 1 1 d . . . H23 H -0.1937 -0.1599 0.5166 0.086 Uiso 1 1 calc R . . C24 C -0.0111(6) -0.0572(6) 0.6092(3) 0.0573(14) Uani 1 1 d . . . H24 H 0.0663 -0.0341 0.5745 0.069 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 Zn1 0.0421(3) 0.0412(4) 0.0459(4) 0.0109(2) 0.0098(2) 0.0029(2) N1 0.065(3) 0.083(3) 0.058(3) 0.023(3) 0.009(3) -0.004(2) N2 0.063(3) 0.038(2) 0.054(3) 0.0078(18) 0.013(2) 0.011(2) N3 0.039(2) 0.048(2) 0.047(3) 0.0129(19) 0.0105(19) 0.0038(18) N4 0.040(2) 0.041(2) 0.054(3) 0.014(2) 0.010(2) 0.0036(18) O1 0.058(2) 0.098(3) 0.073(3) 0.021(2) 0.011(2) -0.023(2) O2 0.082(3) 0.071(3) 0.061(3) 0.024(2) 0.034(2) 0.000(2) O3 0.055(2) 0.052(2) 0.056(2) -0.0047(17) 0.0034(18) 0.0150(17) O4 0.090(3) 0.063(2) 0.063(3) 0.012(2) 0.009(2) 0.038(2) C1 0.052(3) 0.174(7) 0.061(4) 0.043(4) 0.001(3) -0.036(4) C2 0.076(4) 0.179(8) 0.051(4) 0.053(4) -0.002(3) -0.039(5) C3 0.049(3) 0.067(4) 0.059(4) 0.018(3) 0.018(3) -0.008(3) C4 0.055(3) 0.079(4) 0.066(4) 0.027(3) 0.000(3) -0.020(3) C5 0.061(3) 0.067(4) 0.053(3) 0.019(3) 0.006(3) -0.010(3) C6 0.047(3) 0.060(3) 0.048(3) 0.013(3) 0.015(3) -0.003(2) C7 0.052(3) 0.047(3) 0.069(4) 0.012(3) 0.022(3) 0.004(3) C8 0.053(3) 0.043(3) 0.048(3) 0.002(2) 0.000(2) 0.003(2) C9 0.051(3) 0.038(3) 0.056(3) 0.009(2) -0.002(3) 0.005(2) C10 0.050(3) 0.039(3) 0.049(3) 0.014(2) 0.013(2) 0.006(2) C11 0.064(3) 0.044(3) 0.045(3) 0.002(2) 0.003(3) 0.001(3) C12 0.058(3) 0.052(3) 0.050(3) 0.013(3) 0.003(3) 0.012(3) C13 0.045(3) 0.039(3) 0.048(3) 0.009(2) 0.013(2) 0.006(2) C14 0.046(3) 0.050(3) 0.052(3) 0.008(3) 0.016(3) 0.002(2) C15 0.049(3) 0.043(3) 0.056(3) 0.015(2) 0.009(2) 0.000(2) C16 0.062(3) 0.039(3) 0.076(4) 0.012(3) 0.010(3) 0.002(3) C17 0.057(3) 0.062(4) 0.080(4) 0.032(3) 0.019(3) 0.016(3) C18 0.066(4) 0.072(4) 0.055(4) 0.023(3) 0.008(3) 0.019(3) C19 0.049(3) 0.049(3) 0.050(3) 0.009(2) 0.005(2) 0.006(2) C20 0.053(3) 0.064(3) 0.046(3) 0.016(3) 0.007(3) -0.003(3) C21 0.046(3) 0.078(4) 0.079(4) 0.020(3) 0.016(3) -0.011(3) C22 0.050(3) 0.112(5) 0.064(4) 0.008(4) -0.001(3) -0.022(3) C23 0.067(4) 0.095(5) 0.046(3) 0.009(3) -0.004(3) -0.013(3) C24 0.053(3) 0.071(4) 0.049(3) 0.014(3) 0.014(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.914(3) . ? Zn1 N4 2.046(4) . ? Zn1 N3 2.102(4) . ? Zn1 O1 2.138(4) . ? Zn1 O2 2.221(4) . ? N1 N1 1.207(8) 2_766 ? N1 C3 1.468(6) . ? N2 N2 1.258(7) 2_577 ? N2 C10 1.427(6) . ? N3 C24 1.325(6) . ? N3 C20 1.335(6) . ? N4 C15 1.335(6) . ? N4 C19 1.337(6) . ? O1 C7 1.244(6) . ? O2 C7 1.232(6) . ? O3 C14 1.281(6) . ? O4 C14 1.234(6) . ? C1 C6 1.358(7) . ? C1 C2 1.393(7) . ? C1 H1 0.9300 . ? C2 C3 1.355(7) . ? C2 H2 0.9300 . ? C3 C4 1.364(7) . ? C4 C5 1.380(7) . ? C4 H4 0.9300 . ? C5 C6 1.343(6) . ? C5 H5 0.9300 . ? C6 C7 1.513(7) . ? C8 C9 1.366(6) . ? C8 C13 1.395(6) . ? C8 H8 0.9300 . ? C9 C10 1.384(6) . ? C9 H9 0.9300 . ? C10 C11 1.383(6) . ? C11 C12 1.375(6) . ? C11 H11 0.9300 . ? C12 C13 1.375(6) . ? C12 H12 0.9300 . ? C13 C14 1.501(6) . ? C15 C16 1.373(6) . ? C15 H15 0.9300 . ? C16 C17 1.366(7) . ? C16 H16 0.9300 . ? C17 C18 1.359(7) . ? C17 H17 0.9300 . ? C18 C19 1.383(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.360(7) . ? C20 H20 0.9300 . ? C21 C22 1.352(8) . ? C21 H21 0.9300 . ? C22 C23 1.375(7) . ? C22 H22 0.9300 . ? C23 C24 1.367(7) . ? C23 H23 0.9300 . ? C24 H24 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 O3 Zn1 N4 130.66(16) . . ? O3 Zn1 N3 93.75(14) . . ? N4 Zn1 N3 94.85(15) . . ? O3 Zn1 O1 112.95(16) . . ? N4 Zn1 O1 114.53(16) . . ? N3 Zn1 O1 94.93(15) . . ? O3 Zn1 O2 100.89(15) . . ? N4 Zn1 O2 91.99(14) . . ? N3 Zn1 O2 153.73(15) . . ? O1 Zn1 O2 59.31(14) . . ? N1 N1 C3 112.1(6) 2_766 . ? N2 N2 C10 113.5(5) 2_577 . ? C24 N3 C20 117.3(4) . . ? C24 N3 Zn1 127.5(3) . . ? C20 N3 Zn1 115.2(3) . . ? C15 N4 C19 117.6(4) . . ? C15 N4 Zn1 119.3(3) . . ? C19 N4 Zn1 122.6(3) . . ? C7 O1 Zn1 91.4(3) . . ? C7 O2 Zn1 87.9(3) . . ? C14 O3 Zn1 117.8(3) . . ? C6 C1 C2 120.6(5) . . ? C6 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 119.8(6) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.9(5) . . ? C2 C3 N1 125.0(5) . . ? C4 C3 N1 115.1(5) . . ? C3 C4 C5 119.0(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 122.1(5) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C1 118.6(5) . . ? C5 C6 C7 120.0(5) . . ? C1 C6 C7 121.4(5) . . ? O2 C7 O1 121.3(5) . . ? O2 C7 C6 119.4(5) . . ? O1 C7 C6 119.2(5) . . ? C9 C8 C13 121.4(5) . . ? C9 C8 H8 119.3 . . ? C13 C8 H8 119.3 . . ? C8 C9 C10 119.5(4) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 119.9(4) . . ? C11 C10 N2 116.6(4) . . ? C9 C10 N2 123.6(4) . . ? C12 C11 C10 120.0(5) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 121.0(5) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C8 118.3(4) . . ? C12 C13 C14 121.6(4) . . ? C8 C13 C14 120.0(5) . . ? O4 C14 O3 123.6(5) . . ? O4 C14 C13 120.7(5) . . ? O3 C14 C13 115.6(4) . . ? N4 C15 C16 123.3(5) . . ? N4 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C17 C16 C15 118.3(5) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C18 C17 C16 119.6(5) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 119.2(5) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? N4 C19 C18 122.0(5) . . ? N4 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? N3 C20 C21 123.1(5) . . ? N3 C20 H20 118.4 . . ? C21 C20 H20 118.4 . . ? C22 C21 C20 119.0(5) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 119.1(5) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C24 C23 C22 118.5(5) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? N3 C24 C23 123.0(5) . . ? N3 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 N3 C24 121.7(4) . . . . ? N4 Zn1 N3 C24 -107.0(4) . . . . ? O1 Zn1 N3 C24 8.2(4) . . . . ? O2 Zn1 N3 C24 -2.5(6) . . . . ? O3 Zn1 N3 C20 -57.2(3) . . . . ? N4 Zn1 N3 C20 74.2(3) . . . . ? O1 Zn1 N3 C20 -170.7(3) . . . . ? O2 Zn1 N3 C20 178.7(3) . . . . ? O3 Zn1 N4 C15 142.2(3) . . . . ? N3 Zn1 N4 C15 43.0(4) . . . . ? O1 Zn1 N4 C15 -54.6(4) . . . . ? O2 Zn1 N4 C15 -111.6(3) . . . . ? O3 Zn1 N4 C19 -46.5(4) . . . . ? N3 Zn1 N4 C19 -145.6(4) . . . . ? O1 Zn1 N4 C19 116.7(4) . . . . ? O2 Zn1 N4 C19 59.7(4) . . . . ? O3 Zn1 O1 C7 88.5(3) . . . . ? N4 Zn1 O1 C7 -77.7(3) . . . . ? N3 Zn1 O1 C7 -175.3(3) . . . . ? O2 Zn1 O1 C7 -0.7(3) . . . . ? O3 Zn1 O2 C7 -109.6(3) . . . . ? N4 Zn1 O2 C7 118.3(3) . . . . ? N3 Zn1 O2 C7 13.1(5) . . . . ? O1 Zn1 O2 C7 0.7(3) . . . . ? N4 Zn1 O3 C14 40.8(4) . . . . ? N3 Zn1 O3 C14 140.4(4) . . . . ? O1 Zn1 O3 C14 -122.6(4) . . . . ? O2 Zn1 O3 C14 -61.5(4) . . . . ? C6 C1 C2 C3 -0.2(12) . . . . ? C1 C2 C3 C4 0.6(11) . . . . ? C1 C2 C3 N1 -178.7(6) . . . . ? N1 N1 C3 C2 -2.2(10) 2_766 . . . ? N1 N1 C3 C4 178.5(6) 2_766 . . . ? C2 C3 C4 C5 -0.5(9) . . . . ? N1 C3 C4 C5 178.9(5) . . . . ? C3 C4 C5 C6 -0.1(9) . . . . ? C4 C5 C6 C1 0.6(9) . . . . ? C4 C5 C6 C7 -179.4(5) . . . . ? C2 C1 C6 C5 -0.4(10) . . . . ? C2 C1 C6 C7 179.6(6) . . . . ? Zn1 O2 C7 O1 -1.3(5) . . . . ? Zn1 O2 C7 C6 175.5(4) . . . . ? Zn1 O1 C7 O2 1.3(5) . . . . ? Zn1 O1 C7 C6 -175.4(4) . . . . ? C5 C6 C7 O2 12.4(8) . . . . ? C1 C6 C7 O2 -167.5(6) . . . . ? C5 C6 C7 O1 -170.7(5) . . . . ? C1 C6 C7 O1 9.3(8) . . . . ? C13 C8 C9 C10 -0.6(7) . . . . ? C8 C9 C10 C11 -1.1(7) . . . . ? C8 C9 C10 N2 178.8(4) . . . . ? N2 N2 C10 C11 170.1(5) 2_577 . . . ? N2 N2 C10 C9 -9.8(8) 2_577 . . . ? C9 C10 C11 C12 1.7(7) . . . . ? N2 C10 C11 C12 -178.2(4) . . . . ? C10 C11 C12 C13 -0.6(7) . . . . ? C11 C12 C13 C8 -1.1(7) . . . . ? C11 C12 C13 C14 177.3(4) . . . . ? C9 C8 C13 C12 1.7(7) . . . . ? C9 C8 C13 C14 -176.7(4) . . . . ? Zn1 O3 C14 O4 -10.7(7) . . . . ? Zn1 O3 C14 C13 166.2(3) . . . . ? C12 C13 C14 O4 7.3(7) . . . . ? C8 C13 C14 O4 -174.3(4) . . . . ? C12 C13 C14 O3 -169.7(4) . . . . ? C8 C13 C14 O3 8.7(6) . . . . ? C19 N4 C15 C16 -0.6(7) . . . . ? Zn1 N4 C15 C16 171.2(4) . . . . ? N4 C15 C16 C17 -0.5(8) . . . . ? C15 C16 C17 C18 1.6(8) . . . . ? C16 C17 C18 C19 -1.7(8) . . . . ? C15 N4 C19 C18 0.5(7) . . . . ? Zn1 N4 C19 C18 -170.9(4) . . . . ? C17 C18 C19 N4 0.6(8) . . . . ? C24 N3 C20 C21 1.3(7) . . . . ? Zn1 N3 C20 C21 -179.7(4) . . . . ? N3 C20 C21 C22 -1.2(9) . . . . ? C20 C21 C22 C23 0.7(9) . . . . ? C21 C22 C23 C24 -0.5(10) . . . . ? C20 N3 C24 C23 -1.0(8) . . . . ? Zn1 N3 C24 C23 -179.9(4) . . . . ? C22 C23 C24 N3 0.6(9) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.341 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.072 # Attachment 'Compound 4.CIF' data_tyz-027 _database_code_depnum_ccdc_archive 'CCDC 651801' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cd N2 O6' _chemical_formula_weight 416.66 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.5357(8) _cell_length_b 24.334(3) _cell_length_c 6.0750(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.127(2) _cell_angle_gamma 90.00 _cell_volume 734.72(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1320 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 25.06 _exptl_crystal_description prism _exptl_crystal_colour Red _exptl_crystal_size_max .26 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 1.520 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min .4310 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens SMART CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 2393 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.06 _reflns_number_total 1325 _reflns_number_gt 1174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _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^)+(0.0979P)^2^+11.5870P] 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 0.046(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1325 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0933 _refine_ls_wR_factor_ref 0.2537 _refine_ls_wR_factor_gt 0.2446 _refine_ls_goodness_of_fit_ref 1.289 _refine_ls_restrained_S_all 1.289 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.006 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 Cd Cd 0.3761(3) 0.2500 0.5173(2) 0.0367(7) Uani 1 2 d S . . OW1 O -0.048(3) 0.2500 0.202(3) 0.059(4) Uani 1 2 d S . . OW2 O 0.275(3) 0.2500 0.839(3) 0.063(4) Uani 1 2 d S . . O1 O 0.515(2) 0.3170(5) 0.3181(19) 0.054(3) Uani 1 1 d . . . O2 O 0.733(2) 0.3166(4) 0.7183(19) 0.052(3) Uani 1 1 d . . . C1 C 0.700(3) 0.3339(5) 0.517(2) 0.037(3) Uani 1 1 d . . . C2 C 0.883(3) 0.3774(5) 0.496(2) 0.036(3) Uani 1 1 d . . . C3 C 1.100(3) 0.3961(6) 0.706(3) 0.050(4) Uani 1 1 d . . . H3A H 1.1275 0.3823 0.8577 0.060 Uiso 1 1 calc R . . C4 C 1.277(3) 0.4353(7) 0.692(3) 0.061(4) Uani 1 1 d . . . H4A H 1.4203 0.4482 0.8330 0.073 Uiso 1 1 calc R . . C5 C 1.235(3) 0.4549(6) 0.458(3) 0.052(4) Uani 1 1 d . . . C6 C 1.021(4) 0.4363(7) 0.258(3) 0.056(4) Uani 1 1 d . . . H6A H 0.9876 0.4504 0.1048 0.068 Uiso 1 1 calc R . . C7 C 0.850(3) 0.3968(6) 0.274(3) 0.050(4) Uani 1 1 d . . . H7A H 0.7098 0.3833 0.1313 0.060 Uiso 1 1 calc R . . N N 1.405(3) 0.4955(6) 0.407(3) 0.064(4) 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 Cd 0.0401(9) 0.0407(10) 0.0323(9) 0.000 0.0189(6) 0.000 OW1 0.046(8) 0.067(11) 0.053(9) 0.000 0.010(7) 0.000 OW2 0.047(9) 0.080(12) 0.063(11) 0.000 0.025(8) 0.000 O1 0.065(6) 0.062(7) 0.040(6) -0.009(5) 0.027(5) -0.020(6) O2 0.061(6) 0.051(6) 0.042(6) 0.013(5) 0.020(5) -0.011(5) C1 0.050(8) 0.026(6) 0.037(8) -0.003(5) 0.020(6) -0.001(5) C2 0.048(7) 0.030(6) 0.031(7) -0.006(5) 0.017(6) -0.006(6) C3 0.062(9) 0.043(8) 0.039(8) 0.008(7) 0.016(7) -0.005(7) C4 0.057(9) 0.043(9) 0.063(11) -0.002(8) 0.010(8) -0.015(8) C5 0.056(9) 0.030(7) 0.084(12) 0.005(8) 0.042(9) -0.005(7) C6 0.080(11) 0.050(9) 0.051(9) 0.002(8) 0.039(9) -0.017(8) C7 0.068(10) 0.043(8) 0.031(7) 0.002(6) 0.015(7) -0.004(7) N 0.088(11) 0.054(8) 0.047(8) 0.002(7) 0.026(7) 0.005(8) _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 Cd OW2 2.259(17) . ? Cd OW1 2.284(15) . ? Cd O1 2.352(10) 4_565 ? Cd O1 2.352(11) . ? Cd O2 2.429(10) . ? Cd O2 2.429(10) 4_565 ? Cd C1 2.718(13) . ? Cd C1 2.718(13) 4_565 ? O1 C1 1.260(17) . ? O2 C1 1.229(16) . ? C1 C2 1.510(18) . ? C2 C7 1.362(19) . ? C2 C3 1.386(19) . ? C3 C4 1.40(2) . ? C4 C5 1.42(2) . ? C5 C6 1.35(2) . ? C5 N 1.49(2) . ? C6 C7 1.38(2) . ? N N 1.18(3) 3_866 ? 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 OW2 Cd OW1 99.9(6) . . ? OW2 Cd O1 135.0(3) . 4_565 ? OW1 Cd O1 90.9(4) . 4_565 ? OW2 Cd O1 135.0(3) . . ? OW1 Cd O1 90.9(4) . . ? O1 Cd O1 87.8(6) 4_565 . ? OW2 Cd O2 91.2(4) . . ? OW1 Cd O2 136.8(3) . . ? O1 Cd O2 110.1(4) 4_565 . ? O1 Cd O2 54.4(4) . . ? OW2 Cd O2 91.2(4) . 4_565 ? OW1 Cd O2 136.8(3) . 4_565 ? O1 Cd O2 54.4(4) 4_565 4_565 ? O1 Cd O2 110.1(4) . 4_565 ? O2 Cd O2 83.8(5) . 4_565 ? OW2 Cd C1 114.6(4) . . ? OW1 Cd C1 115.7(4) . . ? O1 Cd C1 98.9(4) 4_565 . ? O1 Cd C1 27.6(4) . . ? O2 Cd C1 26.9(4) . . ? O2 Cd C1 96.4(4) 4_565 . ? OW2 Cd C1 114.6(4) . 4_565 ? OW1 Cd C1 115.7(4) . 4_565 ? O1 Cd C1 27.6(4) 4_565 4_565 ? O1 Cd C1 98.9(4) . 4_565 ? O2 Cd C1 96.4(4) . 4_565 ? O2 Cd C1 26.9(4) 4_565 4_565 ? C1 Cd C1 97.3(6) . 4_565 ? C1 O1 Cd 92.6(8) . . ? C1 O2 Cd 89.8(8) . . ? O2 C1 O1 122.9(13) . . ? O2 C1 C2 120.8(12) . . ? O1 C1 C2 116.2(12) . . ? O2 C1 Cd 63.3(7) . . ? O1 C1 Cd 59.8(7) . . ? C2 C1 Cd 174.2(9) . . ? C7 C2 C3 118.9(13) . . ? C7 C2 C1 121.5(12) . . ? C3 C2 C1 119.6(12) . . ? C2 C3 C4 120.9(14) . . ? C3 C4 C5 118.7(14) . . ? C6 C5 C4 119.0(13) . . ? C6 C5 N 114.8(15) . . ? C4 C5 N 126.3(15) . . ? C5 C6 C7 121.8(15) . . ? C2 C7 C6 120.7(14) . . ? N N C5 107.5(19) 3_866 . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.426 _refine_diff_density_min -1.440 _refine_diff_density_rms 0.283 data_xb1125m _database_code_depnum_ccdc_archive 'CCDC 651802' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Co N6 O6' _chemical_formula_weight 679.59 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' Co Co 0.3494 0.9721 '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 6.0885(13) _cell_length_b 9.586(2) _cell_length_c 13.926(3) _cell_angle_alpha 92.253(4) _cell_angle_beta 90.182(4) _cell_angle_gamma 102.491(4) _cell_volume 792.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 287 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 15.84 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 353 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7708 _exptl_absorpt_correction_T_max 0.9001 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 4021 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.1543 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2754 _reflns_number_gt 1374 _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^)+(0.0220P)^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 SHELXL _refine_ls_extinction_coef 0.0081(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2754 _refine_ls_number_parameters 221 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1298 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 0.0000 0.0000 0.0337(3) Uani 1 2 d S . . N1 N 0.0934(6) 0.5198(5) 0.4852(3) 0.0668(13) Uani 1 1 d . . . N2 N -0.0202(6) -0.2120(3) 0.0494(2) 0.0367(9) Uani 1 1 d . . . N3 N 0.6524(9) 0.8810(5) 0.2579(3) 0.0707(13) Uani 1 1 d . . . O1 O 0.1634(5) 0.0750(3) 0.12945(19) 0.0479(9) Uani 1 1 d . . . O2 O 0.5101(5) 0.2155(3) 0.1347(2) 0.0511(9) Uani 1 1 d . . . O3 O 0.3044(5) 0.0023(3) -0.0703(2) 0.0429(8) Uani 1 1 d D . . C1 C 0.3131(8) 0.1783(5) 0.1641(3) 0.0383(11) Uani 1 1 d . . . C2 C 0.2477(7) 0.2603(4) 0.2495(3) 0.0323(10) Uani 1 1 d . . . C3 C 0.0298(7) 0.2295(5) 0.2850(3) 0.0468(12) Uani 1 1 d . . . H3 H -0.0775 0.1550 0.2568 0.056 Uiso 1 1 calc R . . C4 C -0.0277(8) 0.3095(5) 0.3623(3) 0.0545(14) Uani 1 1 d . . . H4 H -0.1722 0.2865 0.3870 0.065 Uiso 1 1 calc R . . C5 C 0.1277(9) 0.4226(5) 0.4026(3) 0.0482(13) Uani 1 1 d . . . C6 C 0.3431(8) 0.4544(5) 0.3688(3) 0.0581(14) Uani 1 1 d . . . H6 H 0.4492 0.5294 0.3972 0.070 Uiso 1 1 calc R . . C7 C 0.4017(7) 0.3743(5) 0.2923(3) 0.0469(12) Uani 1 1 d . . . H7 H 0.5474 0.3973 0.2689 0.056 Uiso 1 1 calc R . . C8 C 0.1623(7) -0.2483(5) 0.0897(3) 0.0465(12) Uani 1 1 d . . . H8 H 0.2991 -0.1823 0.0898 0.056 Uiso 1 1 calc R . . C9 C 0.1544(8) -0.3773(6) 0.1300(3) 0.0546(14) Uani 1 1 d . . . H9 H 0.2823 -0.3971 0.1583 0.065 Uiso 1 1 calc R . . C10 C -0.0453(9) -0.4769(5) 0.1281(3) 0.0567(14) Uani 1 1 d . . . H10 H -0.0536 -0.5657 0.1542 0.068 Uiso 1 1 calc R . . C11 C -0.2329(8) -0.4441(5) 0.0872(3) 0.0519(13) Uani 1 1 d . . . H11 H -0.3702 -0.5096 0.0855 0.062 Uiso 1 1 calc R . . C12 C -0.2120(7) -0.3119(5) 0.0488(3) 0.0422(12) Uani 1 1 d . . . H12 H -0.3388 -0.2904 0.0206 0.051 Uiso 1 1 calc R . . C13 C 0.8162(10) 0.8333(6) 0.3003(5) 0.0804(18) Uani 1 1 d . . . H13 H 0.9368 0.8187 0.2634 0.096 Uiso 1 1 calc R . . C14 C 0.8153(11) 0.8047(6) 0.3959(5) 0.0822(18) Uani 1 1 d . . . H14 H 0.9328 0.7713 0.4232 0.099 Uiso 1 1 calc R . . C15 C 0.6397(13) 0.8260(6) 0.4502(4) 0.0858(19) Uani 1 1 d . . . H15 H 0.6364 0.8086 0.5154 0.103 Uiso 1 1 calc R . . C16 C 0.4687(11) 0.8731(6) 0.4084(5) 0.0809(18) Uani 1 1 d . . . H16 H 0.3454 0.8868 0.4439 0.097 Uiso 1 1 calc R . . C17 C 0.4837(9) 0.8996(5) 0.3128(4) 0.0669(15) Uani 1 1 d . . . H17 H 0.3675 0.9330 0.2845 0.080 Uiso 1 1 calc R . . H3A H 0.354(7) -0.073(3) -0.079(3) 0.080 Uiso 1 1 d D . . H3B H 0.311(8) 0.037(5) -0.1256(15) 0.080 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 Co1 0.0333(6) 0.0329(6) 0.0356(6) -0.0011(4) 0.0050(4) 0.0092(4) N1 0.064(4) 0.072(3) 0.066(3) 0.011(2) 0.008(3) 0.017(3) N2 0.033(2) 0.039(2) 0.037(2) -0.0038(18) 0.004(2) 0.006(2) N3 0.071(3) 0.089(4) 0.055(3) 0.010(2) 0.011(3) 0.023(3) O1 0.053(2) 0.046(2) 0.039(2) -0.0110(15) 0.0028(16) 0.0021(16) O2 0.046(2) 0.056(2) 0.052(2) -0.0086(16) 0.0154(17) 0.0125(17) O3 0.0421(18) 0.041(2) 0.051(2) 0.0042(17) 0.0158(17) 0.0190(15) C1 0.053(3) 0.040(3) 0.027(3) 0.006(2) 0.005(3) 0.022(3) C2 0.042(3) 0.034(3) 0.024(3) -0.002(2) -0.001(2) 0.016(2) C3 0.049(3) 0.047(3) 0.046(3) 0.002(2) 0.004(3) 0.014(2) C4 0.054(3) 0.074(4) 0.044(3) 0.008(3) 0.023(3) 0.031(3) C5 0.076(4) 0.049(3) 0.029(3) -0.010(2) 0.001(3) 0.035(3) C6 0.061(4) 0.062(3) 0.048(3) -0.016(3) 0.008(3) 0.011(3) C7 0.053(3) 0.048(3) 0.040(3) -0.008(2) 0.003(2) 0.014(3) C8 0.043(3) 0.045(3) 0.052(3) -0.002(3) -0.001(3) 0.012(3) C9 0.060(4) 0.059(4) 0.054(3) 0.011(3) 0.000(3) 0.031(3) C10 0.076(4) 0.041(3) 0.058(4) 0.015(3) 0.013(3) 0.020(3) C11 0.053(3) 0.041(3) 0.059(4) 0.008(3) 0.001(3) 0.003(3) C12 0.044(3) 0.035(3) 0.047(3) 0.000(2) 0.001(2) 0.008(2) C13 0.076(5) 0.101(5) 0.072(5) 0.012(4) 0.016(4) 0.036(4) C14 0.101(5) 0.093(5) 0.066(5) 0.022(4) 0.001(4) 0.048(4) C15 0.119(6) 0.088(5) 0.050(4) 0.013(3) 0.016(4) 0.021(4) C16 0.086(5) 0.096(5) 0.066(5) 0.001(4) 0.014(4) 0.032(4) C17 0.066(4) 0.066(4) 0.068(4) 0.003(3) -0.004(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.082(3) . ? Co1 O1 2.082(3) 2 ? Co1 O3 2.095(3) 2 ? Co1 O3 2.095(3) . ? Co1 N2 2.150(3) . ? Co1 N2 2.150(3) 2 ? N1 N1 1.198(6) 2_566 ? N1 C5 1.495(6) . ? N2 C12 1.340(4) . ? N2 C8 1.360(5) . ? N3 C17 1.321(5) . ? N3 C13 1.329(6) . ? O1 C1 1.270(4) . ? O2 C1 1.250(5) . ? O3 H3A 0.846(10) . ? O3 H3B 0.849(10) . ? C1 C2 1.503(5) . ? C2 C7 1.390(5) . ? C2 C3 1.392(5) . ? C3 C4 1.387(5) . ? C3 H3 0.9300 . ? C4 C5 1.376(6) . ? C4 H4 0.9300 . ? C5 C6 1.370(6) . ? C6 C7 1.381(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.370(5) . ? C8 H8 0.9300 . ? C9 C10 1.373(6) . ? C9 H9 0.9300 . ? C10 C11 1.376(6) . ? C10 H10 0.9300 . ? C11 C12 1.376(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.370(6) . ? C13 H13 0.9300 . ? C14 C15 1.358(7) . ? C14 H14 0.9300 . ? C15 C16 1.358(7) . ? C15 H15 0.9300 . ? C16 C17 1.365(6) . ? C16 H16 0.9300 . ? C17 H17 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 O1 Co1 O1 180.0 . 2 ? O1 Co1 O3 87.63(11) . 2 ? O1 Co1 O3 92.37(11) 2 2 ? O1 Co1 O3 92.37(11) . . ? O1 Co1 O3 87.63(11) 2 . ? O3 Co1 O3 180.0 2 . ? O1 Co1 N2 86.97(12) . . ? O1 Co1 N2 93.03(12) 2 . ? O3 Co1 N2 87.26(12) 2 . ? O3 Co1 N2 92.74(12) . . ? O1 Co1 N2 93.03(12) . 2 ? O1 Co1 N2 86.97(12) 2 2 ? O3 Co1 N2 92.74(12) 2 2 ? O3 Co1 N2 87.26(12) . 2 ? N2 Co1 N2 180.0 . 2 ? N1 N1 C5 108.7(6) 2_566 . ? C12 N2 C8 116.2(4) . . ? C12 N2 Co1 123.0(3) . . ? C8 N2 Co1 120.6(3) . . ? C17 N3 C13 116.6(5) . . ? C1 O1 Co1 140.6(3) . . ? Co1 O3 H3A 121(3) . . ? Co1 O3 H3B 114(3) . . ? H3A O3 H3B 104(4) . . ? O2 C1 O1 125.9(4) . . ? O2 C1 C2 117.5(4) . . ? O1 C1 C2 116.6(4) . . ? C7 C2 C3 118.1(4) . . ? C7 C2 C1 120.4(4) . . ? C3 C2 C1 121.3(4) . . ? C4 C3 C2 120.2(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 120.2(4) . . ? C6 C5 N1 112.5(4) . . ? C4 C5 N1 127.3(4) . . ? C5 C6 C7 119.6(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C2 121.5(4) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? N2 C8 C9 123.1(4) . . ? N2 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? C8 C9 C10 118.9(4) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 119.4(5) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 118.2(4) . . ? C12 C11 H11 120.9 . . ? C10 C11 H11 120.9 . . ? N2 C12 C11 124.0(4) . . ? N2 C12 H12 118.0 . . ? C11 C12 H12 118.0 . . ? N3 C13 C14 123.0(5) . . ? N3 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C15 C14 C13 118.7(6) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C16 C15 C14 119.5(6) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 117.9(6) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? N3 C17 C16 124.3(5) . . ? N3 C17 H17 117.9 . . ? C16 C17 H17 117.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Co1 N2 C12 129.5(3) . . . . ? O1 Co1 N2 C12 -50.5(3) 2 . . . ? O3 Co1 N2 C12 41.7(3) 2 . . . ? O3 Co1 N2 C12 -138.3(3) . . . . ? N2 Co1 N2 C12 -68(4) 2 . . . ? O1 Co1 N2 C8 -45.9(3) . . . . ? O1 Co1 N2 C8 134.1(3) 2 . . . ? O3 Co1 N2 C8 -133.7(3) 2 . . . ? O3 Co1 N2 C8 46.3(3) . . . . ? N2 Co1 N2 C8 116(4) 2 . . . ? O1 Co1 O1 C1 -1.9(11) 2 . . . ? O3 Co1 O1 C1 -124.7(4) 2 . . . ? O3 Co1 O1 C1 55.3(4) . . . . ? N2 Co1 O1 C1 147.9(4) . . . . ? N2 Co1 O1 C1 -32.1(4) 2 . . . ? Co1 O1 C1 O2 -56.0(6) . . . . ? Co1 O1 C1 C2 125.6(4) . . . . ? O2 C1 C2 C7 1.0(6) . . . . ? O1 C1 C2 C7 179.6(4) . . . . ? O2 C1 C2 C3 177.7(4) . . . . ? O1 C1 C2 C3 -3.7(6) . . . . ? C7 C2 C3 C4 -1.4(6) . . . . ? C1 C2 C3 C4 -178.2(4) . . . . ? C2 C3 C4 C5 2.0(7) . . . . ? C3 C4 C5 C6 -2.2(7) . . . . ? C3 C4 C5 N1 179.6(4) . . . . ? N1 N1 C5 C6 -175.6(5) 2_566 . . . ? N1 N1 C5 C4 2.7(8) 2_566 . . . ? C4 C5 C6 C7 1.7(7) . . . . ? N1 C5 C6 C7 -179.9(4) . . . . ? C5 C6 C7 C2 -1.1(7) . . . . ? C3 C2 C7 C6 0.9(6) . . . . ? C1 C2 C7 C6 177.7(4) . . . . ? C12 N2 C8 C9 -1.6(6) . . . . ? Co1 N2 C8 C9 174.1(3) . . . . ? N2 C8 C9 C10 1.6(7) . . . . ? C8 C9 C10 C11 -1.0(7) . . . . ? C9 C10 C11 C12 0.5(7) . . . . ? C8 N2 C12 C11 1.1(6) . . . . ? Co1 N2 C12 C11 -174.5(3) . . . . ? C10 C11 C12 N2 -0.6(7) . . . . ? C17 N3 C13 C14 -0.3(8) . . . . ? N3 C13 C14 C15 -0.1(9) . . . . ? C13 C14 C15 C16 0.9(9) . . . . ? C14 C15 C16 C17 -1.2(9) . . . . ? C13 N3 C17 C16 -0.1(8) . . . . ? C15 C16 C17 N3 0.8(8) . . . . ? 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 O3 H3B N3 0.849(10) 2.025(12) 2.872(5) 176(5) 2_665 O3 H3A O2 0.846(10) 1.888(17) 2.705(4) 162(4) 2_655 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.385 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.074 # Attachment 'Compound 6.cif' data_tyh437m _database_code_depnum_ccdc_archive 'CCDC 651803' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O5 Zn' _chemical_formula_weight 379.66 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 9.7462(17) _cell_length_b 19.627(3) _cell_length_c 10.3287(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.361(3) _cell_angle_gamma 90.00 _cell_volume 1943.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.64 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 1.287 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.4792 _exptl_absorpt_correction_T_max 0.6987 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _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 'Bruker Noniu 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 4704 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1766 _reflns_number_gt 1583 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1818P)^2^+5.4491P] 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 1766 _refine_ls_number_parameters 123 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.2513 _refine_ls_wR_factor_gt 0.2358 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 0.57638(9) 0.0000 0.88728(7) 0.0478(5) Uani 1 2 d S . . O1 O 0.6851(6) 0.0724(3) 1.0044(5) 0.0822(15) Uani 1 1 d . . . O2 O 0.5719(6) 0.0720(3) 1.1744(5) 0.0751(14) Uani 1 1 d . . . O3 O 0.6862(11) 0.0000 0.7354(8) 0.112(3) Uani 1 2 d SD . . H3B H 0.7746 0.0000 0.7567 0.134 Uiso 0.50 2 d SPR A 1 H3C H 0.6756 0.0324 0.6799 0.134 Uiso 0.25 1 d PR A 2 N1A N 0.817(2) 0.2528(14) 1.483(2) 0.084(6) Uani 0.50 1 d P . 3 C1A C 0.8727(18) 0.1712(9) 1.1202(16) 0.071(4) Uiso 0.50 1 d P B 3 H1A H 0.8961 0.1483 1.0484 0.086 Uiso 0.50 1 calc PR B 3 C2A C 0.953(2) 0.2247(10) 1.177(2) 0.091(5) Uiso 0.50 1 d P B 3 H2A H 1.0211 0.2441 1.1364 0.109 Uiso 0.50 1 calc PR B 3 C3A C 0.928(2) 0.2496(11) 1.302(2) 0.089(5) Uiso 0.50 1 d P B 3 H3A H 0.9815 0.2857 1.3424 0.107 Uiso 0.50 1 calc PR B 3 C4A C 0.8293(16) 0.2214(8) 1.3618(15) 0.066(3) Uiso 0.50 1 d P B 3 N1B N 0.763(3) 0.2770(13) 1.460(3) 0.091(7) Uani 0.50 1 d P . 4 C1B C 0.8193(16) 0.1947(8) 1.0940(16) 0.069(3) Uiso 0.50 1 d P B 4 H1B H 0.8185 0.1827 1.0067 0.082 Uiso 0.50 1 calc PR B 4 C2B C 0.887(2) 0.2534(11) 1.142(2) 0.091(5) Uiso 0.50 1 d P B 4 H2B H 0.9448 0.2760 1.0947 0.109 Uiso 0.50 1 calc PR B 4 C3B C 0.867(2) 0.2787(10) 1.264(2) 0.090(5) Uiso 0.50 1 d P B 4 H3B' H 0.9136 0.3178 1.2986 0.108 Uiso 0.50 1 calc PR B 4 C4 C 0.7801(16) 0.2466(9) 1.3317(15) 0.069(3) Uiso 0.50 1 d P B 4 C5 C 0.7304(9) 0.1763(5) 1.2950(8) 0.095(3) Uani 1 1 d . . . H5A H 0.6532 0.1634 1.3308 0.114 Uiso 1 1 calc R B 3 C6 C 0.7498(9) 0.1511(5) 1.1742(7) 0.086(2) Uani 1 1 d . B . C7 C 0.6616(8) 0.0939(3) 1.1138(6) 0.0648(16) Uani 1 1 d . . . C8A C 0.622(3) 0.0000 0.5963(14) 0.107(8) Uiso 0.50 2 d SPD C 1 H8AA H 0.5626 0.0393 0.5796 0.128 Uiso 0.25 1 d PR C 1 H8AB H 0.5625 -0.0393 0.5797 0.128 Uiso 0.25 1 d PR C 1 C9A C 0.735(4) 0.0000 0.510(4) 0.135(12) Uiso 0.50 2 d SPD C 1 H9AA H 0.6795 0.0000 0.4226 0.203 Uiso 0.50 2 d SPR C 1 H9AB H 0.7925 0.0399 0.5210 0.203 Uiso 0.25 1 d PR C 1 H9AC H 0.7927 -0.0398 0.5205 0.203 Uiso 0.25 1 d PR C 1 C8B C 0.776(7) -0.050(3) 0.683(5) 0.20(3) Uiso 0.25 1 d PD . 2 H8BA H 0.7393 -0.0942 0.6990 0.238 Uiso 0.25 1 d PR . 2 H8BB H 0.8594 -0.0416 0.7461 0.238 Uiso 0.25 1 d PR . 2 C9B C 0.807(4) -0.0383(19) 0.543(4) 0.091(9) Uiso 0.25 1 d PD . 2 H9BA H 0.8749 -0.0714 0.5270 0.137 Uiso 0.25 1 d PR . 2 H9BB H 0.7212 -0.0458 0.4829 0.137 Uiso 0.25 1 d PR . 2 H9BC H 0.8411 0.0115 0.5299 0.137 Uiso 0.25 1 d PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0716(7) 0.0447(6) 0.0294(6) 0.000 0.0152(4) 0.000 O1 0.114(4) 0.077(3) 0.056(3) -0.028(2) 0.016(3) -0.029(3) O2 0.094(3) 0.069(3) 0.063(3) -0.021(2) 0.015(2) -0.027(3) O3 0.119(7) 0.168(10) 0.053(4) 0.000 0.030(4) 0.000 N1A 0.069(14) 0.114(17) 0.073(11) -0.045(12) 0.023(9) -0.018(10) N1B 0.076(14) 0.110(16) 0.089(14) -0.059(12) 0.019(11) -0.020(11) C5 0.106(5) 0.127(7) 0.057(4) -0.041(5) 0.028(4) -0.054(5) C6 0.117(6) 0.094(5) 0.052(4) -0.027(4) 0.029(4) -0.043(5) C7 0.089(4) 0.060(4) 0.043(3) -0.008(3) 0.007(3) -0.015(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.036(5) . ? Zn1 O1 2.036(4) 6 ? Zn1 O2 2.039(5) 5_657 ? Zn1 O2 2.039(5) 2_657 ? Zn1 O3 2.052(9) . ? Zn1 Zn1 2.9809(16) 5_657 ? O1 C7 1.265(8) . ? O2 C7 1.240(8) . ? O2 Zn1 2.039(5) 5_657 ? O3 C8A 1.462(10) . ? O3 C8B 1.486(10) 6 ? O3 C8B 1.486(10) . ? N1A N1A 1.41(4) 7_658 ? N1A C4A 1.42(3) . ? C1A C2A 1.38(2) . ? C1A C6 1.464(18) . ? C2A C3A 1.44(3) . ? C3A C4A 1.36(3) . ? C4A C5 1.397(16) . ? N1B N1B 1.40(6) 7_658 ? N1B C4 1.49(3) . ? C1B C2B 1.37(2) . ? C1B C6 1.442(17) . ? C2B C3B 1.40(3) . ? C3B C4 1.34(2) . ? C4 C5 1.490(18) . ? C5 C6 1.387(10) . ? C6 C7 1.481(9) . ? C8A C9A 1.539(10) . ? C8B C9B 1.547(10) . ? C8B C8B 1.97(10) 6 ? C9B C9B 1.51(8) 6 ? 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 O1 88.6(4) . 6 ? O1 Zn1 O2 158.9(3) . 5_657 ? O1 Zn1 O2 88.0(3) 6 5_657 ? O1 Zn1 O2 88.0(3) . 2_657 ? O1 Zn1 O2 158.9(3) 6 2_657 ? O2 Zn1 O2 87.7(3) 5_657 2_657 ? O1 Zn1 O3 99.6(3) . . ? O1 Zn1 O3 99.6(3) 6 . ? O2 Zn1 O3 101.5(3) 5_657 . ? O2 Zn1 O3 101.5(2) 2_657 . ? O1 Zn1 Zn1 79.36(16) . 5_657 ? O1 Zn1 Zn1 79.36(16) 6 5_657 ? O2 Zn1 Zn1 79.56(15) 5_657 5_657 ? O2 Zn1 Zn1 79.56(15) 2_657 5_657 ? O3 Zn1 Zn1 178.6(3) . 5_657 ? C7 O1 Zn1 127.2(5) . . ? C7 O2 Zn1 127.4(4) . 5_657 ? C8A O3 C8B 80(2) . 6 ? C8A O3 C8B 80(2) . . ? C8B O3 C8B 83(5) 6 . ? C8A O3 Zn1 124.1(13) . . ? C8B O3 Zn1 134.6(18) 6 . ? C8B O3 Zn1 134.6(18) . . ? N1A N1A C4A 115(2) 7_658 . ? C2A C1A C6 118.9(15) . . ? C1A C2A C3A 118.0(18) . . ? C4A C3A C2A 121.1(18) . . ? C3A C4A C5 121.3(15) . . ? C3A C4A N1A 113.9(17) . . ? C5 C4A N1A 123.4(15) . . ? N1B N1B C4 107(2) 7_658 . ? C2B C1B C6 122.0(15) . . ? C1B C2B C3B 119.4(19) . . ? C4 C3B C2B 120.1(19) . . ? C3B C4 N1B 117.1(18) . . ? C3B C4 C5 120.5(14) . . ? N1B C4 C5 120.9(16) . . ? C6 C5 C4A 118.5(9) . . ? C6 C5 C4 118.0(9) . . ? C4A C5 C4 28.7(7) . . ? C5 C6 C1B 117.4(9) . . ? C5 C6 C1A 120.0(9) . . ? C1B C6 C1A 28.3(7) . . ? C5 C6 C7 119.1(7) . . ? C1B C6 C7 120.3(8) . . ? C1A C6 C7 119.8(9) . . ? O2 C7 O1 126.3(6) . . ? O2 C7 C6 117.3(6) . . ? O1 C7 C6 116.3(6) . . ? O3 C8A C9A 110(2) . . ? O3 C8B C9B 118(3) . . ? O3 C8B C8B 48(3) . 6 ? C9B C8B C8B 81(2) . 6 ? C9B C9B C8B 99(2) 6 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.200 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.146 # Attachment 'Compound 7.CIF' data_f176 _database_code_depnum_ccdc_archive 'CCDC 651804' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H38 Co3 N8 O12' _chemical_formula_weight 1191.73 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3958(13) _cell_length_b 11.3170(15) _cell_length_c 11.5539(15) _cell_angle_alpha 91.235(3) _cell_angle_beta 92.032(3) _cell_angle_gamma 113.549(3) _cell_volume 1244.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2862 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description PRISM _exptl_crystal_colour violet _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 607 _exptl_absorpt_coefficient_mu 1.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6878 _exptl_absorpt_correction_T_max 0.8153 _exptl_absorpt_process_details 'Sadabs; SHELDRICK 1996' _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 'Bruker 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 8589 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0982 _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 -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.57 _reflns_number_total 5699 _reflns_number_gt 3244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5699 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.65353(5) 0.01422(5) 0.26804(5) 0.03382(17) Uani 1 1 d . . . Co2 Co 0.5000 0.0000 0.0000 0.02950(19) Uani 1 2 d S . . O1 O 0.5834(3) 0.1573(3) 0.2754(2) 0.0446(7) Uani 1 1 d . . . O2 O 0.5565(3) 0.1815(2) 0.0859(2) 0.0449(7) Uani 1 1 d . . . O3 O 0.4681(3) -0.1367(3) 0.2878(2) 0.0418(7) Uani 1 1 d . . . O4 O 0.3661(3) -0.0988(3) 0.1272(2) 0.0437(7) Uani 1 1 d . . . O5 O 0.6647(3) -0.0205(3) 0.0919(2) 0.0418(7) Uani 1 1 d . . . O6 O 0.7751(4) -0.1165(3) 0.1866(3) 0.0764(11) Uani 1 1 d . . . N1 N 0.7355(3) 0.0213(3) 0.4380(3) 0.0369(8) Uani 1 1 d . . . N2 N 0.8621(3) 0.1629(3) 0.2611(3) 0.0404(8) Uani 1 1 d . . . N3 N 0.5095(4) 0.5400(3) 0.4628(3) 0.0474(9) Uani 1 1 d . . . N4 N 0.0611(3) -0.4617(3) 0.4893(3) 0.0520(10) Uani 1 1 d . . . C1 C 0.6704(5) -0.0464(4) 0.5263(4) 0.0458(11) Uani 1 1 d . . . H1 H 0.5754 -0.0995 0.5161 0.055 Uiso 1 1 calc R . . C2 C 0.7382(5) -0.0418(5) 0.6341(4) 0.0573(13) Uani 1 1 d . . . H2 H 0.6895 -0.0915 0.6940 0.069 Uiso 1 1 calc R . . C3 C 0.8759(5) 0.0364(5) 0.6494(4) 0.0531(12) Uani 1 1 d . . . H3 H 0.9226 0.0401 0.7204 0.064 Uiso 1 1 calc R . . C4 C 0.9485(5) 0.1113(4) 0.5605(4) 0.0450(11) Uani 1 1 d . . . C5 C 1.0937(5) 0.1966(5) 0.5691(5) 0.0579(13) Uani 1 1 d . . . H5 H 1.1452 0.2042 0.6384 0.069 Uiso 1 1 calc R . . C6 C 1.1565(5) 0.2651(5) 0.4801(5) 0.0660(15) Uani 1 1 d . . . H6 H 1.2516 0.3184 0.4884 0.079 Uiso 1 1 calc R . . C7 C 1.0831(4) 0.2597(4) 0.3724(4) 0.0472(11) Uani 1 1 d . . . C8 C 1.1430(5) 0.3311(5) 0.2761(5) 0.0623(14) Uani 1 1 d . . . H8 H 1.2372 0.3874 0.2800 0.075 Uiso 1 1 calc R . . C9 C 1.0629(5) 0.3179(5) 0.1770(5) 0.0657(14) Uani 1 1 d . . . H9 H 1.1016 0.3649 0.1127 0.079 Uiso 1 1 calc R . . C10 C 0.9216(5) 0.2324(4) 0.1735(4) 0.0531(12) Uani 1 1 d . . . H10 H 0.8672 0.2245 0.1058 0.064 Uiso 1 1 calc R . . C11 C 0.9411(4) 0.1761(4) 0.3605(4) 0.0374(10) Uani 1 1 d . . . C12 C 0.8728(4) 0.1007(4) 0.4553(4) 0.0356(9) Uani 1 1 d . . . C13 C 0.5688(4) 0.2189(4) 0.1898(4) 0.0362(9) Uani 1 1 d . . . C14 C 0.5641(4) 0.3475(4) 0.2165(3) 0.0350(9) Uani 1 1 d . . . C15 C 0.5808(5) 0.4333(4) 0.1295(4) 0.0555(12) Uani 1 1 d . . . H15 H 0.5949 0.4113 0.0544 0.067 Uiso 1 1 calc R . . C16 C 0.5765(5) 0.5529(5) 0.1535(4) 0.0675(15) Uani 1 1 d . . . H16 H 0.5894 0.6112 0.0950 0.081 Uiso 1 1 calc R . . C17 C 0.5531(5) 0.5845(4) 0.2643(4) 0.0570(13) Uani 1 1 d . . . H17 H 0.5496 0.6640 0.2808 0.068 Uiso 1 1 calc R . . C18 C 0.5350(4) 0.4978(4) 0.3509(4) 0.0423(10) Uani 1 1 d . . . C19 C 0.5434(4) 0.3812(4) 0.3270(4) 0.0395(10) Uani 1 1 d . . . H19 H 0.5349 0.3248 0.3864 0.047 Uiso 1 1 calc R . . C20 C 0.3647(4) -0.1596(4) 0.2164(4) 0.0376(9) Uani 1 1 d . . . C21 C 0.2260(4) -0.2637(4) 0.2442(4) 0.0399(10) Uani 1 1 d . . . C22 C 0.1141(5) -0.2980(5) 0.1653(4) 0.0645(14) Uani 1 1 d . . . H22 H 0.1264 -0.2595 0.0939 0.077 Uiso 1 1 calc R . . C23 C -0.0165(5) -0.3889(6) 0.1900(5) 0.0824(18) Uani 1 1 d . . . H23 H -0.0900 -0.4119 0.1342 0.099 Uiso 1 1 calc R . . C24 C -0.0401(5) -0.4460(5) 0.2952(5) 0.0649(14) Uani 1 1 d . . . H24 H -0.1284 -0.5066 0.3116 0.078 Uiso 1 1 calc R . . C25 C 0.0715(4) -0.4109(4) 0.3759(4) 0.0439(10) Uani 1 1 d . . . C26 C 0.2036(4) -0.3212(4) 0.3501(4) 0.0391(10) Uani 1 1 d . . . H26 H 0.2779 -0.2997 0.4048 0.047 Uiso 1 1 calc R . . C27 C 0.7385(4) -0.0864(4) 0.0929(4) 0.0459(11) Uani 1 1 d . . . C28 C 0.7819(6) -0.1218(6) -0.0203(5) 0.0834(19) Uani 1 1 d . . . H28A H 0.8614 -0.1435 -0.0072 0.125 Uiso 1 1 calc R . . H28B H 0.8067 -0.0500 -0.0702 0.125 Uiso 1 1 calc R . . H28C H 0.7054 -0.1946 -0.0563 0.125 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0381(3) 0.0359(3) 0.0255(3) 0.0054(2) -0.0003(2) 0.0127(2) Co2 0.0354(4) 0.0294(4) 0.0211(4) 0.0043(3) 0.0036(3) 0.0099(3) O1 0.0598(18) 0.0427(16) 0.0387(17) 0.0022(14) -0.0009(15) 0.0283(15) O2 0.0626(19) 0.0352(15) 0.0346(17) -0.0022(13) 0.0019(15) 0.0175(14) O3 0.0388(15) 0.0429(16) 0.0395(17) 0.0154(14) 0.0045(14) 0.0111(13) O4 0.0437(16) 0.0493(17) 0.0335(16) 0.0174(14) 0.0110(14) 0.0124(14) O5 0.0425(15) 0.0506(17) 0.0365(17) -0.0006(14) -0.0004(13) 0.0234(14) O6 0.105(3) 0.070(2) 0.062(2) 0.004(2) -0.025(2) 0.045(2) N1 0.0440(19) 0.0417(19) 0.0298(19) 0.0024(16) -0.0005(16) 0.0225(16) N2 0.0433(19) 0.044(2) 0.0287(19) 0.0057(16) 0.0037(16) 0.0118(16) N3 0.052(2) 0.036(2) 0.048(3) -0.0047(16) -0.001(2) 0.0118(19) N4 0.052(2) 0.050(2) 0.044(2) 0.0180(19) 0.018(2) 0.0072(17) C1 0.050(3) 0.056(3) 0.035(2) 0.013(2) 0.004(2) 0.024(2) C2 0.075(3) 0.072(3) 0.036(3) 0.007(2) 0.006(3) 0.041(3) C3 0.067(3) 0.065(3) 0.039(3) 0.002(2) -0.009(2) 0.040(3) C4 0.051(3) 0.054(3) 0.038(3) -0.006(2) -0.008(2) 0.030(2) C5 0.053(3) 0.072(3) 0.054(3) -0.008(3) -0.016(3) 0.032(3) C6 0.042(3) 0.072(4) 0.073(4) -0.013(3) -0.017(3) 0.013(3) C7 0.036(2) 0.042(2) 0.061(3) -0.008(2) 0.002(2) 0.013(2) C8 0.035(2) 0.056(3) 0.082(4) 0.003(3) 0.013(3) 0.003(2) C9 0.063(3) 0.062(3) 0.064(4) 0.015(3) 0.025(3) 0.014(3) C10 0.055(3) 0.055(3) 0.039(3) 0.009(2) 0.004(2) 0.011(2) C11 0.037(2) 0.041(2) 0.037(2) -0.002(2) 0.0013(19) 0.0193(19) C12 0.037(2) 0.042(2) 0.032(2) -0.0047(19) -0.0051(19) 0.0216(19) C13 0.038(2) 0.032(2) 0.036(2) -0.0010(19) 0.0021(19) 0.0110(18) C14 0.039(2) 0.030(2) 0.032(2) -0.0005(18) -0.0027(18) 0.0106(17) C15 0.079(3) 0.043(3) 0.041(3) 0.000(2) 0.000(3) 0.021(2) C16 0.110(4) 0.048(3) 0.048(3) 0.010(2) -0.004(3) 0.035(3) C17 0.076(3) 0.036(2) 0.059(3) -0.001(2) -0.005(3) 0.024(2) C18 0.041(2) 0.035(2) 0.049(3) -0.007(2) -0.003(2) 0.0137(19) C19 0.040(2) 0.034(2) 0.043(3) 0.0031(19) -0.001(2) 0.0136(18) C20 0.047(2) 0.032(2) 0.036(2) 0.0089(19) 0.013(2) 0.0169(19) C21 0.039(2) 0.037(2) 0.037(2) 0.0106(19) 0.006(2) 0.0074(18) C22 0.054(3) 0.072(3) 0.046(3) 0.023(3) -0.001(2) 0.001(3) C23 0.056(3) 0.099(4) 0.052(3) 0.026(3) -0.008(3) -0.010(3) C24 0.043(3) 0.067(3) 0.060(3) 0.016(3) 0.005(3) -0.005(2) C25 0.045(2) 0.036(2) 0.047(3) 0.013(2) 0.014(2) 0.0096(19) C26 0.041(2) 0.034(2) 0.039(2) 0.0084(19) 0.005(2) 0.0126(19) C27 0.049(3) 0.045(3) 0.045(3) -0.003(2) -0.002(2) 0.021(2) C28 0.076(4) 0.119(5) 0.068(4) -0.025(4) 0.006(3) 0.054(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3 2.025(3) . ? Co1 O1 2.025(3) . ? Co1 O5 2.080(3) . ? Co1 N1 2.100(3) . ? Co1 N2 2.155(3) . ? Co2 O5 2.077(3) . ? Co2 O5 2.077(3) 2_655 ? Co2 O4 2.078(3) 2_655 ? Co2 O4 2.078(3) . ? Co2 O2 2.111(2) 2_655 ? Co2 O2 2.111(2) . ? O1 C13 1.261(5) . ? O2 C13 1.250(4) . ? O3 C20 1.268(5) . ? O4 C20 1.249(5) . ? O5 C27 1.265(5) . ? O6 C27 1.234(5) . ? N1 C1 1.325(5) . ? N1 C12 1.353(5) . ? N2 C10 1.309(5) . ? N2 C11 1.358(5) . ? N3 N3 1.224(7) 2_666 ? N3 C18 1.438(6) . ? N4 N4 1.256(6) 2_546 ? N4 C25 1.433(6) . ? C1 C2 1.398(6) . ? C1 H1 0.9300 . ? C2 C3 1.352(6) . ? C2 H2 0.9300 . ? C3 C4 1.387(6) . ? C3 H3 0.9300 . ? C4 C12 1.400(5) . ? C4 C5 1.429(6) . ? C5 C6 1.328(7) . ? C5 H5 0.9300 . ? C6 C7 1.424(7) . ? C6 H6 0.9300 . ? C7 C11 1.400(5) . ? C7 C8 1.401(7) . ? C8 C9 1.361(7) . ? C8 H8 0.9300 . ? C9 C10 1.398(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.429(6) . ? C13 C14 1.501(5) . ? C14 C19 1.374(5) . ? C14 C15 1.380(6) . ? C15 C16 1.395(6) . ? C15 H15 0.9300 . ? C16 C17 1.377(6) . ? C16 H16 0.9300 . ? C17 C18 1.381(6) . ? C17 H17 0.9300 . ? C18 C19 1.380(5) . ? C19 H19 0.9300 . ? C20 C21 1.504(5) . ? C21 C22 1.373(6) . ? C21 C26 1.381(6) . ? C22 C23 1.381(6) . ? C22 H22 0.9300 . ? C23 C24 1.372(7) . ? C23 H23 0.9300 . ? C24 C25 1.383(6) . ? C24 H24 0.9300 . ? C25 C26 1.390(5) . ? C26 H26 0.9300 . ? C27 C28 1.496(6) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Co1 O1 98.17(11) . . ? O3 Co1 O5 96.18(11) . . ? O1 Co1 O5 104.67(11) . . ? O3 Co1 N1 96.61(12) . . ? O1 Co1 N1 101.82(12) . . ? O5 Co1 N1 148.50(11) . . ? O3 Co1 N2 172.94(13) . . ? O1 Co1 N2 87.19(12) . . ? O5 Co1 N2 86.84(12) . . ? N1 Co1 N2 77.71(13) . . ? O5 Co2 O5 180.0(2) . 2_655 ? O5 Co2 O4 90.92(11) . 2_655 ? O5 Co2 O4 89.08(11) 2_655 2_655 ? O5 Co2 O4 89.08(11) . . ? O5 Co2 O4 90.92(11) 2_655 . ? O4 Co2 O4 180.00(10) 2_655 . ? O5 Co2 O2 91.38(11) . 2_655 ? O5 Co2 O2 88.62(11) 2_655 2_655 ? O4 Co2 O2 93.57(11) 2_655 2_655 ? O4 Co2 O2 86.43(11) . 2_655 ? O5 Co2 O2 88.62(11) . . ? O5 Co2 O2 91.38(11) 2_655 . ? O4 Co2 O2 86.43(11) 2_655 . ? O4 Co2 O2 93.57(11) . . ? O2 Co2 O2 180.0(2) 2_655 . ? C13 O1 Co1 124.9(3) . . ? C13 O2 Co2 134.2(3) . . ? C20 O3 Co1 120.8(3) . . ? C20 O4 Co2 140.9(3) . . ? C27 O5 Co2 141.9(3) . . ? C27 O5 Co1 101.8(3) . . ? Co2 O5 Co1 109.92(12) . . ? C1 N1 C12 117.7(4) . . ? C1 N1 Co1 127.5(3) . . ? C12 N1 Co1 114.6(3) . . ? C10 N2 C11 118.3(4) . . ? C10 N2 Co1 128.8(3) . . ? C11 N2 Co1 112.7(3) . . ? N3 N3 C18 113.7(4) 2_666 . ? N4 N4 C25 113.5(5) 2_546 . ? N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.6(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C12 116.9(4) . . ? C3 C4 C5 124.5(4) . . ? C12 C4 C5 118.6(4) . . ? C6 C5 C4 121.2(5) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 122.2(4) . . ? C5 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C11 C7 C8 117.1(4) . . ? C11 C7 C6 118.0(5) . . ? C8 C7 C6 124.8(4) . . ? C9 C8 C7 119.9(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 118.9(5) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? N2 C10 C9 123.1(5) . . ? N2 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? N2 C11 C7 122.6(4) . . ? N2 C11 C12 117.1(3) . . ? C7 C11 C12 120.2(4) . . ? N1 C12 C4 123.0(4) . . ? N1 C12 C11 117.3(4) . . ? C4 C12 C11 119.7(4) . . ? O2 C13 O1 125.8(4) . . ? O2 C13 C14 117.7(4) . . ? O1 C13 C14 116.5(4) . . ? C19 C14 C15 119.3(4) . . ? C19 C14 C13 120.7(4) . . ? C15 C14 C13 120.0(4) . . ? C14 C15 C16 120.3(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 119.8(5) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 119.7(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 120.1(4) . . ? C19 C18 N3 124.8(4) . . ? C17 C18 N3 115.1(4) . . ? C14 C19 C18 120.8(4) . . ? C14 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? O4 C20 O3 125.6(4) . . ? O4 C20 C21 116.6(4) . . ? O3 C20 C21 117.7(4) . . ? C22 C21 C26 118.0(4) . . ? C22 C21 C20 119.6(4) . . ? C26 C21 C20 122.3(4) . . ? C21 C22 C23 121.1(5) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 121.3(5) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 118.0(4) . . ? C23 C24 H24 121.0 . . ? C25 C24 H24 121.0 . . ? C24 C25 C26 120.6(4) . . ? C24 C25 N4 123.8(4) . . ? C26 C25 N4 115.6(4) . . ? C21 C26 C25 120.9(4) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? O6 C27 O5 119.3(4) . . ? O6 C27 C28 122.3(4) . . ? O5 C27 C28 118.4(4) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Co1 O1 C13 -106.5(3) . . . . ? O5 Co1 O1 C13 -7.9(3) . . . . ? N1 Co1 O1 C13 154.9(3) . . . . ? N2 Co1 O1 C13 78.1(3) . . . . ? O5 Co2 O2 C13 -57.7(4) . . . . ? O5 Co2 O2 C13 122.3(4) 2_655 . . . ? O4 Co2 O2 C13 -148.7(4) 2_655 . . . ? O4 Co2 O2 C13 31.3(4) . . . . ? O2 Co2 O2 C13 127(100) 2_655 . . . ? O1 Co1 O3 C20 59.4(3) . . . . ? O5 Co1 O3 C20 -46.5(3) . . . . ? N1 Co1 O3 C20 162.4(3) . . . . ? N2 Co1 O3 C20 -161.5(9) . . . . ? O5 Co2 O4 C20 -6.7(4) . . . . ? O5 Co2 O4 C20 173.3(4) 2_655 . . . ? O4 Co2 O4 C20 31(100) 2_655 . . . ? O2 Co2 O4 C20 84.8(4) 2_655 . . . ? O2 Co2 O4 C20 -95.2(4) . . . . ? O5 Co2 O5 C27 -9(100) 2_655 . . . ? O4 Co2 O5 C27 -78.0(5) 2_655 . . . ? O4 Co2 O5 C27 102.0(5) . . . . ? O2 Co2 O5 C27 15.6(5) 2_655 . . . ? O2 Co2 O5 C27 -164.4(5) . . . . ? O5 Co2 O5 Co1 -153(100) 2_655 . . . ? O4 Co2 O5 Co1 137.55(13) 2_655 . . . ? O4 Co2 O5 Co1 -42.45(13) . . . . ? O2 Co2 O5 Co1 -128.85(13) 2_655 . . . ? O2 Co2 O5 Co1 51.15(13) . . . . ? O3 Co1 O5 C27 -94.6(3) . . . . ? O1 Co1 O5 C27 165.3(2) . . . . ? N1 Co1 O5 C27 18.9(4) . . . . ? N2 Co1 O5 C27 79.0(3) . . . . ? O3 Co1 O5 Co2 63.94(14) . . . . ? O1 Co1 O5 Co2 -36.20(15) . . . . ? N1 Co1 O5 Co2 177.41(18) . . . . ? N2 Co1 O5 Co2 -122.46(15) . . . . ? O3 Co1 N1 C1 -6.6(3) . . . . ? O1 Co1 N1 C1 93.2(3) . . . . ? O5 Co1 N1 C1 -119.9(3) . . . . ? N2 Co1 N1 C1 177.7(3) . . . . ? O3 Co1 N1 C12 170.1(2) . . . . ? O1 Co1 N1 C12 -90.1(3) . . . . ? O5 Co1 N1 C12 56.7(4) . . . . ? N2 Co1 N1 C12 -5.7(2) . . . . ? O3 Co1 N2 C10 144.2(9) . . . . ? O1 Co1 N2 C10 -76.3(4) . . . . ? O5 Co1 N2 C10 28.6(4) . . . . ? N1 Co1 N2 C10 -179.0(4) . . . . ? O3 Co1 N2 C11 -30.8(11) . . . . ? O1 Co1 N2 C11 108.7(3) . . . . ? O5 Co1 N2 C11 -146.4(3) . . . . ? N1 Co1 N2 C11 5.9(3) . . . . ? C12 N1 C1 C2 -1.8(6) . . . . ? Co1 N1 C1 C2 174.8(3) . . . . ? N1 C1 C2 C3 0.8(7) . . . . ? C1 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C12 -0.5(6) . . . . ? C2 C3 C4 C5 179.9(4) . . . . ? C3 C4 C5 C6 179.8(5) . . . . ? C12 C4 C5 C6 0.2(7) . . . . ? C4 C5 C6 C7 1.2(8) . . . . ? C5 C6 C7 C11 -1.8(7) . . . . ? C5 C6 C7 C8 178.9(5) . . . . ? C11 C7 C8 C9 0.4(7) . . . . ? C6 C7 C8 C9 179.7(5) . . . . ? C7 C8 C9 C10 -0.1(7) . . . . ? C11 N2 C10 C9 1.0(6) . . . . ? Co1 N2 C10 C9 -173.7(3) . . . . ? C8 C9 C10 N2 -0.7(7) . . . . ? C10 N2 C11 C7 -0.7(6) . . . . ? Co1 N2 C11 C7 174.9(3) . . . . ? C10 N2 C11 C12 178.9(4) . . . . ? Co1 N2 C11 C12 -5.5(4) . . . . ? C8 C7 C11 N2 -0.1(6) . . . . ? C6 C7 C11 N2 -179.4(4) . . . . ? C8 C7 C11 C12 -179.6(4) . . . . ? C6 C7 C11 C12 1.0(6) . . . . ? C1 N1 C12 C4 1.7(5) . . . . ? Co1 N1 C12 C4 -175.3(3) . . . . ? C1 N1 C12 C11 -178.3(3) . . . . ? Co1 N1 C12 C11 4.7(4) . . . . ? C3 C4 C12 N1 -0.5(6) . . . . ? C5 C4 C12 N1 179.1(4) . . . . ? C3 C4 C12 C11 179.5(4) . . . . ? C5 C4 C12 C11 -0.9(6) . . . . ? N2 C11 C12 N1 0.7(5) . . . . ? C7 C11 C12 N1 -179.7(3) . . . . ? N2 C11 C12 C4 -179.3(3) . . . . ? C7 C11 C12 C4 0.3(6) . . . . ? Co2 O2 C13 O1 19.2(6) . . . . ? Co2 O2 C13 C14 -159.8(3) . . . . ? Co1 O1 C13 O2 21.3(6) . . . . ? Co1 O1 C13 C14 -159.7(2) . . . . ? O2 C13 C14 C19 164.4(4) . . . . ? O1 C13 C14 C19 -14.8(5) . . . . ? O2 C13 C14 C15 -15.7(6) . . . . ? O1 C13 C14 C15 165.2(4) . . . . ? C19 C14 C15 C16 -0.1(7) . . . . ? C13 C14 C15 C16 180.0(4) . . . . ? C14 C15 C16 C17 -1.1(8) . . . . ? C15 C16 C17 C18 0.4(8) . . . . ? C16 C17 C18 C19 1.4(7) . . . . ? C16 C17 C18 N3 -179.2(4) . . . . ? N3 N3 C18 C19 -2.4(7) 2_666 . . . ? N3 N3 C18 C17 178.3(5) 2_666 . . . ? C15 C14 C19 C18 1.9(6) . . . . ? C13 C14 C19 C18 -178.2(3) . . . . ? C17 C18 C19 C14 -2.6(6) . . . . ? N3 C18 C19 C14 178.1(4) . . . . ? Co2 O4 C20 O3 32.5(7) . . . . ? Co2 O4 C20 C21 -151.2(3) . . . . ? Co1 O3 C20 O4 3.2(5) . . . . ? Co1 O3 C20 C21 -173.1(2) . . . . ? O4 C20 C21 C22 8.2(6) . . . . ? O3 C20 C21 C22 -175.2(4) . . . . ? O4 C20 C21 C26 -167.6(4) . . . . ? O3 C20 C21 C26 9.0(6) . . . . ? C26 C21 C22 C23 -1.0(7) . . . . ? C20 C21 C22 C23 -177.0(5) . . . . ? C21 C22 C23 C24 1.5(9) . . . . ? C22 C23 C24 C25 -0.6(9) . . . . ? C23 C24 C25 C26 -0.7(8) . . . . ? C23 C24 C25 N4 179.2(5) . . . . ? N4 N4 C25 C24 -2.5(7) 2_546 . . . ? N4 N4 C25 C26 177.4(4) 2_546 . . . ? C22 C21 C26 C25 -0.3(6) . . . . ? C20 C21 C26 C25 175.6(3) . . . . ? C24 C25 C26 C21 1.1(6) . . . . ? N4 C25 C26 C21 -178.8(4) . . . . ? Co2 O5 C27 O6 -142.6(4) . . . . ? Co1 O5 C27 O6 3.5(5) . . . . ? Co2 O5 C27 C28 39.3(7) . . . . ? Co1 O5 C27 C28 -174.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.545 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.090 # Attachment 'Compound 8.CIF' data_tyz054m _database_code_depnum_ccdc_archive 'CCDC 651805' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Cd N4 O5' _chemical_formula_weight 578.84 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' O O 0.0106 0.0060 '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' Cd Cd -0.8075 1.2024 '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 16.6386(7) _cell_length_b 6.3953(3) _cell_length_c 27.2889(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.700(2) _cell_angle_gamma 90.00 _cell_volume 2678.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7259 _exptl_absorpt_correction_T_max 0.9193 _exptl_absorpt_process_details 'Sadabs; SHELDRICK 1996' _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 16229 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6539 _reflns_number_gt 5404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.0540P)^2^+2.3043P] 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 6539 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.236 _refine_ls_restrained_S_all 1.236 _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 0.482052(15) 0.68432(4) 0.331428(10) 0.02496(9) Uani 1 1 d . . . O1W O 0.4244(2) 0.3709(5) 0.28938(14) 0.0379(7) Uani 1 1 d . . . O1 O 0.35603(18) 0.7023(5) 0.34683(13) 0.0404(7) Uani 1 1 d . . . O2 O 0.39051(17) 1.0271(5) 0.33754(13) 0.0435(7) Uani 1 1 d . . . O3 O -0.44623(16) 1.3368(4) 0.25066(11) 0.0327(6) Uani 1 1 d . . . O4 O -0.39562(16) 1.5753(5) 0.31431(11) 0.0346(6) Uani 1 1 d . . . N1 N 0.5975(2) 0.8909(5) 0.38939(12) 0.0298(7) Uani 1 1 d . . . N2 N 0.5411(2) 0.5262(5) 0.41721(13) 0.0345(7) Uani 1 1 d . . . N3 N -0.0118(2) 1.1003(6) 0.31115(17) 0.0443(9) Uani 1 1 d . . . N4 N -0.0316(2) 1.2860(6) 0.31276(16) 0.0409(9) Uani 1 1 d . . . C1 C 0.6259(3) 1.0646(7) 0.37551(18) 0.0447(10) Uani 1 1 d . . . H1B H 0.5968 1.1143 0.3411 0.054 Uiso 1 1 calc R . . C2 C 0.6969(4) 1.1774(9) 0.4093(2) 0.0620(15) Uani 1 1 d . . . H2A H 0.7157 1.2972 0.3976 0.074 Uiso 1 1 calc R . . C3 C 0.7385(4) 1.1079(10) 0.4603(2) 0.0647(15) Uani 1 1 d . . . H3B H 0.7851 1.1835 0.4840 0.078 Uiso 1 1 calc R . . C4 C 0.7114(3) 0.9239(9) 0.47693(18) 0.0512(12) Uani 1 1 d . . . C5 C 0.7504(4) 0.8436(10) 0.5304(2) 0.077(2) Uani 1 1 d . . . H5A H 0.7966 0.9149 0.5556 0.092 Uiso 1 1 calc R . . C6 C 0.7204(5) 0.6667(10) 0.5443(2) 0.077(2) Uani 1 1 d . . . H6A H 0.7472 0.6169 0.5788 0.092 Uiso 1 1 calc R . . C7 C 0.6488(4) 0.5541(8) 0.50721(18) 0.0521(12) Uani 1 1 d . . . C8 C 0.6148(5) 0.3717(9) 0.5204(2) 0.0680(17) Uani 1 1 d . . . H8A H 0.6383 0.3196 0.5549 0.082 Uiso 1 1 calc R . . C9 C 0.5474(5) 0.2718(9) 0.4823(3) 0.0709(18) Uani 1 1 d . . . H9A H 0.5251 0.1493 0.4904 0.085 Uiso 1 1 calc R . . C10 C 0.5122(4) 0.3534(8) 0.4313(2) 0.0501(12) Uani 1 1 d . . . H10A H 0.4660 0.2830 0.4058 0.060 Uiso 1 1 calc R . . C11 C 0.6080(3) 0.6275(6) 0.45412(16) 0.0340(9) Uani 1 1 d . . . C12 C 0.6392(3) 0.8170(6) 0.43937(15) 0.0330(8) Uani 1 1 d . . . C13 C 0.3378(2) 0.8918(7) 0.34013(14) 0.0299(8) Uani 1 1 d . . . C14 C 0.2466(2) 0.9578(6) 0.33373(15) 0.0284(8) Uani 1 1 d . . . C15 C 0.1902(3) 0.8076(7) 0.33817(18) 0.0377(9) Uani 1 1 d . . . H15A H 0.2093 0.6706 0.3465 0.045 Uiso 1 1 calc R . . C16 C 0.1051(3) 0.8593(7) 0.3303(2) 0.0433(11) Uani 1 1 d . . . H16A H 0.0670 0.7570 0.3326 0.052 Uiso 1 1 calc R . . C17 C 0.0772(2) 1.0644(7) 0.31895(17) 0.0358(9) Uani 1 1 d . . . C18 C 0.1333(3) 1.2164(7) 0.31371(19) 0.0387(10) Uani 1 1 d . . . H18A H 0.1142 1.3532 0.3051 0.046 Uiso 1 1 calc R . . C19 C 0.2179(2) 1.1618(6) 0.32145(18) 0.0360(9) Uani 1 1 d . . . H19A H 0.2558 1.2630 0.3184 0.043 Uiso 1 1 calc R . . C20 C -0.1219(2) 1.3161(7) 0.30442(17) 0.0359(9) Uani 1 1 d . . . C21 C -0.1829(2) 1.1569(6) 0.28824(17) 0.0344(9) Uani 1 1 d . . . H21A H -0.1667 1.0230 0.2823 0.041 Uiso 1 1 calc R . . C22 C -0.2685(2) 1.1996(6) 0.28094(16) 0.0313(8) Uani 1 1 d . . . H22A H -0.3100 1.0938 0.2699 0.038 Uiso 1 1 calc R . . C23 C -0.2927(2) 1.3984(6) 0.28999(14) 0.0249(7) Uani 1 1 d . . . C24 C -0.2305(2) 1.5565(7) 0.30688(18) 0.0370(9) Uani 1 1 d . . . H24A H -0.2460 1.6892 0.3141 0.044 Uiso 1 1 calc R . . C25 C -0.1456(2) 1.5153(7) 0.31283(19) 0.0416(10) Uani 1 1 d . . . H25A H -0.1045 1.6221 0.3225 0.050 Uiso 1 1 calc R . . C26 C -0.3854(2) 1.4420(6) 0.28412(14) 0.0252(7) Uani 1 1 d . . . H2W1 H 0.451(3) 0.331(8) 0.281(2) 0.033(15) Uiso 1 1 d . . . H1W1 H 0.411(4) 0.222(10) 0.306(2) 0.08(2) Uiso 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 0.01756(13) 0.03059(15) 0.02848(14) 0.00096(11) 0.01083(10) 0.00265(10) O1W 0.0336(16) 0.0350(17) 0.054(2) -0.0074(14) 0.0265(15) 0.0006(13) O1 0.0306(14) 0.0418(18) 0.0538(18) 0.0070(14) 0.0217(13) 0.0174(13) O2 0.0241(13) 0.0497(19) 0.0594(19) 0.0048(15) 0.0189(13) 0.0012(13) O3 0.0212(12) 0.0420(16) 0.0379(15) -0.0100(12) 0.0145(11) -0.0050(11) O4 0.0217(12) 0.0392(16) 0.0445(16) -0.0112(13) 0.0146(11) 0.0035(11) N1 0.0265(15) 0.0319(17) 0.0306(16) -0.0002(13) 0.0106(13) 0.0014(13) N2 0.0391(18) 0.0348(18) 0.0329(17) 0.0009(14) 0.0175(15) -0.0010(14) N3 0.0174(15) 0.048(2) 0.069(3) -0.002(2) 0.0185(16) 0.0079(15) N4 0.0184(15) 0.047(2) 0.058(2) -0.0047(18) 0.0158(15) 0.0041(14) C1 0.047(2) 0.043(3) 0.041(2) 0.008(2) 0.014(2) -0.006(2) C2 0.063(3) 0.051(3) 0.069(4) -0.001(3) 0.022(3) -0.025(3) C3 0.057(3) 0.066(4) 0.055(3) -0.008(3) 0.005(3) -0.028(3) C4 0.049(3) 0.052(3) 0.040(2) -0.005(2) 0.002(2) -0.005(2) C5 0.081(4) 0.079(4) 0.037(3) -0.004(3) -0.014(3) -0.014(3) C6 0.103(5) 0.073(4) 0.030(3) 0.008(3) -0.001(3) 0.000(4) C7 0.074(3) 0.044(3) 0.033(2) 0.006(2) 0.014(2) 0.008(2) C8 0.109(5) 0.054(3) 0.043(3) 0.020(2) 0.031(3) 0.008(3) C9 0.112(5) 0.045(3) 0.067(4) 0.019(3) 0.048(4) -0.005(3) C10 0.063(3) 0.044(3) 0.051(3) 0.003(2) 0.030(2) -0.010(2) C11 0.043(2) 0.032(2) 0.031(2) 0.0017(16) 0.0180(18) 0.0056(17) C12 0.034(2) 0.033(2) 0.0293(19) -0.0045(16) 0.0095(16) 0.0045(17) C13 0.0177(16) 0.046(2) 0.0277(18) -0.0007(16) 0.0103(14) 0.0038(15) C14 0.0174(15) 0.036(2) 0.0329(19) -0.0011(16) 0.0107(14) 0.0050(14) C15 0.0244(18) 0.033(2) 0.059(3) 0.0043(19) 0.0192(18) 0.0090(16) C16 0.0238(19) 0.038(2) 0.073(3) 0.002(2) 0.024(2) 0.0013(16) C17 0.0166(16) 0.040(2) 0.049(2) -0.0049(19) 0.0116(16) 0.0062(15) C18 0.0266(19) 0.031(2) 0.060(3) 0.0010(19) 0.0182(19) 0.0086(16) C19 0.0222(18) 0.037(2) 0.051(2) 0.0017(18) 0.0161(17) 0.0026(15) C20 0.0179(16) 0.043(2) 0.047(2) -0.0015(19) 0.0127(16) 0.0064(16) C21 0.0185(16) 0.036(2) 0.047(2) -0.0038(18) 0.0101(16) 0.0089(15) C22 0.0178(16) 0.035(2) 0.041(2) -0.0050(17) 0.0110(15) -0.0004(15) C23 0.0135(14) 0.0312(18) 0.0306(18) -0.0015(15) 0.0092(13) 0.0025(13) C24 0.0233(18) 0.030(2) 0.061(3) -0.0063(19) 0.0189(18) 0.0014(15) C25 0.0183(17) 0.038(2) 0.069(3) -0.007(2) 0.0174(18) -0.0023(16) C26 0.0175(15) 0.0301(19) 0.0298(18) 0.0022(15) 0.0112(14) 0.0013(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 Cd1 O1 2.295(3) . ? Cd1 O3 2.301(3) 2_545 ? Cd1 O1W 2.325(3) . ? Cd1 O4 2.362(2) 1_645 ? Cd1 N1 2.365(3) . ? Cd1 N2 2.386(3) . ? O1W H2W1 0.62(5) . ? O1W H1W1 1.11(7) . ? O1 C13 1.246(5) . ? O2 C13 1.253(5) . ? O3 C26 1.264(4) . ? O3 Cd1 2.301(3) 2 ? O4 C26 1.242(4) . ? O4 Cd1 2.362(2) 1_465 ? N1 C1 1.319(5) . ? N1 C12 1.354(5) . ? N2 C10 1.320(5) . ? N2 C11 1.345(5) . ? N3 N4 1.238(5) . ? N3 C17 1.429(4) . ? N4 C20 1.442(4) . ? C1 C2 1.388(7) . ? C1 H1B 0.9300 . ? C2 C3 1.367(8) . ? C2 H2A 0.9300 . ? C3 C4 1.397(8) . ? C3 H3B 0.9300 . ? C4 C12 1.419(6) . ? C4 C5 1.443(7) . ? C5 C6 1.348(9) . ? C5 H5A 0.9300 . ? C6 C7 1.426(8) . ? C6 H6A 0.9300 . ? C7 C8 1.401(8) . ? C7 C11 1.422(6) . ? C8 C9 1.359(9) . ? C8 H8A 0.9300 . ? C9 C10 1.388(8) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.436(6) . ? C13 C14 1.519(5) . ? C14 C15 1.381(6) . ? C14 C19 1.385(5) . ? C15 C16 1.387(5) . ? C15 H15A 0.9300 . ? C16 C17 1.386(6) . ? C16 H16A 0.9300 . ? C17 C18 1.394(6) . ? C18 C19 1.385(5) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C25 1.379(6) . ? C20 C21 1.384(6) . ? C21 C22 1.388(5) . ? C21 H21A 0.9300 . ? C22 C23 1.384(5) . ? C22 H22A 0.9300 . ? C23 C24 1.391(5) . ? C23 C26 1.515(4) . ? C24 C25 1.384(5) . ? C24 H24A 0.9300 . ? C25 H25A 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 O1 Cd1 O3 104.21(10) . 2_545 ? O1 Cd1 O1W 84.34(11) . . ? O3 Cd1 O1W 88.98(11) 2_545 . ? O1 Cd1 O4 165.65(10) . 1_645 ? O3 Cd1 O4 81.48(10) 2_545 1_645 ? O1W Cd1 O4 82.58(11) . 1_645 ? O1 Cd1 N1 114.42(11) . . ? O3 Cd1 N1 104.64(11) 2_545 . ? O1W Cd1 N1 152.34(11) . . ? O4 Cd1 N1 75.97(10) 1_645 . ? O1 Cd1 N2 84.30(11) . . ? O3 Cd1 N2 171.41(10) 2_545 . ? O1W Cd1 N2 93.09(12) . . ? O4 Cd1 N2 90.52(11) 1_645 . ? N1 Cd1 N2 70.13(11) . . ? Cd1 O1W H2W1 108(5) . . ? Cd1 O1W H1W1 130(3) . . ? H2W1 O1W H1W1 94(5) . . ? C13 O1 Cd1 102.1(2) . . ? C26 O3 Cd1 139.8(2) . 2 ? C26 O4 Cd1 133.0(2) . 1_465 ? C1 N1 C12 118.8(4) . . ? C1 N1 Cd1 124.6(3) . . ? C12 N1 Cd1 116.5(3) . . ? C10 N2 C11 118.3(4) . . ? C10 N2 Cd1 125.6(3) . . ? C11 N2 Cd1 116.0(3) . . ? N4 N3 C17 115.1(4) . . ? N3 N4 C20 113.5(4) . . ? N1 C1 C2 123.7(4) . . ? N1 C1 H1B 118.2 . . ? C2 C1 H1B 118.2 . . ? C3 C2 C1 118.4(5) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 120.2(5) . . ? C2 C3 H3B 119.9 . . ? C4 C3 H3B 119.9 . . ? C3 C4 C12 117.5(4) . . ? C3 C4 C5 123.6(5) . . ? C12 C4 C5 118.9(5) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C7 121.6(5) . . ? C5 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C8 C7 C11 117.1(5) . . ? C8 C7 C6 123.2(5) . . ? C11 C7 C6 119.7(5) . . ? C9 C8 C7 119.4(5) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 C10 119.7(5) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 123.1(5) . . ? N2 C10 H10A 118.4 . . ? C9 C10 H10A 118.4 . . ? N2 C11 C7 122.4(4) . . ? N2 C11 C12 118.8(3) . . ? C7 C11 C12 118.9(4) . . ? N1 C12 C4 121.4(4) . . ? N1 C12 C11 118.5(4) . . ? C4 C12 C11 120.1(4) . . ? O1 C13 O2 123.0(3) . . ? O1 C13 C14 117.6(3) . . ? O2 C13 C14 119.4(4) . . ? C15 C14 C19 119.6(3) . . ? C15 C14 C13 118.7(3) . . ? C19 C14 C13 121.6(3) . . ? C14 C15 C16 120.5(4) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C17 C16 C15 119.6(4) . . ? C17 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? C16 C17 C18 120.2(3) . . ? C16 C17 N3 115.1(4) . . ? C18 C17 N3 124.7(4) . . ? C19 C18 C17 119.4(4) . . ? C19 C18 H18A 120.3 . . ? C17 C18 H18A 120.3 . . ? C14 C19 C18 120.6(4) . . ? C14 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C25 C20 C21 120.7(3) . . ? C25 C20 N4 116.4(4) . . ? C21 C20 N4 122.9(4) . . ? C20 C21 C22 119.1(4) . . ? C20 C21 H21A 120.4 . . ? C22 C21 H21A 120.4 . . ? C23 C22 C21 120.5(4) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C22 C23 C24 119.8(3) . . ? C22 C23 C26 120.3(3) . . ? C24 C23 C26 119.9(3) . . ? C25 C24 C23 119.7(4) . . ? C25 C24 H24A 120.2 . . ? C23 C24 H24A 120.2 . . ? C20 C25 C24 120.1(4) . . ? C20 C25 H25A 119.9 . . ? C24 C25 H25A 119.9 . . ? O4 C26 O3 124.6(3) . . ? O4 C26 C23 116.8(3) . . ? O3 C26 C23 118.5(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 O3 Cd1 O1 C13 -53.5(3) 2_545 . . . ? O1W Cd1 O1 C13 -141.0(3) . . . . ? O4 Cd1 O1 C13 -165.4(3) 1_645 . . . ? N1 Cd1 O1 C13 60.1(3) . . . . ? N2 Cd1 O1 C13 125.3(3) . . . . ? O1 Cd1 N1 C1 -107.9(3) . . . . ? O3 Cd1 N1 C1 5.5(4) 2_545 . . . ? O1W Cd1 N1 C1 122.8(4) . . . . ? O4 Cd1 N1 C1 82.6(3) 1_645 . . . ? N2 Cd1 N1 C1 178.4(4) . . . . ? O1 Cd1 N1 C12 75.6(3) . . . . ? O3 Cd1 N1 C12 -171.0(3) 2_545 . . . ? O1W Cd1 N1 C12 -53.7(4) . . . . ? O4 Cd1 N1 C12 -93.9(3) 1_645 . . . ? N2 Cd1 N1 C12 1.9(3) . . . . ? O1 Cd1 N2 C10 59.2(4) . . . . ? O3 Cd1 N2 C10 -128.6(7) 2_545 . . . ? O1W Cd1 N2 C10 -24.8(4) . . . . ? O4 Cd1 N2 C10 -107.4(4) 1_645 . . . ? N1 Cd1 N2 C10 177.7(4) . . . . ? O1 Cd1 N2 C11 -119.0(3) . . . . ? O3 Cd1 N2 C11 53.2(8) 2_545 . . . ? O1W Cd1 N2 C11 157.0(3) . . . . ? O4 Cd1 N2 C11 74.4(3) 1_645 . . . ? N1 Cd1 N2 C11 -0.4(3) . . . . ? C17 N3 N4 C20 179.6(4) . . . . ? C12 N1 C1 C2 0.2(7) . . . . ? Cd1 N1 C1 C2 -176.3(4) . . . . ? N1 C1 C2 C3 -1.7(9) . . . . ? C1 C2 C3 C4 2.1(10) . . . . ? C2 C3 C4 C12 -1.1(9) . . . . ? C2 C3 C4 C5 -178.2(6) . . . . ? C3 C4 C5 C6 179.0(7) . . . . ? C12 C4 C5 C6 1.9(10) . . . . ? C4 C5 C6 C7 -1.0(11) . . . . ? C5 C6 C7 C8 -178.8(7) . . . . ? C5 C6 C7 C11 0.7(10) . . . . ? C11 C7 C8 C9 1.8(9) . . . . ? C6 C7 C8 C9 -178.7(6) . . . . ? C7 C8 C9 C10 -1.1(10) . . . . ? C11 N2 C10 C9 0.1(7) . . . . ? Cd1 N2 C10 C9 -178.0(4) . . . . ? C8 C9 C10 N2 0.1(9) . . . . ? C10 N2 C11 C7 0.6(6) . . . . ? Cd1 N2 C11 C7 178.9(3) . . . . ? C10 N2 C11 C12 -179.2(4) . . . . ? Cd1 N2 C11 C12 -1.0(5) . . . . ? C8 C7 C11 N2 -1.5(7) . . . . ? C6 C7 C11 N2 178.9(5) . . . . ? C8 C7 C11 C12 178.3(5) . . . . ? C6 C7 C11 C12 -1.2(7) . . . . ? C1 N1 C12 C4 0.9(6) . . . . ? Cd1 N1 C12 C4 177.7(3) . . . . ? C1 N1 C12 C11 -179.8(4) . . . . ? Cd1 N1 C12 C11 -3.1(5) . . . . ? C3 C4 C12 N1 -0.5(7) . . . . ? C5 C4 C12 N1 176.8(5) . . . . ? C3 C4 C12 C11 -179.7(5) . . . . ? C5 C4 C12 C11 -2.5(7) . . . . ? N2 C11 C12 N1 2.8(6) . . . . ? C7 C11 C12 N1 -177.1(4) . . . . ? N2 C11 C12 C4 -178.0(4) . . . . ? C7 C11 C12 C4 2.1(6) . . . . ? Cd1 O1 C13 O2 -13.2(4) . . . . ? Cd1 O1 C13 C14 165.4(3) . . . . ? O1 C13 C14 C15 3.1(5) . . . . ? O2 C13 C14 C15 -178.2(4) . . . . ? O1 C13 C14 C19 -174.2(4) . . . . ? O2 C13 C14 C19 4.5(6) . . . . ? C19 C14 C15 C16 0.2(7) . . . . ? C13 C14 C15 C16 -177.2(4) . . . . ? C14 C15 C16 C17 -1.3(7) . . . . ? C15 C16 C17 C18 2.1(7) . . . . ? C15 C16 C17 N3 179.5(4) . . . . ? N4 N3 C17 C16 164.7(4) . . . . ? N4 N3 C17 C18 -18.0(7) . . . . ? C16 C17 C18 C19 -1.8(7) . . . . ? N3 C17 C18 C19 -179.0(4) . . . . ? C15 C14 C19 C18 0.2(6) . . . . ? C13 C14 C19 C18 177.4(4) . . . . ? C17 C18 C19 C14 0.7(7) . . . . ? N3 N4 C20 C25 171.5(4) . . . . ? N3 N4 C20 C21 -9.3(6) . . . . ? C25 C20 C21 C22 -0.5(7) . . . . ? N4 C20 C21 C22 -179.7(4) . . . . ? C20 C21 C22 C23 -0.4(6) . . . . ? C21 C22 C23 C24 -0.4(6) . . . . ? C21 C22 C23 C26 -177.5(4) . . . . ? C22 C23 C24 C25 2.1(6) . . . . ? C26 C23 C24 C25 179.2(4) . . . . ? C21 C20 C25 C24 2.2(7) . . . . ? N4 C20 C25 C24 -178.5(4) . . . . ? C23 C24 C25 C20 -3.0(7) . . . . ? Cd1 O4 C26 O3 5.3(6) 1_465 . . . ? Cd1 O4 C26 C23 -172.1(2) 1_465 . . . ? Cd1 O3 C26 O4 148.4(3) 2 . . . ? Cd1 O3 C26 C23 -34.3(6) 2 . . . ? C22 C23 C26 O4 146.8(4) . . . . ? C24 C23 C26 O4 -30.3(5) . . . . ? C22 C23 C26 O3 -30.7(5) . . . . ? C24 C23 C26 O3 152.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.734 _refine_diff_density_min -0.959 _refine_diff_density_rms 0.119 # Attachment 'Compound 9.cif' data_xb0926m _database_code_depnum_ccdc_archive 'CCDC 651806' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C66 H40 N10 O12 Y2' _chemical_formula_sum 'C66 H40 N10 O12 Y2' _chemical_formula_weight 1342.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Y Y -2.7962 3.5667 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 13.852(6) _cell_length_b 11.785(5) _cell_length_c 19.365(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.722(7) _cell_angle_gamma 90.00 _cell_volume 3011(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1036 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 17.62 _exptl_crystal_description block _exptl_crystal_colour orang-red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 1.990 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 14712 _diffrn_reflns_av_R_equivalents 0.1588 _diffrn_reflns_av_sigmaI/netI 0.2311 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.10 _reflns_number_total 5324 _reflns_number_gt 2168 _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^)+(0.0994P)^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 0.0045(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5324 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2052 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.2351 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 Y1 Y 0.82370(6) 0.43814(7) 1.01647(5) 0.0484(4) Uani 1 1 d . . . N1 N 0.8331(6) 0.2503(6) 0.9521(4) 0.057(2) Uani 1 1 d . . . N2 N 0.6534(6) 0.3561(6) 0.9443(4) 0.058(2) Uani 1 1 d . . . N3 N 0.5917(6) 0.7675(7) 0.7556(5) 0.068(3) Uani 1 1 d . . . N4 N 0.5471(6) 0.7069(8) 0.7884(5) 0.077(3) Uani 1 1 d . . . N5 N 0.5144(7) 0.9553(7) 0.9867(6) 0.082(3) Uani 1 1 d . . . O1 O 0.8663(5) 0.4962(5) 0.9168(3) 0.0559(17) Uani 1 1 d . . . O2 O 1.0102(5) 0.5898(5) 0.9235(4) 0.066(2) Uani 1 1 d . . . O3 O 0.2749(5) 0.5555(5) 0.8985(4) 0.0651(18) Uani 1 1 d . . . O4 O 0.1848(5) 0.7097(5) 0.8984(4) 0.069(2) Uani 1 1 d . . . O5 O 0.7136(5) 0.6011(5) 0.9818(3) 0.0547(17) Uani 1 1 d . . . O6 O 0.8690(5) 0.6282(5) 1.0577(4) 0.0649(19) Uani 1 1 d . . . C1 C 0.9201(7) 0.1999(9) 0.9553(6) 0.072(3) Uani 1 1 d . . . H1 H 0.9803 0.2387 0.9762 0.087 Uiso 1 1 calc R . . C2 C 0.9246(9) 0.0904(9) 0.9283(7) 0.086(4) Uani 1 1 d . . . H2 H 0.9869 0.0575 0.9317 0.103 Uiso 1 1 calc R . . C3 C 0.8361(10) 0.0317(10) 0.8968(7) 0.093(4) Uani 1 1 d . . . H3 H 0.8388 -0.0418 0.8799 0.111 Uiso 1 1 calc R . . C4 C 0.7418(9) 0.0824(9) 0.8900(6) 0.073(3) Uani 1 1 d . . . C5 C 0.6470(10) 0.0283(9) 0.8551(6) 0.083(4) Uani 1 1 d . . . H5 H 0.6462 -0.0439 0.8356 0.100 Uiso 1 1 calc R . . C6 C 0.5585(9) 0.0812(8) 0.8503(6) 0.075(3) Uani 1 1 d . . . H6 H 0.4978 0.0440 0.8279 0.089 Uiso 1 1 calc R . . C7 C 0.5558(7) 0.1947(8) 0.8791(5) 0.060(3) Uani 1 1 d . . . C8 C 0.4651(7) 0.2535(9) 0.8744(6) 0.067(3) Uani 1 1 d . . . H8 H 0.4024 0.2202 0.8525 0.080 Uiso 1 1 calc R . . C9 C 0.4718(7) 0.3604(9) 0.9027(6) 0.071(3) Uani 1 1 d . . . H9 H 0.4127 0.4011 0.8987 0.085 Uiso 1 1 calc R . . C10 C 0.5648(7) 0.4092(9) 0.9374(6) 0.068(3) Uani 1 1 d . . . H10 H 0.5662 0.4817 0.9568 0.082 Uiso 1 1 calc R . . C11 C 0.6482(7) 0.2490(8) 0.9153(5) 0.052(3) Uani 1 1 d . . . C12 C 0.7449(7) 0.1919(8) 0.9199(5) 0.054(3) Uani 1 1 d . . . C13 C 0.9147(7) 0.5737(8) 0.8970(5) 0.046(2) Uani 1 1 d . . . C14 C 0.8573(7) 0.6590(8) 0.8398(5) 0.053(3) Uani 1 1 d . . . C15 C 0.7509(6) 0.6640(8) 0.8213(5) 0.050(2) Uani 1 1 d . . . H15 H 0.7159 0.6147 0.8426 0.060 Uiso 1 1 calc R . . C16 C 0.6988(7) 0.7442(8) 0.7703(6) 0.057(3) Uani 1 1 d . . . C17 C 0.7508(7) 0.8193(8) 0.7384(5) 0.062(3) Uani 1 1 d . . . H17 H 0.7155 0.8729 0.7050 0.074 Uiso 1 1 calc R . . C18 C 0.8559(7) 0.8133(8) 0.7572(5) 0.062(3) Uani 1 1 d . . . H18 H 0.8908 0.8624 0.7356 0.075 Uiso 1 1 calc R . . C19 C 0.9102(7) 0.7333(8) 0.8086(5) 0.059(3) Uani 1 1 d . . . H19 H 0.9805 0.7302 0.8214 0.071 Uiso 1 1 calc R . . C20 C 0.4433(7) 0.7410(9) 0.7813(6) 0.062(3) Uani 1 1 d . . . C21 C 0.3923(7) 0.8305(9) 0.7370(5) 0.066(3) Uani 1 1 d . . . H21 H 0.4231 0.8688 0.7074 0.079 Uiso 1 1 calc R . . C22 C 0.2974(8) 0.8612(8) 0.7375(6) 0.069(3) Uani 1 1 d . . . H22 H 0.2640 0.9195 0.7073 0.083 Uiso 1 1 calc R . . C23 C 0.2490(7) 0.8064(8) 0.7828(5) 0.060(3) Uani 1 1 d . . . H23 H 0.1857 0.8307 0.7842 0.072 Uiso 1 1 calc R . . C24 C 0.2975(7) 0.7148(8) 0.8257(5) 0.054(3) Uani 1 1 d . . . C25 C 0.3933(7) 0.6823(9) 0.8240(5) 0.065(3) Uani 1 1 d . . . H25 H 0.4250 0.6205 0.8515 0.078 Uiso 1 1 calc R . . C26 C 0.2491(7) 0.6564(9) 0.8761(5) 0.053(3) Uani 1 1 d . . . C27 C 0.7802(8) 0.6660(8) 1.0247(5) 0.053(3) Uani 1 1 d . . . C28 C 0.7503(7) 0.7843(8) 1.0371(5) 0.057(3) Uani 1 1 d . . . C29 C 0.8180(8) 0.8566(9) 1.0830(6) 0.076(3) Uani 1 1 d . . . H29 H 0.8834 0.8315 1.1066 0.092 Uiso 1 1 calc R . . C30 C 0.7901(10) 0.9687(10) 1.0951(7) 0.098(4) Uani 1 1 d . . . H30 H 0.8377 1.0184 1.1238 0.118 Uiso 1 1 calc R . . C31 C 0.6915(9) 1.0029(9) 1.0639(7) 0.084(4) Uani 1 1 d . . . H31 H 0.6720 1.0758 1.0723 0.100 Uiso 1 1 calc R . . C32 C 0.6204(8) 0.9293(9) 1.0198(6) 0.065(3) Uani 1 1 d . . . C33 C 0.6524(8) 0.8227(8) 1.0040(5) 0.064(3) Uani 1 1 d . . . H33 H 0.6071 0.7765 0.9705 0.077 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 Y1 0.0380(5) 0.0393(5) 0.0669(7) 0.0008(5) 0.0143(4) 0.0033(5) N1 0.048(5) 0.050(5) 0.080(7) -0.009(4) 0.030(5) 0.001(4) N2 0.053(5) 0.037(5) 0.080(6) -0.001(4) 0.014(4) 0.003(4) N3 0.047(6) 0.072(7) 0.084(7) 0.012(5) 0.020(5) 0.004(5) N4 0.045(5) 0.097(8) 0.095(8) 0.030(6) 0.030(5) 0.014(5) N5 0.079(7) 0.063(7) 0.106(8) 0.006(5) 0.032(5) 0.024(5) O1 0.054(4) 0.043(4) 0.072(5) -0.001(3) 0.023(4) -0.002(3) O2 0.045(4) 0.060(5) 0.083(5) 0.013(3) 0.005(4) -0.003(3) O3 0.066(4) 0.043(4) 0.089(5) 0.003(4) 0.027(4) 0.006(4) O4 0.061(4) 0.063(5) 0.098(6) 0.017(4) 0.044(4) 0.021(4) O5 0.050(4) 0.046(4) 0.068(5) -0.002(3) 0.017(4) 0.007(3) O6 0.044(4) 0.053(4) 0.091(6) -0.010(4) 0.011(4) 0.007(3) C1 0.049(6) 0.052(7) 0.120(10) -0.014(6) 0.032(6) 0.002(5) C2 0.073(8) 0.053(8) 0.138(12) -0.003(7) 0.044(8) 0.010(6) C3 0.100(10) 0.057(8) 0.132(12) -0.016(7) 0.052(9) 0.006(7) C4 0.077(8) 0.053(8) 0.093(9) -0.015(6) 0.032(7) -0.014(6) C5 0.099(10) 0.050(7) 0.111(11) -0.018(6) 0.047(8) -0.014(7) C6 0.084(9) 0.041(7) 0.098(9) -0.008(6) 0.026(7) -0.028(6) C7 0.053(7) 0.061(7) 0.062(8) 0.002(5) 0.010(5) -0.011(6) C8 0.039(6) 0.068(8) 0.089(9) -0.001(6) 0.014(6) -0.019(5) C9 0.044(7) 0.064(8) 0.101(9) 0.010(6) 0.017(6) 0.006(6) C10 0.035(6) 0.063(7) 0.099(9) 0.001(6) 0.007(6) 0.010(5) C11 0.048(6) 0.063(7) 0.046(7) 0.001(5) 0.015(5) -0.004(5) C12 0.049(6) 0.045(6) 0.068(7) 0.007(5) 0.020(5) -0.001(5) C13 0.037(6) 0.051(6) 0.049(6) -0.009(5) 0.010(5) 0.011(5) C14 0.048(6) 0.057(7) 0.054(7) 0.004(5) 0.016(5) 0.007(5) C15 0.033(5) 0.057(6) 0.057(7) 0.004(5) 0.012(5) -0.002(5) C16 0.039(6) 0.061(7) 0.067(8) 0.000(5) 0.008(5) 0.007(5) C17 0.059(7) 0.063(7) 0.069(8) 0.009(5) 0.026(6) 0.014(6) C18 0.054(7) 0.058(7) 0.079(8) 0.004(6) 0.027(6) 0.007(5) C19 0.043(6) 0.054(7) 0.079(8) 0.007(6) 0.019(6) 0.005(5) C20 0.055(7) 0.059(7) 0.072(8) 0.012(6) 0.017(6) 0.009(5) C21 0.048(6) 0.072(8) 0.074(8) 0.014(6) 0.013(6) 0.006(6) C22 0.067(8) 0.056(7) 0.082(9) 0.019(6) 0.021(6) 0.008(6) C23 0.039(6) 0.072(8) 0.069(8) 0.007(6) 0.016(5) 0.006(5) C24 0.036(6) 0.068(7) 0.058(7) 0.000(5) 0.016(5) 0.003(5) C25 0.057(7) 0.065(7) 0.069(8) 0.011(6) 0.015(6) 0.005(6) C26 0.036(6) 0.063(7) 0.062(7) -0.007(6) 0.017(5) 0.000(5) C27 0.050(6) 0.046(6) 0.062(7) 0.006(5) 0.016(6) 0.001(5) C28 0.056(6) 0.036(6) 0.076(8) -0.003(5) 0.015(6) 0.000(5) C29 0.073(8) 0.051(7) 0.109(10) -0.012(6) 0.033(7) 0.001(6) C30 0.100(10) 0.068(9) 0.118(11) -0.037(7) 0.022(9) -0.007(7) C31 0.078(8) 0.046(7) 0.127(11) -0.004(7) 0.031(8) 0.019(7) C32 0.065(7) 0.048(7) 0.085(9) -0.001(6) 0.028(6) 0.010(6) C33 0.071(8) 0.047(7) 0.075(8) 0.000(5) 0.025(6) 0.006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Y1 O2 2.264(6) 3_767 ? Y1 O1 2.288(7) . ? Y1 O6 2.396(6) . ? Y1 O5 2.417(6) . ? Y1 O4 2.426(6) 3_667 ? Y1 O3 2.440(7) 3_667 ? Y1 N2 2.539(8) . ? Y1 N1 2.563(8) . ? Y1 C26 2.804(10) 3_667 ? N1 C1 1.329(11) . ? N1 C12 1.374(10) . ? N2 C10 1.348(11) . ? N2 C11 1.374(11) . ? N3 N4 1.239(10) . ? N3 C16 1.449(11) . ? N4 C20 1.458(11) . ? N5 N5 1.289(15) 3_677 ? N5 C32 1.446(13) . ? O1 C13 1.260(10) . ? O2 C13 1.278(10) . ? O2 Y1 2.264(6) 3_767 ? O3 C26 1.278(10) . ? O3 Y1 2.440(7) 3_667 ? O4 C26 1.269(10) . ? O4 Y1 2.426(6) 3_667 ? O5 C27 1.288(10) . ? O6 C27 1.281(10) . ? C1 C2 1.400(13) . ? C1 H1 0.9300 . ? C2 C3 1.378(15) . ? C2 H2 0.9300 . ? C3 C4 1.406(14) . ? C3 H3 0.9300 . ? C4 C12 1.410(13) . ? C4 C5 1.430(14) . ? C5 C6 1.353(14) . ? C5 H5 0.9300 . ? C6 C7 1.454(13) . ? C6 H6 0.9300 . ? C7 C11 1.412(12) . ? C7 C8 1.413(13) . ? C8 C9 1.366(13) . ? C8 H8 0.9300 . ? C9 C10 1.384(12) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.478(12) . ? C13 C14 1.528(12) . ? C14 C19 1.393(12) . ? C14 C15 1.408(11) . ? C15 C16 1.398(12) . ? C15 H15 0.9300 . ? C16 C17 1.398(12) . ? C17 C18 1.391(11) . ? C17 H17 0.9300 . ? C18 C19 1.410(12) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.406(12) . ? C20 C25 1.411(13) . ? C21 C22 1.365(12) . ? C21 H21 0.9300 . ? C22 C23 1.413(13) . ? C22 H22 0.9300 . ? C23 C24 1.403(12) . ? C23 H23 0.9300 . ? C24 C25 1.392(12) . ? C24 C26 1.508(13) . ? C25 H25 0.9300 . ? C26 Y1 2.804(10) 3_667 ? C27 C28 1.494(12) . ? C28 C29 1.374(12) . ? C28 C33 1.388(12) . ? C29 C30 1.416(14) . ? C29 H29 0.9300 . ? C30 C31 1.376(14) . ? C30 H30 0.9300 . ? C31 C32 1.391(14) . ? C31 H31 0.9300 . ? C32 C33 1.397(12) . ? C33 H33 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 O2 Y1 O1 89.7(2) 3_767 . ? O2 Y1 O6 80.9(2) 3_767 . ? O1 Y1 O6 83.8(2) . . ? O2 Y1 O5 135.6(2) 3_767 . ? O1 Y1 O5 80.3(2) . . ? O6 Y1 O5 55.2(2) . . ? O2 Y1 O4 78.4(2) 3_767 3_667 ? O1 Y1 O4 150.0(2) . 3_667 ? O6 Y1 O4 120.5(2) . 3_667 ? O5 Y1 O4 127.1(2) . 3_667 ? O2 Y1 O3 110.3(2) 3_767 3_667 ? O1 Y1 O3 154.3(2) . 3_667 ? O6 Y1 O3 83.7(2) . 3_667 ? O5 Y1 O3 74.2(2) . 3_667 ? O4 Y1 O3 53.9(2) 3_667 3_667 ? O2 Y1 N2 148.9(2) 3_767 . ? O1 Y1 N2 94.9(2) . . ? O6 Y1 N2 130.1(2) . . ? O5 Y1 N2 75.4(2) . . ? O4 Y1 N2 82.6(2) 3_667 . ? O3 Y1 N2 76.5(2) 3_667 . ? O2 Y1 N1 86.0(2) 3_767 . ? O1 Y1 N1 77.5(2) . . ? O6 Y1 N1 157.3(2) . . ? O5 Y1 N1 132.2(2) . . ? O4 Y1 N1 74.3(2) 3_667 . ? O3 Y1 N1 118.5(2) 3_667 . ? N2 Y1 N1 65.1(2) . . ? O2 Y1 C26 95.7(3) 3_767 3_667 ? O1 Y1 C26 171.1(2) . 3_667 ? O6 Y1 C26 103.9(3) . 3_667 ? O5 Y1 C26 100.5(3) . 3_667 ? O4 Y1 C26 26.9(2) 3_667 3_667 ? O3 Y1 C26 27.1(2) 3_667 3_667 ? N2 Y1 C26 76.9(3) . 3_667 ? N1 Y1 C26 95.8(3) . 3_667 ? C1 N1 C12 117.7(8) . . ? C1 N1 Y1 122.9(6) . . ? C12 N1 Y1 118.9(6) . . ? C10 N2 C11 117.0(8) . . ? C10 N2 Y1 122.9(6) . . ? C11 N2 Y1 119.9(6) . . ? N4 N3 C16 115.5(8) . . ? N3 N4 C20 115.1(9) . . ? N5 N5 C32 113.0(12) 3_677 . ? C13 O1 Y1 140.5(6) . . ? C13 O2 Y1 161.7(6) . 3_767 ? C26 O3 Y1 92.5(6) . 3_667 ? C26 O4 Y1 93.4(6) . 3_667 ? C27 O5 Y1 91.4(5) . . ? C27 O6 Y1 92.6(5) . . ? N1 C1 C2 122.6(10) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 119.5(10) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.3(10) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C12 116.0(10) . . ? C3 C4 C5 123.2(11) . . ? C12 C4 C5 120.8(10) . . ? C6 C5 C4 120.6(10) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 121.7(10) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C11 C7 C8 117.6(9) . . ? C11 C7 C6 118.9(9) . . ? C8 C7 C6 123.5(10) . . ? C9 C8 C7 118.4(9) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C8 C9 C10 121.2(10) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? N2 C10 C9 122.7(10) . . ? N2 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? N2 C11 C7 123.1(9) . . ? N2 C11 C12 117.4(8) . . ? C7 C11 C12 119.5(9) . . ? N1 C12 C4 123.9(9) . . ? N1 C12 C11 117.6(8) . . ? C4 C12 C11 118.5(9) . . ? O1 C13 O2 124.6(8) . . ? O1 C13 C14 119.3(8) . . ? O2 C13 C14 116.1(9) . . ? C19 C14 C15 120.8(9) . . ? C19 C14 C13 120.1(8) . . ? C15 C14 C13 119.1(8) . . ? C16 C15 C14 118.9(9) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 121.0(9) . . ? C15 C16 N3 123.0(9) . . ? C17 C16 N3 115.3(9) . . ? C18 C17 C16 119.4(9) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.6(10) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 119.3(9) . . ? C14 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C21 C20 C25 118.6(9) . . ? C21 C20 N4 124.2(9) . . ? C25 C20 N4 117.1(9) . . ? C22 C21 C20 120.1(10) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 121.6(10) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C24 C23 C22 119.2(9) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C25 C24 C23 119.1(9) . . ? C25 C24 C26 120.3(9) . . ? C23 C24 C26 120.5(8) . . ? C24 C25 C20 121.4(9) . . ? C24 C25 H25 119.3 . . ? C20 C25 H25 119.3 . . ? O4 C26 O3 119.9(9) . . ? O4 C26 C24 119.4(9) . . ? O3 C26 C24 120.7(8) . . ? O4 C26 Y1 59.7(5) . 3_667 ? O3 C26 Y1 60.4(5) . 3_667 ? C24 C26 Y1 173.0(6) . 3_667 ? O6 C27 O5 120.4(8) . . ? O6 C27 C28 121.0(9) . . ? O5 C27 C28 118.6(8) . . ? C29 C28 C33 118.3(9) . . ? C29 C28 C27 121.0(9) . . ? C33 C28 C27 120.7(9) . . ? C28 C29 C30 121.3(10) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 119.0(11) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C30 C31 C32 120.6(10) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C31 C32 C33 118.9(10) . . ? C31 C32 N5 125.0(9) . . ? C33 C32 N5 116.1(9) . . ? C28 C33 C32 121.5(10) . . ? C28 C33 H33 119.2 . . ? C32 C33 H33 119.2 . . ? 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 O2 Y1 N1 C1 -12.7(8) 3_767 . . . ? O1 Y1 N1 C1 77.9(8) . . . . ? O6 Y1 N1 C1 42.2(11) . . . . ? O5 Y1 N1 C1 142.1(7) . . . . ? O4 Y1 N1 C1 -91.7(8) 3_667 . . . ? O3 Y1 N1 C1 -123.7(8) 3_667 . . . ? N2 Y1 N1 C1 179.3(9) . . . . ? C26 Y1 N1 C1 -108.1(8) 3_667 . . . ? O2 Y1 N1 C12 159.4(7) 3_767 . . . ? O1 Y1 N1 C12 -110.1(7) . . . . ? O6 Y1 N1 C12 -145.7(7) . . . . ? O5 Y1 N1 C12 -45.9(8) . . . . ? O4 Y1 N1 C12 80.4(7) 3_667 . . . ? O3 Y1 N1 C12 48.4(7) 3_667 . . . ? N2 Y1 N1 C12 -8.6(6) . . . . ? C26 Y1 N1 C12 64.0(7) 3_667 . . . ? O2 Y1 N2 C10 159.3(7) 3_767 . . . ? O1 Y1 N2 C10 -103.2(8) . . . . ? O6 Y1 N2 C10 -17.2(9) . . . . ? O5 Y1 N2 C10 -24.7(7) . . . . ? O4 Y1 N2 C10 106.8(8) 3_667 . . . ? O3 Y1 N2 C10 52.2(8) 3_667 . . . ? N1 Y1 N2 C10 -177.1(8) . . . . ? C26 Y1 N2 C10 80.1(8) 3_667 . . . ? O2 Y1 N2 C11 -15.4(10) 3_767 . . . ? O1 Y1 N2 C11 82.1(7) . . . . ? O6 Y1 N2 C11 168.2(6) . . . . ? O5 Y1 N2 C11 160.7(7) . . . . ? O4 Y1 N2 C11 -67.8(7) 3_667 . . . ? O3 Y1 N2 C11 -122.4(7) 3_667 . . . ? N1 Y1 N2 C11 8.3(6) . . . . ? C26 Y1 N2 C11 -94.5(7) 3_667 . . . ? C16 N3 N4 C20 171.7(8) . . . . ? O2 Y1 O1 C13 -63.2(9) 3_767 . . . ? O6 Y1 O1 C13 17.7(9) . . . . ? O5 Y1 O1 C13 73.3(9) . . . . ? O4 Y1 O1 C13 -128.8(9) 3_667 . . . ? O3 Y1 O1 C13 79.0(10) 3_667 . . . ? N2 Y1 O1 C13 147.6(9) . . . . ? N1 Y1 O1 C13 -149.2(9) . . . . ? O2 Y1 O5 C27 -13.7(7) 3_767 . . . ? O1 Y1 O5 C27 -93.1(5) . . . . ? O6 Y1 O5 C27 -3.8(5) . . . . ? O4 Y1 O5 C27 100.6(6) 3_667 . . . ? O3 Y1 O5 C27 89.5(5) 3_667 . . . ? N2 Y1 O5 C27 169.2(6) . . . . ? N1 Y1 O5 C27 -156.2(5) . . . . ? C26 Y1 O5 C27 95.9(6) 3_667 . . . ? O2 Y1 O6 C27 176.9(6) 3_767 . . . ? O1 Y1 O6 C27 86.3(6) . . . . ? O5 Y1 O6 C27 3.9(5) . . . . ? O4 Y1 O6 C27 -112.4(6) 3_667 . . . ? O3 Y1 O6 C27 -71.3(6) 3_667 . . . ? N2 Y1 O6 C27 -4.9(7) . . . . ? N1 Y1 O6 C27 121.2(7) . . . . ? C26 Y1 O6 C27 -89.4(6) 3_667 . . . ? C12 N1 C1 C2 -1.0(16) . . . . ? Y1 N1 C1 C2 171.2(8) . . . . ? N1 C1 C2 C3 0.3(18) . . . . ? C1 C2 C3 C4 1.6(19) . . . . ? C2 C3 C4 C12 -2.7(18) . . . . ? C2 C3 C4 C5 177.2(11) . . . . ? C3 C4 C5 C6 179.9(12) . . . . ? C12 C4 C5 C6 -0.2(18) . . . . ? C4 C5 C6 C7 0.9(18) . . . . ? C5 C6 C7 C11 -2.2(16) . . . . ? C5 C6 C7 C8 179.2(11) . . . . ? C11 C7 C8 C9 2.1(15) . . . . ? C6 C7 C8 C9 -179.3(10) . . . . ? C7 C8 C9 C10 -2.0(16) . . . . ? C11 N2 C10 C9 -0.2(15) . . . . ? Y1 N2 C10 C9 -175.0(8) . . . . ? C8 C9 C10 N2 1.1(17) . . . . ? C10 N2 C11 C7 0.3(14) . . . . ? Y1 N2 C11 C7 175.3(7) . . . . ? C10 N2 C11 C12 177.5(8) . . . . ? Y1 N2 C11 C12 -7.5(11) . . . . ? C8 C7 C11 N2 -1.3(15) . . . . ? C6 C7 C11 N2 -180.0(9) . . . . ? C8 C7 C11 C12 -178.4(8) . . . . ? C6 C7 C11 C12 2.9(14) . . . . ? C1 N1 C12 C4 -0.2(15) . . . . ? Y1 N1 C12 C4 -172.7(8) . . . . ? C1 N1 C12 C11 -179.0(9) . . . . ? Y1 N1 C12 C11 8.5(11) . . . . ? C3 C4 C12 N1 2.0(16) . . . . ? C5 C4 C12 N1 -177.8(10) . . . . ? C3 C4 C12 C11 -179.3(10) . . . . ? C5 C4 C12 C11 0.9(15) . . . . ? N2 C11 C12 N1 -0.8(13) . . . . ? C7 C11 C12 N1 176.5(8) . . . . ? N2 C11 C12 C4 -179.6(9) . . . . ? C7 C11 C12 C4 -2.2(14) . . . . ? Y1 O1 C13 O2 63.9(13) . . . . ? Y1 O1 C13 C14 -113.4(9) . . . . ? Y1 O2 C13 O1 16(3) 3_767 . . . ? Y1 O2 C13 C14 -167.0(16) 3_767 . . . ? O1 C13 C14 C19 -169.4(9) . . . . ? O2 C13 C14 C19 13.0(13) . . . . ? O1 C13 C14 C15 12.9(13) . . . . ? O2 C13 C14 C15 -164.7(8) . . . . ? C19 C14 C15 C16 0.6(14) . . . . ? C13 C14 C15 C16 178.3(8) . . . . ? C14 C15 C16 C17 -0.6(15) . . . . ? C14 C15 C16 N3 -170.6(8) . . . . ? N4 N3 C16 C15 -3.8(15) . . . . ? N4 N3 C16 C17 -174.3(10) . . . . ? C15 C16 C17 C18 0.7(15) . . . . ? N3 C16 C17 C18 171.4(8) . . . . ? C16 C17 C18 C19 -0.8(15) . . . . ? C15 C14 C19 C18 -0.7(15) . . . . ? C13 C14 C19 C18 -178.4(8) . . . . ? C17 C18 C19 C14 0.9(15) . . . . ? N3 N4 C20 C21 4.3(16) . . . . ? N3 N4 C20 C25 -173.3(10) . . . . ? C25 C20 C21 C22 1.9(16) . . . . ? N4 C20 C21 C22 -175.6(10) . . . . ? C20 C21 C22 C23 1.2(16) . . . . ? C21 C22 C23 C24 -3.1(16) . . . . ? C22 C23 C24 C25 1.7(15) . . . . ? C22 C23 C24 C26 178.4(9) . . . . ? C23 C24 C25 C20 1.5(15) . . . . ? C26 C24 C25 C20 -175.3(9) . . . . ? C21 C20 C25 C24 -3.3(16) . . . . ? N4 C20 C25 C24 174.4(9) . . . . ? Y1 O4 C26 O3 5.5(9) 3_667 . . . ? Y1 O4 C26 C24 -172.0(7) 3_667 . . . ? Y1 O3 C26 O4 -5.5(9) 3_667 . . . ? Y1 O3 C26 C24 172.0(8) 3_667 . . . ? C25 C24 C26 O4 153.1(9) . . . . ? C23 C24 C26 O4 -23.6(14) . . . . ? C25 C24 C26 O3 -24.4(14) . . . . ? C23 C24 C26 O3 158.9(9) . . . . ? Y1 O6 C27 O5 -6.9(9) . . . . ? Y1 O6 C27 C28 170.9(8) . . . . ? Y1 O5 C27 O6 6.9(9) . . . . ? Y1 O5 C27 C28 -171.0(8) . . . . ? O6 C27 C28 C29 1.4(15) . . . . ? O5 C27 C28 C29 179.2(10) . . . . ? O6 C27 C28 C33 -176.8(9) . . . . ? O5 C27 C28 C33 1.1(14) . . . . ? C33 C28 C29 C30 -1.6(16) . . . . ? C27 C28 C29 C30 -179.8(10) . . . . ? C28 C29 C30 C31 4.2(19) . . . . ? C29 C30 C31 C32 -1.2(19) . . . . ? C30 C31 C32 C33 -4.1(18) . . . . ? C30 C31 C32 N5 177.6(11) . . . . ? N5 N5 C32 C31 -13.6(18) 3_677 . . . ? N5 N5 C32 C33 168.1(12) 3_677 . . . ? C29 C28 C33 C32 -4.0(15) . . . . ? C27 C28 C33 C32 174.2(9) . . . . ? C31 C32 C33 C28 6.9(16) . . . . ? N5 C32 C33 C28 -174.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.291 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.105 # Attachment 'Compound 10.cif' data_xb1128 _database_code_depnum_ccdc_archive 'CCDC 651807' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C66 H40 N10 O12 Sm2' _chemical_formula_sum 'C66 H40 N10 O12 Sm2' _chemical_formula_weight 1465.78 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' Sm Sm -0.1638 3.4418 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 13.771(6) _cell_length_b 11.733(5) _cell_length_c 18.983(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.627(5) _cell_angle_gamma 90.00 _cell_volume 2923(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1913 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 21.45 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 2.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 10752 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.1388 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.10 _reflns_number_total 5016 _reflns_number_gt 2637 _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^)+(0.0409P)^2^+8.3376P] 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 5016 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1415 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.0994 _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 Sm1 Sm 0.82275(4) 0.43905(4) 1.01748(3) 0.03524(19) Uani 1 1 d . . . N1 N 0.8287(7) 0.2473(7) 0.9504(5) 0.050(3) Uani 1 1 d . . . N2 N 0.6523(6) 0.3549(7) 0.9418(5) 0.039(2) Uani 1 1 d . . . N3 N 0.5949(7) 0.7719(8) 0.7543(5) 0.050(3) Uani 1 1 d . . . N4 N 0.5494(7) 0.7100(8) 0.7873(5) 0.057(3) Uani 1 1 d . . . N5 N 0.5132(8) 0.9571(7) 0.9882(6) 0.065(3) Uani 1 1 d . . . O1 O 0.8665(5) 0.4984(5) 0.9135(4) 0.0371(18) Uani 1 1 d . . . O2 O 1.0087(5) 0.5881(6) 0.9201(4) 0.050(2) Uani 1 1 d . . . O3 O 0.2810(5) 0.5584(6) 0.8965(4) 0.0470(18) Uani 1 1 d . . . O4 O 0.1869(6) 0.7098(6) 0.8939(4) 0.056(2) Uani 1 1 d . . . O5 O 0.7100(5) 0.6039(6) 0.9824(4) 0.046(2) Uani 1 1 d . . . O6 O 0.8672(6) 0.6357(5) 1.0549(4) 0.048(2) Uani 1 1 d . . . C1 C 0.9152(9) 0.1986(9) 0.9536(7) 0.059(3) Uani 1 1 d . . . H1 H 0.9759 0.2380 0.9740 0.071 Uiso 1 1 calc R . . C2 C 0.9179(10) 0.0880(11) 0.9269(8) 0.075(4) Uani 1 1 d . . . H2 H 0.9802 0.0535 0.9311 0.090 Uiso 1 1 calc R . . C3 C 0.8316(11) 0.0318(10) 0.8953(8) 0.075(4) Uani 1 1 d . . . H3 H 0.8339 -0.0420 0.8779 0.090 Uiso 1 1 calc R . . C4 C 0.7379(9) 0.0834(9) 0.8883(7) 0.054(3) Uani 1 1 d . . . C5 C 0.6418(11) 0.0308(10) 0.8528(7) 0.065(4) Uani 1 1 d . . . H5 H 0.6400 -0.0415 0.8324 0.078 Uiso 1 1 calc R . . C6 C 0.5551(11) 0.0838(10) 0.8488(7) 0.067(4) Uani 1 1 d . . . H6 H 0.4937 0.0472 0.8261 0.081 Uiso 1 1 calc R . . C7 C 0.5535(9) 0.1957(9) 0.8783(6) 0.047(3) Uani 1 1 d . . . C8 C 0.4626(9) 0.2550(10) 0.8724(6) 0.055(3) Uani 1 1 d . . . H8 H 0.3994 0.2217 0.8501 0.066 Uiso 1 1 calc R . . C9 C 0.4700(9) 0.3625(11) 0.9006(7) 0.061(4) Uani 1 1 d . . . H9 H 0.4120 0.4059 0.8965 0.073 Uiso 1 1 calc R . . C10 C 0.5654(9) 0.4051(9) 0.9350(7) 0.055(4) Uani 1 1 d . . . H10 H 0.5685 0.4774 0.9556 0.066 Uiso 1 1 calc R . . C11 C 0.6464(8) 0.2476(8) 0.9134(6) 0.040(3) Uani 1 1 d . . . C12 C 0.7395(8) 0.1921(9) 0.9189(6) 0.042(3) Uani 1 1 d . . . C13 C 0.9144(8) 0.5752(9) 0.8937(6) 0.036(3) Uani 1 1 d . . . C14 C 0.8581(7) 0.6615(8) 0.8383(5) 0.032(2) Uani 1 1 d . . . C15 C 0.7541(8) 0.6672(9) 0.8199(6) 0.040(3) Uani 1 1 d . . . H15 H 0.7194 0.6151 0.8403 0.048 Uiso 1 1 calc R . . C16 C 0.6998(8) 0.7496(9) 0.7712(6) 0.038(3) Uani 1 1 d . . . C17 C 0.7537(9) 0.8221(10) 0.7385(6) 0.050(3) Uani 1 1 d . . . H17 H 0.7191 0.8755 0.7037 0.060 Uiso 1 1 calc R . . C18 C 0.8573(9) 0.8145(9) 0.7575(6) 0.053(3) Uani 1 1 d . . . H18 H 0.8923 0.8641 0.7356 0.063 Uiso 1 1 calc R . . C19 C 0.9110(8) 0.7371(9) 0.8072(6) 0.047(3) Uani 1 1 d . . . H19 H 0.9818 0.7348 0.8201 0.057 Uiso 1 1 calc R . . C20 C 0.4472(9) 0.7424(9) 0.7795(7) 0.046(3) Uani 1 1 d . . . C21 C 0.3967(9) 0.8302(10) 0.7348(7) 0.058(3) Uani 1 1 d . . . H21 H 0.4273 0.8673 0.7038 0.070 Uiso 1 1 calc R . . C22 C 0.3010(9) 0.8633(10) 0.7360(7) 0.058(4) Uani 1 1 d . . . H22 H 0.2678 0.9240 0.7072 0.069 Uiso 1 1 calc R . . C23 C 0.2555(8) 0.8052(9) 0.7804(6) 0.047(3) Uani 1 1 d . . . H23 H 0.1910 0.8278 0.7810 0.057 Uiso 1 1 calc R . . C24 C 0.3006(8) 0.7168(9) 0.8232(6) 0.041(3) Uani 1 1 d . . . C25 C 0.3990(9) 0.6848(9) 0.8213(6) 0.053(3) Uani 1 1 d . . . H25 H 0.4313 0.6229 0.8494 0.063 Uiso 1 1 calc R . . C26 C 0.2536(8) 0.6569(9) 0.8738(6) 0.042(3) Uani 1 1 d . . . C27 C 0.7753(9) 0.6667(9) 1.0216(6) 0.041(3) Uani 1 1 d . . . C28 C 0.7489(9) 0.7878(9) 1.0354(6) 0.051(3) Uani 1 1 d . . . C29 C 0.8186(9) 0.8600(9) 1.0813(7) 0.061(4) Uani 1 1 d . . . H29 H 0.8852 0.8363 1.1038 0.073 Uiso 1 1 calc R . . C30 C 0.7876(11) 0.9695(10) 1.0936(8) 0.077(4) Uani 1 1 d . . . H30 H 0.8348 1.0193 1.1235 0.092 Uiso 1 1 calc R . . C31 C 0.6898(11) 1.0048(10) 1.0627(8) 0.070(4) Uani 1 1 d . . . H31 H 0.6706 1.0782 1.0715 0.084 Uiso 1 1 calc R . . C32 C 0.6197(9) 0.9313(10) 1.0184(6) 0.051(3) Uani 1 1 d . . . C33 C 0.6502(8) 0.8232(8) 1.0040(6) 0.047(3) Uani 1 1 d . . . H33 H 0.6033 0.7743 0.9727 0.056 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 Sm1 0.0312(3) 0.0250(3) 0.0470(3) 0.0006(3) 0.0080(2) 0.0028(3) N1 0.046(6) 0.039(5) 0.063(7) -0.006(5) 0.012(5) 0.012(5) N2 0.023(5) 0.037(5) 0.056(6) 0.006(4) 0.010(4) 0.011(4) N3 0.041(6) 0.054(7) 0.053(7) 0.002(5) 0.012(5) 0.003(5) N4 0.042(6) 0.072(7) 0.062(7) 0.026(6) 0.022(6) 0.005(5) N5 0.072(7) 0.041(7) 0.088(8) 0.008(6) 0.034(6) 0.027(6) O1 0.022(4) 0.035(4) 0.053(5) 0.000(3) 0.009(4) 0.001(3) O2 0.027(4) 0.060(5) 0.058(5) 0.016(4) 0.006(4) -0.001(3) O3 0.055(5) 0.035(4) 0.051(5) 0.002(4) 0.016(4) 0.006(4) O4 0.060(5) 0.043(5) 0.078(6) 0.017(4) 0.042(5) 0.015(4) O5 0.043(5) 0.030(4) 0.061(5) -0.003(4) 0.012(4) 0.005(3) O6 0.052(5) 0.026(4) 0.063(5) 0.001(4) 0.016(4) 0.008(3) C1 0.050(8) 0.043(7) 0.082(10) -0.010(7) 0.015(7) -0.003(6) C2 0.057(9) 0.063(10) 0.111(12) -0.008(8) 0.034(9) 0.019(7) C3 0.082(11) 0.048(9) 0.109(12) -0.024(8) 0.052(10) 0.004(7) C4 0.065(9) 0.038(8) 0.061(8) -0.009(6) 0.021(7) -0.002(6) C5 0.080(10) 0.036(8) 0.080(10) -0.015(6) 0.025(9) -0.010(7) C6 0.078(10) 0.055(9) 0.065(9) -0.008(7) 0.017(8) -0.040(7) C7 0.061(8) 0.033(6) 0.043(7) 0.000(5) 0.011(6) -0.014(6) C8 0.039(8) 0.064(9) 0.048(8) 0.006(6) -0.008(6) -0.009(6) C9 0.046(8) 0.063(9) 0.066(9) -0.003(7) 0.006(7) 0.000(6) C10 0.050(8) 0.043(8) 0.063(9) -0.001(6) 0.005(7) 0.010(6) C11 0.048(7) 0.027(6) 0.047(8) 0.003(5) 0.017(6) -0.006(5) C12 0.044(7) 0.039(7) 0.044(7) 0.000(5) 0.014(6) -0.003(5) C13 0.035(7) 0.035(7) 0.038(7) -0.010(5) 0.013(5) 0.003(5) C14 0.030(6) 0.031(6) 0.036(7) 0.005(5) 0.010(5) 0.007(5) C15 0.036(7) 0.044(7) 0.044(7) -0.001(5) 0.018(6) 0.004(5) C16 0.041(7) 0.039(6) 0.037(7) 0.005(5) 0.014(6) 0.011(5) C17 0.047(8) 0.060(8) 0.045(8) 0.013(6) 0.015(6) 0.016(6) C18 0.072(9) 0.037(7) 0.057(8) 0.010(6) 0.031(7) 0.006(6) C19 0.032(7) 0.057(8) 0.051(8) -0.002(6) 0.010(6) 0.003(6) C20 0.041(7) 0.044(7) 0.053(8) 0.002(6) 0.015(6) 0.001(6) C21 0.050(8) 0.061(8) 0.062(9) 0.014(7) 0.014(7) 0.007(7) C22 0.051(8) 0.049(8) 0.058(9) 0.024(6) -0.006(7) 0.007(6) C23 0.040(7) 0.052(8) 0.044(7) -0.003(6) 0.004(6) -0.001(6) C24 0.037(7) 0.047(7) 0.039(7) 0.003(5) 0.011(6) 0.004(5) C25 0.059(8) 0.045(7) 0.047(8) 0.012(6) 0.006(7) 0.001(6) C26 0.032(7) 0.044(7) 0.048(8) -0.013(6) 0.008(6) 0.000(5) C27 0.041(7) 0.030(6) 0.052(8) 0.000(5) 0.014(6) 0.007(6) C28 0.052(8) 0.039(7) 0.059(8) 0.000(6) 0.013(7) 0.004(6) C29 0.057(8) 0.041(7) 0.082(10) -0.005(7) 0.016(8) 0.004(6) C30 0.081(11) 0.045(8) 0.092(11) -0.031(7) 0.006(9) -0.002(7) C31 0.089(11) 0.039(7) 0.086(11) -0.005(7) 0.032(9) 0.018(8) C32 0.068(8) 0.036(6) 0.060(8) 0.003(6) 0.036(7) 0.018(7) C33 0.059(8) 0.022(6) 0.056(8) -0.006(5) 0.015(6) 0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O2 2.286(7) 3_767 ? Sm1 O1 2.338(7) . ? Sm1 O6 2.437(6) . ? Sm1 O5 2.443(6) . ? Sm1 O4 2.456(7) 3_667 ? Sm1 O3 2.473(7) 3_667 ? Sm1 N2 2.551(8) . ? Sm1 N1 2.598(8) . ? Sm1 C26 2.819(12) 3_667 ? N1 C1 1.307(12) . ? N1 C12 1.358(12) . ? N2 C10 1.303(12) . ? N2 C11 1.363(12) . ? N3 N4 1.245(11) . ? N3 C16 1.405(12) . ? N4 C20 1.422(13) . ? N5 N5 1.201(16) 3_677 ? N5 C32 1.436(14) . ? O1 C13 1.241(12) . ? O2 C13 1.251(11) . ? O2 Sm1 2.286(7) 3_767 ? O3 C26 1.252(12) . ? O3 Sm1 2.473(7) 3_667 ? O4 C26 1.260(12) . ? O4 Sm1 2.456(7) 3_667 ? O5 C27 1.225(11) . ? O6 C27 1.284(11) . ? C1 C2 1.397(15) . ? C1 H1 0.9300 . ? C2 C3 1.332(16) . ? C2 H2 0.9300 . ? C3 C4 1.395(16) . ? C3 H3 0.9300 . ? C4 C12 1.399(14) . ? C4 C5 1.430(15) . ? C5 C6 1.328(16) . ? C5 H5 0.9300 . ? C6 C7 1.430(15) . ? C6 H6 0.9300 . ? C7 C11 1.391(13) . ? C7 C8 1.406(15) . ? C8 C9 1.362(15) . ? C8 H8 0.9300 . ? C9 C10 1.373(14) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.413(13) . ? C13 C14 1.496(13) . ? C14 C15 1.369(13) . ? C14 C19 1.389(14) . ? C15 C16 1.389(13) . ? C15 H15 0.9300 . ? C16 C17 1.393(14) . ? C17 C18 1.366(14) . ? C17 H17 0.9300 . ? C18 C19 1.356(14) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C25 1.359(15) . ? C20 C21 1.381(14) . ? C21 C22 1.380(15) . ? C21 H21 0.9300 . ? C22 C23 1.374(15) . ? C22 H22 0.9300 . ? C23 C24 1.348(13) . ? C23 H23 0.9300 . ? C24 C25 1.416(15) . ? C24 C26 1.487(14) . ? C25 H25 0.9300 . ? C26 Sm1 2.819(12) 3_667 ? C27 C28 1.508(14) . ? C28 C33 1.373(13) . ? C28 C29 1.375(14) . ? C29 C30 1.395(15) . ? C29 H29 0.9300 . ? C30 C31 1.360(16) . ? C30 H30 0.9300 . ? C31 C32 1.376(16) . ? C31 H31 0.9300 . ? C32 C33 1.389(13) . ? C33 H33 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 O2 Sm1 O1 89.9(2) 3_767 . ? O2 Sm1 O6 81.7(2) 3_767 . ? O1 Sm1 O6 81.8(2) . . ? O2 Sm1 O5 135.5(2) 3_767 . ? O1 Sm1 O5 80.7(2) . . ? O6 Sm1 O5 54.0(2) . . ? O2 Sm1 O4 78.6(2) 3_767 3_667 ? O1 Sm1 O4 150.6(2) . 3_667 ? O6 Sm1 O4 122.3(3) . 3_667 ? O5 Sm1 O4 126.0(2) . 3_667 ? O2 Sm1 O3 111.0(2) 3_767 3_667 ? O1 Sm1 O3 154.4(2) . 3_667 ? O6 Sm1 O3 86.6(2) . 3_667 ? O5 Sm1 O3 74.0(2) . 3_667 ? O4 Sm1 O3 52.8(2) 3_667 3_667 ? O2 Sm1 N2 148.7(3) 3_767 . ? O1 Sm1 N2 93.9(3) . . ? O6 Sm1 N2 129.6(2) . . ? O5 Sm1 N2 75.6(2) . . ? O4 Sm1 N2 83.1(3) 3_667 . ? O3 Sm1 N2 76.1(3) 3_667 . ? O2 Sm1 N1 87.5(3) 3_767 . ? O1 Sm1 N1 77.9(3) . . ? O6 Sm1 N1 156.9(3) . . ? O5 Sm1 N1 131.6(3) . . ? O4 Sm1 N1 74.7(3) 3_667 . ? O3 Sm1 N1 116.4(3) 3_667 . ? N2 Sm1 N1 63.2(3) . . ? O2 Sm1 C26 96.3(3) 3_767 3_667 ? O1 Sm1 C26 170.3(3) . 3_667 ? O6 Sm1 C26 106.3(3) . 3_667 ? O5 Sm1 C26 99.7(3) . 3_667 ? O4 Sm1 C26 26.5(2) 3_667 3_667 ? O3 Sm1 C26 26.3(2) 3_667 3_667 ? N2 Sm1 C26 76.9(3) . 3_667 ? N1 Sm1 C26 95.0(3) . 3_667 ? C1 N1 C12 120.2(9) . . ? C1 N1 Sm1 121.3(7) . . ? C12 N1 Sm1 118.1(7) . . ? C10 N2 C11 115.8(9) . . ? C10 N2 Sm1 122.8(7) . . ? C11 N2 Sm1 121.0(6) . . ? N4 N3 C16 114.5(9) . . ? N3 N4 C20 115.2(9) . . ? N5 N5 C32 114.6(14) 3_677 . ? C13 O1 Sm1 140.3(7) . . ? C13 O2 Sm1 163.4(7) . 3_767 ? C26 O3 Sm1 92.4(6) . 3_667 ? C26 O4 Sm1 93.0(7) . 3_667 ? C27 O5 Sm1 91.2(6) . . ? C27 O6 Sm1 90.1(6) . . ? N1 C1 C2 120.9(11) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C3 C2 C1 120.4(12) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.1(11) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C12 117.3(11) . . ? C3 C4 C5 123.7(11) . . ? C12 C4 C5 119.0(11) . . ? C6 C5 C4 120.8(11) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 121.9(11) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C11 C7 C8 119.3(10) . . ? C11 C7 C6 117.9(11) . . ? C8 C7 C6 122.8(11) . . ? C9 C8 C7 117.9(11) . . ? C9 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C8 C9 C10 118.1(12) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? N2 C10 C9 126.9(11) . . ? N2 C10 H10 116.6 . . ? C9 C10 H10 116.6 . . ? N2 C11 C7 122.0(10) . . ? N2 C11 C12 116.9(9) . . ? C7 C11 C12 121.0(10) . . ? N1 C12 C4 121.1(10) . . ? N1 C12 C11 119.5(9) . . ? C4 C12 C11 119.3(10) . . ? O1 C13 O2 123.3(10) . . ? O1 C13 C14 119.6(9) . . ? O2 C13 C14 117.0(10) . . ? C15 C14 C19 120.2(9) . . ? C15 C14 C13 119.5(10) . . ? C19 C14 C13 120.3(9) . . ? C14 C15 C16 121.0(10) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C17 118.0(10) . . ? C15 C16 N3 126.3(10) . . ? C17 C16 N3 115.7(10) . . ? C18 C17 C16 119.9(11) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 122.3(11) . . ? C19 C18 H18 118.9 . . ? C17 C18 H18 118.9 . . ? C18 C19 C14 118.5(10) . . ? C18 C19 H19 120.7 . . ? C14 C19 H19 120.7 . . ? C25 C20 C21 119.1(11) . . ? C25 C20 N4 116.7(11) . . ? C21 C20 N4 124.2(11) . . ? C22 C21 C20 120.3(12) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 119.1(11) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 122.6(11) . . ? C24 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? C23 C24 C25 117.3(11) . . ? C23 C24 C26 122.7(10) . . ? C25 C24 C26 119.9(10) . . ? C20 C25 C24 121.5(11) . . ? C20 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? O3 C26 O4 121.4(11) . . ? O3 C26 C24 121.0(10) . . ? O4 C26 C24 117.6(10) . . ? O3 C26 Sm1 61.2(6) . 3_667 ? O4 C26 Sm1 60.5(6) . 3_667 ? C24 C26 Sm1 173.3(7) . 3_667 ? O5 C27 O6 124.1(9) . . ? O5 C27 C28 120.1(10) . . ? O6 C27 C28 115.8(10) . . ? C33 C28 C29 119.9(10) . . ? C33 C28 C27 117.9(10) . . ? C29 C28 C27 122.1(10) . . ? C28 C29 C30 118.9(11) . . ? C28 C29 H29 120.6 . . ? C30 C29 H29 120.6 . . ? C31 C30 C29 121.5(12) . . ? C31 C30 H30 119.3 . . ? C29 C30 H30 119.3 . . ? C30 C31 C32 119.5(11) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C31 C32 C33 119.7(11) . . ? C31 C32 N5 123.7(10) . . ? C33 C32 N5 116.5(11) . . ? C28 C33 C32 120.6(11) . . ? C28 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? 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 O2 Sm1 N1 C1 -13.3(9) 3_767 . . . ? O1 Sm1 N1 C1 77.1(9) . . . . ? O6 Sm1 N1 C1 48.3(13) . . . . ? O5 Sm1 N1 C1 142.9(9) . . . . ? O4 Sm1 N1 C1 -92.2(9) 3_667 . . . ? O3 Sm1 N1 C1 -125.5(9) 3_667 . . . ? N2 Sm1 N1 C1 177.9(10) . . . . ? C26 Sm1 N1 C1 -109.4(9) 3_667 . . . ? O2 Sm1 N1 C12 159.3(8) 3_767 . . . ? O1 Sm1 N1 C12 -110.2(8) . . . . ? O6 Sm1 N1 C12 -139.1(8) . . . . ? O5 Sm1 N1 C12 -44.5(9) . . . . ? O4 Sm1 N1 C12 80.4(8) 3_667 . . . ? O3 Sm1 N1 C12 47.1(8) 3_667 . . . ? N2 Sm1 N1 C12 -9.5(7) . . . . ? C26 Sm1 N1 C12 63.2(8) 3_667 . . . ? O2 Sm1 N2 C10 159.3(8) 3_767 . . . ? O1 Sm1 N2 C10 -104.3(9) . . . . ? O6 Sm1 N2 C10 -21.7(10) . . . . ? O5 Sm1 N2 C10 -25.0(9) . . . . ? O4 Sm1 N2 C10 105.0(9) 3_667 . . . ? O3 Sm1 N2 C10 51.8(9) 3_667 . . . ? N1 Sm1 N2 C10 -178.6(10) . . . . ? C26 Sm1 N2 C10 78.8(9) 3_667 . . . ? O2 Sm1 N2 C11 -12.6(11) 3_767 . . . ? O1 Sm1 N2 C11 83.7(8) . . . . ? O6 Sm1 N2 C11 166.3(7) . . . . ? O5 Sm1 N2 C11 163.1(8) . . . . ? O4 Sm1 N2 C11 -66.9(8) 3_667 . . . ? O3 Sm1 N2 C11 -120.2(8) 3_667 . . . ? N1 Sm1 N2 C11 9.4(7) . . . . ? C26 Sm1 N2 C11 -93.1(8) 3_667 . . . ? C16 N3 N4 C20 170.9(9) . . . . ? O2 Sm1 O1 C13 -62.9(10) 3_767 . . . ? O6 Sm1 O1 C13 18.6(10) . . . . ? O5 Sm1 O1 C13 73.4(10) . . . . ? O4 Sm1 O1 C13 -129.1(10) 3_667 . . . ? O3 Sm1 O1 C13 82.6(11) 3_667 . . . ? N2 Sm1 O1 C13 148.1(10) . . . . ? N1 Sm1 O1 C13 -150.4(10) . . . . ? O2 Sm1 O5 C27 -10.2(8) 3_767 . . . ? O1 Sm1 O5 C27 -90.5(7) . . . . ? O6 Sm1 O5 C27 -3.9(6) . . . . ? O4 Sm1 O5 C27 102.9(7) 3_667 . . . ? O3 Sm1 O5 C27 93.6(7) 3_667 . . . ? N2 Sm1 O5 C27 173.0(7) . . . . ? N1 Sm1 O5 C27 -155.1(6) . . . . ? C26 Sm1 O5 C27 99.3(7) 3_667 . . . ? O2 Sm1 O6 C27 179.3(7) 3_767 . . . ? O1 Sm1 O6 C27 88.2(6) . . . . ? O5 Sm1 O6 C27 3.7(6) . . . . ? O4 Sm1 O6 C27 -109.9(6) 3_667 . . . ? O3 Sm1 O6 C27 -68.9(6) 3_667 . . . ? N2 Sm1 O6 C27 -0.2(8) . . . . ? N1 Sm1 O6 C27 116.6(8) . . . . ? C26 Sm1 O6 C27 -86.5(7) 3_667 . . . ? C12 N1 C1 C2 -2.0(19) . . . . ? Sm1 N1 C1 C2 170.5(9) . . . . ? N1 C1 C2 C3 2(2) . . . . ? C1 C2 C3 C4 0(2) . . . . ? C2 C3 C4 C12 -3(2) . . . . ? C2 C3 C4 C5 177.7(13) . . . . ? C3 C4 C5 C6 179.1(14) . . . . ? C12 C4 C5 C6 0.1(19) . . . . ? C4 C5 C6 C7 1(2) . . . . ? C5 C6 C7 C11 -1.5(19) . . . . ? C5 C6 C7 C8 177.8(12) . . . . ? C11 C7 C8 C9 1.3(17) . . . . ? C6 C7 C8 C9 -178.0(11) . . . . ? C7 C8 C9 C10 -2.1(18) . . . . ? C11 N2 C10 C9 -2.1(18) . . . . ? Sm1 N2 C10 C9 -174.4(9) . . . . ? C8 C9 C10 N2 3(2) . . . . ? C10 N2 C11 C7 1.1(15) . . . . ? Sm1 N2 C11 C7 173.6(8) . . . . ? C10 N2 C11 C12 178.8(10) . . . . ? Sm1 N2 C11 C12 -8.7(13) . . . . ? C8 C7 C11 N2 -0.7(16) . . . . ? C6 C7 C11 N2 178.6(10) . . . . ? C8 C7 C11 C12 -178.4(10) . . . . ? C6 C7 C11 C12 0.9(16) . . . . ? C1 N1 C12 C4 -0.9(17) . . . . ? Sm1 N1 C12 C4 -173.7(8) . . . . ? C1 N1 C12 C11 -177.7(11) . . . . ? Sm1 N1 C12 C11 9.6(13) . . . . ? C3 C4 C12 N1 3.5(18) . . . . ? C5 C4 C12 N1 -177.4(10) . . . . ? C3 C4 C12 C11 -179.7(11) . . . . ? C5 C4 C12 C11 -0.6(17) . . . . ? N2 C11 C12 N1 -0.9(15) . . . . ? C7 C11 C12 N1 176.9(10) . . . . ? N2 C11 C12 C4 -177.7(10) . . . . ? C7 C11 C12 C4 0.1(17) . . . . ? Sm1 O1 C13 O2 65.3(15) . . . . ? Sm1 O1 C13 C14 -111.6(10) . . . . ? Sm1 O2 C13 O1 11(3) 3_767 . . . ? Sm1 O2 C13 C14 -172.0(19) 3_767 . . . ? O1 C13 C14 C15 11.5(14) . . . . ? O2 C13 C14 C15 -165.6(9) . . . . ? O1 C13 C14 C19 -170.2(10) . . . . ? O2 C13 C14 C19 12.7(14) . . . . ? C19 C14 C15 C16 -1.3(16) . . . . ? C13 C14 C15 C16 177.0(9) . . . . ? C14 C15 C16 C17 3.6(16) . . . . ? C14 C15 C16 N3 -172.7(10) . . . . ? N4 N3 C16 C15 0.0(16) . . . . ? N4 N3 C16 C17 -176.3(10) . . . . ? C15 C16 C17 C18 -3.3(17) . . . . ? N3 C16 C17 C18 173.3(10) . . . . ? C16 C17 C18 C19 0.8(18) . . . . ? C17 C18 C19 C14 1.6(17) . . . . ? C15 C14 C19 C18 -1.4(16) . . . . ? C13 C14 C19 C18 -179.6(9) . . . . ? N3 N4 C20 C25 -172.8(10) . . . . ? N3 N4 C20 C21 4.7(17) . . . . ? C25 C20 C21 C22 3.7(18) . . . . ? N4 C20 C21 C22 -173.6(11) . . . . ? C20 C21 C22 C23 -2.1(18) . . . . ? C21 C22 C23 C24 0.0(18) . . . . ? C22 C23 C24 C25 0.3(16) . . . . ? C22 C23 C24 C26 177.3(10) . . . . ? C21 C20 C25 C24 -3.5(17) . . . . ? N4 C20 C25 C24 174.1(10) . . . . ? C23 C24 C25 C20 1.5(17) . . . . ? C26 C24 C25 C20 -175.6(10) . . . . ? Sm1 O3 C26 O4 -5.8(10) 3_667 . . . ? Sm1 O3 C26 C24 172.7(8) 3_667 . . . ? Sm1 O4 C26 O3 5.9(10) 3_667 . . . ? Sm1 O4 C26 C24 -172.8(8) 3_667 . . . ? C23 C24 C26 O3 159.7(10) . . . . ? C25 C24 C26 O3 -23.4(15) . . . . ? C23 C24 C26 O4 -21.7(15) . . . . ? C25 C24 C26 O4 155.3(10) . . . . ? Sm1 O5 C27 O6 7.3(12) . . . . ? Sm1 O5 C27 C28 -170.7(9) . . . . ? Sm1 O6 C27 O5 -7.3(12) . . . . ? Sm1 O6 C27 C28 170.8(9) . . . . ? O5 C27 C28 C33 1.4(17) . . . . ? O6 C27 C28 C33 -176.8(10) . . . . ? O5 C27 C28 C29 177.5(11) . . . . ? O6 C27 C28 C29 -0.7(17) . . . . ? C33 C28 C29 C30 -1.5(19) . . . . ? C27 C28 C29 C30 -177.5(12) . . . . ? C28 C29 C30 C31 2(2) . . . . ? C29 C30 C31 C32 0(2) . . . . ? C30 C31 C32 C33 -2.0(19) . . . . ? C30 C31 C32 N5 174.8(13) . . . . ? N5 N5 C32 C31 -9(2) 3_677 . . . ? N5 N5 C32 C33 168.1(14) 3_677 . . . ? C29 C28 C33 C32 -0.3(18) . . . . ? C27 C28 C33 C32 175.8(10) . . . . ? C31 C32 C33 C28 2.1(17) . . . . ? N5 C32 C33 C28 -174.9(11) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.060 _refine_diff_density_min -1.203 _refine_diff_density_rms 0.148 # Attachment 'Compound 11.cif' data_xb1121 _database_code_depnum_ccdc_archive 'CCDC 651808' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C66 H40 Er2 N10 O12' _chemical_formula_sum 'C66 H40 Er2 N10 O12' _chemical_formula_weight 1499.60 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' Er Er -0.2586 4.9576 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 13.728(4) _cell_length_b 11.688(4) _cell_length_c 19.196(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.743(4) _cell_angle_gamma 90.00 _cell_volume 2933.6(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1177 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 17.80 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1476 _exptl_absorpt_coefficient_mu 2.916 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 13946 _diffrn_reflns_av_R_equivalents 0.1541 _diffrn_reflns_av_sigmaI/netI 0.2220 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.10 _reflns_number_total 5210 _reflns_number_gt 2387 _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^)+(0.0849P)^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 0.0018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5210 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1906 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.2010 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 Er1 Er 0.82370(6) 0.43772(6) 1.01613(5) 0.0395(3) Uani 1 1 d . . . N1 N 0.8330(10) 0.2508(11) 0.9531(8) 0.048(4) Uani 1 1 d . . . N2 N 0.6537(10) 0.3559(11) 0.9435(8) 0.047(4) Uani 1 1 d . . . N3 N 0.5900(10) 0.7678(11) 0.7559(8) 0.051(4) Uani 1 1 d . . . N4 N 0.5486(10) 0.7077(13) 0.7905(9) 0.060(5) Uani 1 1 d . . . N5 N 0.5143(12) 0.9567(12) 0.9877(10) 0.071(5) Uani 1 1 d . . . O1 O 0.8670(8) 0.4961(9) 0.9172(7) 0.047(3) Uani 1 1 d . . . O2 O 1.0109(8) 0.5917(9) 0.9235(7) 0.058(4) Uani 1 1 d . . . O3 O 0.2750(8) 0.5563(9) 0.8987(7) 0.052(3) Uani 1 1 d . . . O4 O 0.1840(8) 0.7105(10) 0.8991(7) 0.054(4) Uani 1 1 d . . . O5 O 0.7157(8) 0.6014(9) 0.9814(7) 0.047(3) Uani 1 1 d . . . O6 O 0.8688(8) 0.6261(9) 1.0594(7) 0.054(3) Uani 1 1 d . . . C1 C 0.9208(14) 0.2010(17) 0.9552(12) 0.072(7) Uani 1 1 d . . . H1 H 0.9817 0.2404 0.9758 0.086 Uiso 1 1 calc R . . C2 C 0.9243(16) 0.0895(15) 0.9269(11) 0.065(6) Uani 1 1 d . . . H2 H 0.9869 0.0564 0.9295 0.078 Uiso 1 1 calc R . . C3 C 0.8348(17) 0.0303(16) 0.8957(13) 0.076(7) Uani 1 1 d . . . H3 H 0.8361 -0.0443 0.8792 0.091 Uiso 1 1 calc R . . C4 C 0.7432(15) 0.0847(14) 0.8897(12) 0.065(6) Uani 1 1 d . . . C5 C 0.6442(17) 0.0308(14) 0.8550(12) 0.067(6) Uani 1 1 d . . . H5 H 0.6433 -0.0434 0.8373 0.080 Uiso 1 1 calc R . . C6 C 0.5588(16) 0.0806(16) 0.8478(11) 0.065(6) Uani 1 1 d . . . H6 H 0.4984 0.0441 0.8220 0.079 Uiso 1 1 calc R . . C7 C 0.5541(14) 0.1932(16) 0.8791(11) 0.058(5) Uani 1 1 d . . . C8 C 0.4648(13) 0.2567(17) 0.8740(12) 0.064(6) Uani 1 1 d . . . H8 H 0.4016 0.2255 0.8489 0.077 Uiso 1 1 calc R . . C9 C 0.4682(13) 0.3652(15) 0.9056(10) 0.054(5) Uani 1 1 d . . . H9 H 0.4096 0.4045 0.9062 0.064 Uiso 1 1 calc R . . C10 C 0.5664(12) 0.4098(19) 0.9361(11) 0.070(7) Uani 1 1 d . . . H10 H 0.5708 0.4849 0.9528 0.084 Uiso 1 1 calc R . . C11 C 0.6496(12) 0.2488(13) 0.9150(10) 0.042(5) Uani 1 1 d . . . C12 C 0.7461(12) 0.1944(13) 0.9206(10) 0.042(4) Uani 1 1 d . . . C13 C 0.9143(12) 0.5768(13) 0.8959(9) 0.035(4) Uani 1 1 d . . . C14 C 0.8599(11) 0.6587(14) 0.8399(10) 0.041(4) Uani 1 1 d . . . C15 C 0.7502(12) 0.6620(14) 0.8210(10) 0.046(5) Uani 1 1 d . . . H15 H 0.7151 0.6095 0.8409 0.056 Uiso 1 1 calc R . . C16 C 0.6981(12) 0.7450(14) 0.7726(9) 0.040(4) Uani 1 1 d . . . C17 C 0.7528(14) 0.8188(16) 0.7372(10) 0.056(5) Uani 1 1 d . . . H17 H 0.7178 0.8694 0.7007 0.067 Uiso 1 1 calc R . . C18 C 0.8567(12) 0.8127(14) 0.7582(10) 0.048(5) Uani 1 1 d . . . H18 H 0.8927 0.8640 0.7383 0.057 Uiso 1 1 calc R . . C19 C 0.9111(12) 0.7315(13) 0.8091(10) 0.043(5) Uani 1 1 d . . . H19 H 0.9820 0.7279 0.8215 0.051 Uiso 1 1 calc R . . C20 C 0.4416(14) 0.7389(16) 0.7808(12) 0.063(6) Uani 1 1 d . . . C21 C 0.3903(13) 0.8303(15) 0.7359(11) 0.061(6) Uani 1 1 d . . . H21 H 0.4203 0.8686 0.7052 0.074 Uiso 1 1 calc R . . C22 C 0.2949(14) 0.8610(15) 0.7392(11) 0.057(5) Uani 1 1 d . . . H22 H 0.2613 0.9220 0.7108 0.068 Uiso 1 1 calc R . . C23 C 0.2481(12) 0.8055(14) 0.7822(10) 0.046(5) Uani 1 1 d . . . H23 H 0.1839 0.8291 0.7833 0.055 Uiso 1 1 calc R . . C24 C 0.2952(11) 0.7152(14) 0.8238(9) 0.039(4) Uani 1 1 d . . . C25 C 0.3966(12) 0.6837(15) 0.8235(10) 0.052(5) Uani 1 1 d . . . H25 H 0.4309 0.6244 0.8534 0.062 Uiso 1 1 calc R . . C26 C 0.2488(13) 0.6567(14) 0.8761(11) 0.049(5) Uani 1 1 d . . . C27 C 0.7778(14) 0.6649(14) 1.0264(12) 0.058(6) Uani 1 1 d . . . C28 C 0.7533(13) 0.7856(14) 1.0366(11) 0.046(5) Uani 1 1 d . . . C29 C 0.8217(16) 0.8557(14) 1.0849(11) 0.063(6) Uani 1 1 d . . . H29 H 0.8866 0.8290 1.1104 0.076 Uiso 1 1 calc R . . C30 C 0.7936(17) 0.9650(16) 1.0953(12) 0.073(7) Uani 1 1 d . . . H30 H 0.8427 1.0162 1.1220 0.088 Uiso 1 1 calc R . . C31 C 0.6928(19) 1.0009(16) 1.0665(13) 0.083(8) Uani 1 1 d . . . H31 H 0.6737 1.0717 1.0803 0.099 Uiso 1 1 calc R . . C32 C 0.6202(15) 0.9336(16) 1.0179(11) 0.056(5) Uani 1 1 d . . . C33 C 0.6528(13) 0.8230(15) 1.0025(10) 0.053(5) Uani 1 1 d . . . H33 H 0.6070 0.7752 0.9696 0.064 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 Er1 0.0279(4) 0.0364(4) 0.0550(6) 0.0003(5) 0.0141(3) 0.0028(4) N1 0.041(9) 0.042(8) 0.055(12) -0.012(8) 0.008(8) 0.002(7) N2 0.039(9) 0.034(8) 0.063(12) 0.002(7) 0.007(7) 0.003(6) N3 0.025(8) 0.056(10) 0.069(13) 0.011(9) 0.012(8) 0.010(7) N4 0.024(8) 0.081(12) 0.074(14) 0.006(10) 0.011(8) -0.003(8) N5 0.060(10) 0.045(10) 0.113(16) -0.001(10) 0.034(10) 0.024(8) O1 0.041(7) 0.034(6) 0.065(10) 0.006(6) 0.014(6) 0.005(5) O2 0.037(7) 0.047(8) 0.083(11) 0.012(7) 0.009(7) -0.008(6) O3 0.057(7) 0.036(7) 0.070(10) 0.010(7) 0.029(6) -0.002(6) O4 0.052(8) 0.063(8) 0.057(10) 0.013(7) 0.031(7) 0.028(6) O5 0.036(6) 0.045(7) 0.061(10) 0.002(6) 0.016(6) 0.014(5) O6 0.041(7) 0.032(6) 0.085(11) 0.013(6) 0.011(7) 0.025(5) C1 0.041(11) 0.080(15) 0.11(2) -0.001(14) 0.043(12) 0.003(10) C2 0.070(14) 0.051(13) 0.077(17) -0.011(11) 0.028(12) 0.016(10) C3 0.087(17) 0.038(12) 0.10(2) -0.024(11) 0.029(15) -0.001(11) C4 0.076(14) 0.038(12) 0.098(19) -0.018(11) 0.054(13) -0.005(10) C5 0.096(17) 0.022(10) 0.093(19) -0.008(10) 0.044(15) -0.011(10) C6 0.071(14) 0.052(13) 0.073(17) -0.026(11) 0.020(12) -0.032(11) C7 0.049(12) 0.057(12) 0.065(16) -0.001(11) 0.014(10) -0.006(10) C8 0.035(11) 0.078(14) 0.087(18) 0.011(13) 0.029(11) -0.015(10) C9 0.039(11) 0.049(12) 0.067(16) -0.019(10) 0.008(10) -0.013(9) C10 0.017(9) 0.116(19) 0.076(16) -0.007(13) 0.012(9) 0.026(10) C11 0.031(9) 0.037(10) 0.060(15) -0.006(9) 0.017(9) -0.007(7) C12 0.038(10) 0.034(9) 0.057(14) -0.007(9) 0.019(9) 0.011(8) C13 0.051(10) 0.027(9) 0.039(12) 0.007(8) 0.029(9) 0.010(8) C14 0.023(8) 0.048(10) 0.050(13) 0.000(9) 0.009(8) 0.001(8) C15 0.036(10) 0.047(11) 0.056(14) 0.011(10) 0.013(9) 0.005(8) C16 0.035(10) 0.048(10) 0.036(13) -0.009(9) 0.011(9) 0.001(8) C17 0.052(11) 0.057(12) 0.058(16) 0.006(11) 0.016(10) 0.018(10) C18 0.036(10) 0.043(10) 0.063(15) 0.015(10) 0.014(9) 0.007(8) C19 0.031(9) 0.043(10) 0.056(14) 0.009(9) 0.014(9) 0.011(8) C20 0.049(12) 0.057(12) 0.085(18) 0.030(12) 0.026(12) 0.012(10) C21 0.039(11) 0.055(12) 0.091(18) 0.020(12) 0.021(11) -0.001(9) C22 0.060(13) 0.046(11) 0.066(16) 0.008(10) 0.023(11) 0.011(9) C23 0.039(10) 0.041(10) 0.062(15) 0.013(10) 0.022(10) 0.004(8) C24 0.021(8) 0.051(11) 0.042(13) -0.004(9) 0.007(8) -0.004(7) C25 0.032(10) 0.052(11) 0.059(15) 0.015(10) -0.005(9) 0.005(9) C26 0.044(11) 0.033(10) 0.071(16) 0.017(10) 0.017(10) 0.000(8) C27 0.048(12) 0.037(11) 0.104(19) -0.018(11) 0.042(12) -0.019(9) C28 0.054(12) 0.036(10) 0.059(15) 0.004(9) 0.033(11) 0.004(8) C29 0.084(15) 0.035(11) 0.064(17) -0.013(10) 0.014(12) 0.024(10) C30 0.073(15) 0.054(14) 0.09(2) -0.026(12) 0.025(13) -0.002(11) C31 0.11(2) 0.044(12) 0.09(2) -0.044(13) 0.037(16) 0.011(13) C32 0.081(14) 0.039(10) 0.060(15) 0.000(11) 0.038(11) 0.028(11) C33 0.044(11) 0.052(11) 0.070(15) 0.000(11) 0.024(10) -0.014(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 Er1 O2 2.239(12) 3_767 ? Er1 O1 2.261(11) . ? Er1 O6 2.368(11) . ? Er1 O5 2.387(10) . ? Er1 O4 2.402(11) 3_667 ? Er1 O3 2.420(10) 3_667 ? Er1 N2 2.514(14) . ? Er1 N1 2.520(13) . ? Er1 C26 2.782(17) 3_667 ? N1 C1 1.328(19) . ? N1 C12 1.338(19) . ? N2 C10 1.323(18) . ? N2 C11 1.361(19) . ? N3 N4 1.220(18) . ? N3 C16 1.444(18) . ? N4 C20 1.47(2) . ? N5 N5 1.23(3) 3_677 ? N5 C32 1.42(2) . ? O1 C13 1.281(17) . ? O2 C13 1.280(18) . ? O2 Er1 2.239(11) 3_767 ? O3 C26 1.265(18) . ? O3 Er1 2.421(10) 3_667 ? O4 C26 1.273(18) . ? O4 Er1 2.402(11) 3_667 ? O5 C27 1.26(2) . ? O6 C27 1.30(2) . ? C1 C2 1.42(2) . ? C1 H1 0.9300 . ? C2 C3 1.38(3) . ? C2 H2 0.9300 . ? C3 C4 1.38(2) . ? C3 H3 0.9300 . ? C4 C12 1.41(2) . ? C4 C5 1.46(3) . ? C5 C6 1.28(2) . ? C5 H5 0.9300 . ? C6 C7 1.46(2) . ? C6 H6 0.9300 . ? C7 C8 1.41(2) . ? C7 C11 1.44(2) . ? C8 C9 1.40(2) . ? C8 H8 0.9300 . ? C9 C10 1.40(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.444(19) . ? C13 C14 1.46(2) . ? C14 C19 1.35(2) . ? C14 C15 1.438(19) . ? C15 C16 1.38(2) . ? C15 H15 0.9300 . ? C16 C17 1.44(2) . ? C17 C18 1.36(2) . ? C17 H17 0.9300 . ? C18 C19 1.40(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C25 1.34(2) . ? C20 C21 1.42(2) . ? C21 C22 1.38(2) . ? C21 H21 0.9300 . ? C22 C23 1.36(2) . ? C22 H22 0.9300 . ? C23 C24 1.36(2) . ? C23 H23 0.9300 . ? C24 C25 1.441(19) . ? C24 C26 1.51(2) . ? C25 H25 0.9300 . ? C26 Er1 2.782(17) 3_667 ? C27 C28 1.48(2) . ? C28 C29 1.37(2) . ? C28 C33 1.40(2) . ? C29 C30 1.37(2) . ? C29 H29 0.9300 . ? C30 C31 1.39(3) . ? C30 H30 0.9300 . ? C31 C32 1.38(3) . ? C31 H31 0.9300 . ? C32 C33 1.43(2) . ? C33 H33 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 O2 Er1 O1 89.7(4) 3_767 . ? O2 Er1 O6 81.1(4) 3_767 . ? O1 Er1 O6 84.6(4) . . ? O2 Er1 O5 135.5(4) 3_767 . ? O1 Er1 O5 79.8(4) . . ? O6 Er1 O5 55.0(4) . . ? O2 Er1 O4 77.6(4) 3_767 3_667 ? O1 Er1 O4 149.8(4) . 3_667 ? O6 Er1 O4 119.6(4) . 3_667 ? O5 Er1 O4 128.0(3) . 3_667 ? O2 Er1 O3 110.1(4) 3_767 3_667 ? O1 Er1 O3 154.5(4) . 3_667 ? O6 Er1 O3 82.9(4) . 3_667 ? O5 Er1 O3 74.8(4) . 3_667 ? O4 Er1 O3 54.1(4) 3_667 3_667 ? O2 Er1 N2 148.5(4) 3_767 . ? O1 Er1 N2 95.0(4) . . ? O6 Er1 N2 130.4(4) . . ? O5 Er1 N2 76.0(4) . . ? O4 Er1 N2 82.9(4) 3_667 . ? O3 Er1 N2 76.7(4) 3_667 . ? O2 Er1 N1 85.6(4) 3_767 . ? O1 Er1 N1 78.1(4) . . ? O6 Er1 N1 158.2(4) . . ? O5 Er1 N1 132.7(5) . . ? O4 Er1 N1 73.7(4) 3_667 . ? O3 Er1 N1 118.0(4) 3_667 . ? N2 Er1 N1 65.1(4) . . ? O2 Er1 C26 95.2(5) 3_767 3_667 ? O1 Er1 C26 171.6(5) . 3_667 ? O6 Er1 C26 102.9(5) . 3_667 ? O5 Er1 C26 101.2(4) . 3_667 ? O4 Er1 C26 27.2(4) 3_667 3_667 ? O3 Er1 C26 27.0(4) 3_667 3_667 ? N2 Er1 C26 77.3(5) . 3_667 ? N1 Er1 C26 95.4(5) . 3_667 ? C1 N1 C12 118.1(15) . . ? C1 N1 Er1 122.9(13) . . ? C12 N1 Er1 118.8(10) . . ? C10 N2 C11 118.0(16) . . ? C10 N2 Er1 122.4(13) . . ? C11 N2 Er1 119.4(10) . . ? N4 N3 C16 113.0(14) . . ? N3 N4 C20 113.7(15) . . ? N5 N5 C32 114(2) 3_677 . ? C13 O1 Er1 141.2(11) . . ? C13 O2 Er1 162.2(10) . 3_767 ? C26 O3 Er1 92.6(10) . 3_667 ? C26 O4 Er1 93.3(10) . 3_667 ? C27 O5 Er1 92.8(11) . . ? C27 O6 Er1 92.5(10) . . ? N1 C1 C2 121.8(18) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.9(17) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 118.3(17) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C3 C4 C12 118.3(18) . . ? C3 C4 C5 122.5(17) . . ? C12 C4 C5 119.2(16) . . ? C6 C5 C4 123.3(17) . . ? C6 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C5 C6 C7 121.4(18) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C11 116.2(17) . . ? C8 C7 C6 126.4(18) . . ? C11 C7 C6 117.3(16) . . ? C9 C8 C7 122.2(18) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 114.8(17) . . ? C10 C9 H9 122.6 . . ? C8 C9 H9 122.6 . . ? N2 C10 C9 126(2) . . ? N2 C10 H10 116.8 . . ? C9 C10 H10 116.8 . . ? N2 C11 C7 122.0(15) . . ? N2 C11 C12 116.7(14) . . ? C7 C11 C12 121.3(15) . . ? N1 C12 C4 123.5(15) . . ? N1 C12 C11 119.0(14) . . ? C4 C12 C11 117.5(16) . . ? O2 C13 O1 121.9(15) . . ? O2 C13 C14 116.7(13) . . ? O1 C13 C14 121.4(15) . . ? C19 C14 C15 121.1(16) . . ? C19 C14 C13 121.1(14) . . ? C15 C14 C13 117.7(14) . . ? C16 C15 C14 118.4(15) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C15 C16 C17 120.0(15) . . ? C15 C16 N3 124.4(15) . . ? C17 C16 N3 115.6(15) . . ? C18 C17 C16 118.5(17) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 121.9(16) . . ? C17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C14 C19 C18 119.6(15) . . ? C14 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C25 C20 C21 120.0(17) . . ? C25 C20 N4 115.8(17) . . ? C21 C20 N4 123.8(16) . . ? C22 C21 C20 118.2(17) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? C23 C22 C21 122.4(17) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C22 C23 C24 120.0(15) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 118.8(15) . . ? C23 C24 C26 121.4(14) . . ? C25 C24 C26 119.4(15) . . ? C20 C25 C24 120.5(16) . . ? C20 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? O3 C26 O4 119.7(15) . . ? O3 C26 C24 121.0(15) . . ? O4 C26 C24 119.3(14) . . ? O3 C26 Er1 60.4(8) . 3_667 ? O4 C26 Er1 59.5(8) . 3_667 ? C24 C26 Er1 174.2(13) . 3_667 ? O5 C27 O6 118.6(15) . . ? O5 C27 C28 121.5(18) . . ? O6 C27 C28 119.6(17) . . ? C29 C28 C33 120.2(16) . . ? C29 C28 C27 121.5(17) . . ? C33 C28 C27 117.8(17) . . ? C30 C29 C28 119.4(19) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C29 C30 C31 121(2) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 121.4(16) . . ? C32 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? C31 C32 N5 127.2(16) . . ? C31 C32 C33 116.5(17) . . ? N5 C32 C33 115.8(18) . . ? C28 C33 C32 120.7(17) . . ? C28 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? 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 O2 Er1 N1 C1 -14.7(14) 3_767 . . . ? O1 Er1 N1 C1 76.0(14) . . . . ? O6 Er1 N1 C1 38(2) . . . . ? O5 Er1 N1 C1 139.9(13) . . . . ? O4 Er1 N1 C1 -93.0(15) 3_667 . . . ? O3 Er1 N1 C1 -125.1(14) 3_667 . . . ? N2 Er1 N1 C1 177.3(16) . . . . ? C26 Er1 N1 C1 -109.5(15) 3_667 . . . ? O2 Er1 N1 C12 160.1(13) 3_767 . . . ? O1 Er1 N1 C12 -109.2(13) . . . . ? O6 Er1 N1 C12 -147.4(12) . . . . ? O5 Er1 N1 C12 -45.3(15) . . . . ? O4 Er1 N1 C12 81.8(13) 3_667 . . . ? O3 Er1 N1 C12 49.7(14) 3_667 . . . ? N2 Er1 N1 C12 -7.9(12) . . . . ? C26 Er1 N1 C12 65.3(13) 3_667 . . . ? O2 Er1 N2 C10 159.9(13) 3_767 . . . ? O1 Er1 N2 C10 -102.4(14) . . . . ? O6 Er1 N2 C10 -15.3(16) . . . . ? O5 Er1 N2 C10 -24.2(14) . . . . ? O4 Er1 N2 C10 107.9(14) 3_667 . . . ? O3 Er1 N2 C10 53.2(14) 3_667 . . . ? N1 Er1 N2 C10 -176.8(15) . . . . ? C26 Er1 N2 C10 80.9(14) 3_667 . . . ? O2 Er1 N2 C11 -15.1(17) 3_767 . . . ? O1 Er1 N2 C11 82.6(12) . . . . ? O6 Er1 N2 C11 169.7(11) . . . . ? O5 Er1 N2 C11 160.8(13) . . . . ? O4 Er1 N2 C11 -67.1(12) 3_667 . . . ? O3 Er1 N2 C11 -121.9(13) 3_667 . . . ? N1 Er1 N2 C11 8.1(12) . . . . ? C26 Er1 N2 C11 -94.1(13) 3_667 . . . ? C16 N3 N4 C20 173.2(15) . . . . ? O2 Er1 O1 C13 -66.4(16) 3_767 . . . ? O6 Er1 O1 C13 14.7(15) . . . . ? O5 Er1 O1 C13 70.1(16) . . . . ? O4 Er1 O1 C13 -130.7(15) 3_667 . . . ? O3 Er1 O1 C13 75.7(19) 3_667 . . . ? N2 Er1 O1 C13 144.9(16) . . . . ? N1 Er1 O1 C13 -152.0(16) . . . . ? O2 Er1 O5 C27 -17.4(13) 3_767 . . . ? O1 Er1 O5 C27 -96.5(11) . . . . ? O6 Er1 O5 C27 -6.0(10) . . . . ? O4 Er1 O5 C27 96.6(11) 3_667 . . . ? O3 Er1 O5 C27 86.0(10) 3_667 . . . ? N2 Er1 O5 C27 165.7(11) . . . . ? N1 Er1 O5 C27 -159.7(10) . . . . ? C26 Er1 O5 C27 92.0(11) 3_667 . . . ? O2 Er1 O6 C27 177.8(11) 3_767 . . . ? O1 Er1 O6 C27 87.2(11) . . . . ? O5 Er1 O6 C27 5.8(10) . . . . ? O4 Er1 O6 C27 -112.0(10) 3_667 . . . ? O3 Er1 O6 C27 -70.6(11) 3_667 . . . ? N2 Er1 O6 C27 -4.8(13) . . . . ? N1 Er1 O6 C27 124.6(14) . . . . ? C26 Er1 O6 C27 -88.9(11) 3_667 . . . ? C12 N1 C1 C2 -3(3) . . . . ? Er1 N1 C1 C2 172.2(15) . . . . ? N1 C1 C2 C3 0(3) . . . . ? C1 C2 C3 C4 3(3) . . . . ? C2 C3 C4 C12 -5(3) . . . . ? C2 C3 C4 C5 177.7(19) . . . . ? C3 C4 C5 C6 -179(2) . . . . ? C12 C4 C5 C6 4(3) . . . . ? C4 C5 C6 C7 -5(3) . . . . ? C5 C6 C7 C8 179(2) . . . . ? C5 C6 C7 C11 3(3) . . . . ? C11 C7 C8 C9 -3(3) . . . . ? C6 C7 C8 C9 -179.5(19) . . . . ? C7 C8 C9 C10 6(3) . . . . ? C11 N2 C10 C9 4(3) . . . . ? Er1 N2 C10 C9 -170.7(15) . . . . ? C8 C9 C10 N2 -7(3) . . . . ? C10 N2 C11 C7 -1(3) . . . . ? Er1 N2 C11 C7 174.0(13) . . . . ? C10 N2 C11 C12 176.8(16) . . . . ? Er1 N2 C11 C12 -8(2) . . . . ? C8 C7 C11 N2 1(3) . . . . ? C6 C7 C11 N2 177.3(17) . . . . ? C8 C7 C11 C12 -177.2(16) . . . . ? C6 C7 C11 C12 -1(3) . . . . ? C1 N1 C12 C4 1(3) . . . . ? Er1 N1 C12 C4 -174.0(14) . . . . ? C1 N1 C12 C11 -177.5(16) . . . . ? Er1 N1 C12 C11 7(2) . . . . ? C3 C4 C12 N1 3(3) . . . . ? C5 C4 C12 N1 -179.6(17) . . . . ? C3 C4 C12 C11 -178.7(18) . . . . ? C5 C4 C12 C11 -1(3) . . . . ? N2 C11 C12 N1 0(2) . . . . ? C7 C11 C12 N1 178.4(16) . . . . ? N2 C11 C12 C4 -178.4(16) . . . . ? C7 C11 C12 C4 0(3) . . . . ? Er1 O2 C13 O1 17(5) 3_767 . . . ? Er1 O2 C13 C14 -165(3) 3_767 . . . ? Er1 O1 C13 O2 66(2) . . . . ? Er1 O1 C13 C14 -112.2(18) . . . . ? O2 C13 C14 C19 13(2) . . . . ? O1 C13 C14 C19 -169.1(16) . . . . ? O2 C13 C14 C15 -165.0(14) . . . . ? O1 C13 C14 C15 13(2) . . . . ? C19 C14 C15 C16 -3(3) . . . . ? C13 C14 C15 C16 174.9(15) . . . . ? C14 C15 C16 C17 6(3) . . . . ? C14 C15 C16 N3 -171.7(15) . . . . ? N4 N3 C16 C15 2(2) . . . . ? N4 N3 C16 C17 -175.9(17) . . . . ? C15 C16 C17 C18 -7(3) . . . . ? N3 C16 C17 C18 170.8(15) . . . . ? C16 C17 C18 C19 5(3) . . . . ? C15 C14 C19 C18 1(3) . . . . ? C13 C14 C19 C18 -176.8(15) . . . . ? C17 C18 C19 C14 -2(3) . . . . ? N3 N4 C20 C25 -173.1(19) . . . . ? N3 N4 C20 C21 0(3) . . . . ? C25 C20 C21 C22 1(3) . . . . ? N4 C20 C21 C22 -171.2(19) . . . . ? C20 C21 C22 C23 -1(3) . . . . ? C21 C22 C23 C24 -1(3) . . . . ? C22 C23 C24 C25 3(3) . . . . ? C22 C23 C24 C26 175.7(17) . . . . ? C21 C20 C25 C24 1(3) . . . . ? N4 C20 C25 C24 173.9(16) . . . . ? C23 C24 C25 C20 -3(3) . . . . ? C26 C24 C25 C20 -176.0(18) . . . . ? Er1 O3 C26 O4 -4.9(18) 3_667 . . . ? Er1 O3 C26 C24 173.5(15) 3_667 . . . ? Er1 O4 C26 O3 5.0(18) 3_667 . . . ? Er1 O4 C26 C24 -173.4(14) 3_667 . . . ? C23 C24 C26 O3 159.8(17) . . . . ? C25 C24 C26 O3 -27(3) . . . . ? C23 C24 C26 O4 -22(3) . . . . ? C25 C24 C26 O4 151.1(17) . . . . ? Er1 O5 C27 O6 10.3(17) . . . . ? Er1 O5 C27 C28 -176.4(14) . . . . ? Er1 O6 C27 O5 -10.4(18) . . . . ? Er1 O6 C27 C28 176.2(14) . . . . ? O5 C27 C28 C29 -178.9(18) . . . . ? O6 C27 C28 C29 -6(3) . . . . ? O5 C27 C28 C33 9(3) . . . . ? O6 C27 C28 C33 -177.4(16) . . . . ? C33 C28 C29 C30 -5(3) . . . . ? C27 C28 C29 C30 -176.6(18) . . . . ? C28 C29 C30 C31 10(3) . . . . ? C29 C30 C31 C32 -9(4) . . . . ? C30 C31 C32 N5 176(2) . . . . ? C30 C31 C32 C33 4(3) . . . . ? N5 N5 C32 C31 -5(3) 3_677 . . . ? N5 N5 C32 C33 168(2) 3_677 . . . ? C29 C28 C33 C32 0(3) . . . . ? C27 C28 C33 C32 171.5(16) . . . . ? C31 C32 C33 C28 1(3) . . . . ? N5 C32 C33 C28 -172.3(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.992 _refine_diff_density_min -1.595 _refine_diff_density_rms 0.195 # Attachment 'Compound 12.cif' data_xb1108 _database_code_depnum_ccdc_archive 'CCDC 651809' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 Ba N2 O4' _chemical_formula_weight 405.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ba Ba -0.3244 2.2819 '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 7.786(3) _cell_length_b 10.464(4) _cell_length_c 31.574(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2572.3(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1961 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.30 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 3.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5562 _exptl_absorpt_correction_T_max 0.8143 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9069 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0745 _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 -23 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2261 _reflns_number_gt 1620 _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^)+(0.0000P)^2^+480.0000P] 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 0.00042(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2261 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.1096 _refine_ls_wR_factor_ref 0.2815 _refine_ls_wR_factor_gt 0.2672 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Ba1 Ba 0.96824(18) 0.20015(13) 0.51415(5) 0.0251(5) Uani 1 1 d . . . N1 N 0.627(3) 0.109(2) 0.2787(7) 0.038(6) Uani 1 1 d . . . N2 N 0.594(3) 0.021(2) 0.2536(8) 0.038(6) Uani 1 1 d . . . O1 O 0.6754(19) 0.0916(15) 0.4807(6) 0.026(4) Uani 1 1 d . . . O2 O 0.6945(19) -0.1192(13) 0.4642(5) 0.021(4) Uani 1 1 d . . . O3 O 0.548(2) 0.0291(14) 0.0521(6) 0.027(4) Uani 1 1 d . . . O4 O 0.697(2) 0.2092(17) 0.0608(5) 0.032(4) Uani 1 1 d . . . C1 C 0.661(3) 0.000(2) 0.4547(9) 0.024(6) Uani 1 1 d . . . C2 C 0.638(3) 0.029(2) 0.4095(8) 0.022(5) Uani 1 1 d . . . C3 C 0.561(3) -0.060(2) 0.3818(8) 0.026(6) Uani 1 1 d . . . H3 H 0.5163 -0.1357 0.3926 0.031 Uiso 1 1 calc R . . C4 C 0.553(4) -0.037(2) 0.3389(8) 0.034(6) Uani 1 1 d . . . H4 H 0.5030 -0.0969 0.3209 0.041 Uiso 1 1 calc R . . C5 C 0.620(4) 0.079(2) 0.3222(8) 0.032(6) Uani 1 1 d . . . C6 C 0.685(4) 0.171(2) 0.3501(9) 0.034(7) Uani 1 1 d . . . H6 H 0.7216 0.2494 0.3397 0.041 Uiso 1 1 calc R . . C7 C 0.696(3) 0.147(2) 0.3931(8) 0.023(5) Uani 1 1 d . . . H7 H 0.7410 0.2080 0.4112 0.027 Uiso 1 1 calc R . . C8 C 0.629(3) 0.106(2) 0.0751(8) 0.022(5) Uani 1 1 d . . . C9 C 0.629(3) 0.086(2) 0.1222(8) 0.021(5) Uani 1 1 d . . . C10 C 0.550(3) -0.026(2) 0.1390(8) 0.025(5) Uani 1 1 d . . . H10 H 0.5044 -0.0875 0.1211 0.030 Uiso 1 1 calc R . . C11 C 0.542(4) -0.041(2) 0.1820(9) 0.033(6) Uani 1 1 d . . . H11 H 0.4901 -0.1142 0.1928 0.039 Uiso 1 1 calc R . . C12 C 0.607(3) 0.049(3) 0.2103(9) 0.033(6) Uani 1 1 d . . . C13 C 0.691(3) 0.160(2) 0.1936(9) 0.031(6) Uani 1 1 d . . . H13 H 0.7388 0.2204 0.2116 0.037 Uiso 1 1 calc R . . C14 C 0.698(3) 0.175(2) 0.1504(9) 0.027(6) Uani 1 1 d . . . H14 H 0.7513 0.2471 0.1395 0.032 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 Ba1 0.0292(8) 0.0115(6) 0.0345(9) -0.0001(7) 0.0005(7) -0.0002(6) N1 0.048(15) 0.024(11) 0.041(14) -0.003(11) 0.001(12) 0.009(11) N2 0.034(13) 0.033(12) 0.047(15) 0.004(12) -0.006(12) 0.007(11) O1 0.017(8) 0.019(8) 0.042(11) -0.011(9) -0.009(8) 0.006(7) O2 0.016(8) 0.004(6) 0.043(10) 0.005(7) -0.003(7) 0.004(6) O3 0.019(9) 0.011(8) 0.052(11) 0.000(8) -0.004(8) 0.002(7) O4 0.032(10) 0.029(9) 0.035(10) -0.007(9) 0.010(8) -0.003(9) C1 0.019(12) 0.013(10) 0.041(15) 0.005(11) -0.003(11) 0.005(9) C2 0.014(11) 0.012(11) 0.040(15) 0.007(11) 0.001(10) 0.002(9) C3 0.041(16) 0.001(10) 0.036(15) -0.002(10) -0.005(13) 0.001(10) C4 0.044(17) 0.023(13) 0.035(15) 0.005(12) -0.011(13) -0.003(12) C5 0.047(17) 0.015(12) 0.032(15) 0.007(11) 0.007(13) 0.006(12) C6 0.057(18) 0.003(10) 0.042(17) 0.001(11) 0.003(14) -0.005(11) C7 0.021(12) 0.018(11) 0.030(14) 0.009(11) -0.002(11) 0.001(10) C8 0.018(12) 0.006(10) 0.040(15) 0.009(11) -0.001(11) -0.001(9) C9 0.021(12) 0.008(10) 0.034(14) -0.008(10) 0.001(11) 0.000(10) C10 0.022(13) 0.014(11) 0.038(15) 0.007(11) 0.002(12) -0.003(10) C11 0.033(15) 0.018(12) 0.048(17) 0.003(12) -0.011(14) 0.001(11) C12 0.030(14) 0.028(13) 0.041(17) 0.005(13) 0.000(13) 0.001(12) C13 0.034(15) 0.016(11) 0.043(17) 0.000(12) -0.008(13) -0.013(11) C14 0.025(13) 0.004(10) 0.051(18) -0.001(11) -0.013(12) -0.004(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 Ba1 O3 2.684(16) 2_655 ? Ba1 O1 2.715(15) 4_556 ? Ba1 O4 2.745(16) 7_566 ? Ba1 O1 2.757(15) . ? Ba1 O2 2.769(15) 8_765 ? Ba1 O3 2.822(17) 6_656 ? Ba1 O2 2.843(15) 5_756 ? Ba1 O4 2.963(18) 6_656 ? Ba1 C8 3.24(2) 6_656 ? Ba1 Ba1 4.1281(16) 4_556 ? Ba1 Ba1 4.1281(15) 4_456 ? Ba1 Ba1 4.311(3) 5_756 ? N1 N2 1.24(3) . ? N1 C5 1.41(3) . ? N2 C12 1.40(4) . ? O1 C1 1.27(3) . ? O1 Ba1 2.715(15) 4_456 ? O2 C1 1.31(3) . ? O2 Ba1 2.769(15) 8_755 ? O2 Ba1 2.843(14) 5_756 ? O3 C8 1.26(3) . ? O3 Ba1 2.684(15) 2_654 ? O3 Ba1 2.822(17) 6_556 ? O4 C8 1.28(3) . ? O4 Ba1 2.745(16) 7_565 ? O4 Ba1 2.963(18) 6_556 ? C1 C2 1.47(3) . ? C2 C7 1.41(3) . ? C2 C3 1.41(3) . ? C3 C4 1.38(3) . ? C3 H3 0.9300 . ? C4 C5 1.42(3) . ? C4 H4 0.9300 . ? C5 C6 1.40(4) . ? C6 C7 1.38(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.50(3) . ? C8 Ba1 3.24(2) 6_556 ? C9 C14 1.39(3) . ? C9 C10 1.43(3) . ? C10 C11 1.37(4) . ? C10 H10 0.9300 . ? C11 C12 1.39(4) . ? C11 H11 0.9300 . ? C12 C13 1.43(3) . ? C13 C14 1.37(4) . ? 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 O3 Ba1 O1 135.9(5) 2_655 4_556 ? O3 Ba1 O4 91.9(5) 2_655 7_566 ? O1 Ba1 O4 98.5(5) 4_556 7_566 ? O3 Ba1 O1 76.3(5) 2_655 . ? O1 Ba1 O1 147.6(3) 4_556 . ? O4 Ba1 O1 73.2(5) 7_566 . ? O3 Ba1 O2 147.4(5) 2_655 8_765 ? O1 Ba1 O2 76.0(5) 4_556 8_765 ? O4 Ba1 O2 73.6(5) 7_566 8_765 ? O1 Ba1 O2 71.6(4) . 8_765 ? O3 Ba1 O3 76.9(6) 2_655 6_656 ? O1 Ba1 O3 115.0(5) 4_556 6_656 ? O4 Ba1 O3 141.9(5) 7_566 6_656 ? O1 Ba1 O3 68.7(5) . 6_656 ? O2 Ba1 O3 96.4(5) 8_765 6_656 ? O3 Ba1 O2 70.7(5) 2_655 5_756 ? O1 Ba1 O2 71.1(4) 4_556 5_756 ? O4 Ba1 O2 133.2(5) 7_566 5_756 ? O1 Ba1 O2 137.2(4) . 5_756 ? O2 Ba1 O2 139.7(4) 8_765 5_756 ? O3 Ba1 O2 77.7(5) 6_656 5_756 ? O3 Ba1 O4 114.4(5) 2_655 6_656 ? O1 Ba1 O4 70.4(5) 4_556 6_656 ? O4 Ba1 O4 151.7(3) 7_566 6_656 ? O1 Ba1 O4 101.8(5) . 6_656 ? O2 Ba1 O4 78.3(5) 8_765 6_656 ? O3 Ba1 O4 45.3(5) 6_656 6_656 ? O2 Ba1 O4 69.3(5) 5_756 6_656 ? O3 Ba1 C8 97.8(5) 2_655 6_656 ? O1 Ba1 C8 93.7(5) 4_556 6_656 ? O4 Ba1 C8 150.5(6) 7_566 6_656 ? O1 Ba1 C8 82.1(5) . 6_656 ? O2 Ba1 C8 83.5(5) 8_765 6_656 ? O3 Ba1 C8 22.6(5) 6_656 6_656 ? O2 Ba1 C8 76.2(5) 5_756 6_656 ? O4 Ba1 C8 23.3(5) 6_656 6_656 ? O3 Ba1 Ba1 111.5(3) 2_655 4_556 ? O1 Ba1 Ba1 41.4(3) 4_556 4_556 ? O4 Ba1 Ba1 139.0(4) 7_566 4_556 ? O1 Ba1 Ba1 143.2(4) . 4_556 ? O2 Ba1 Ba1 97.8(3) 8_765 4_556 ? O3 Ba1 Ba1 78.0(3) 6_656 4_556 ? O2 Ba1 Ba1 42.0(3) 5_756 4_556 ? O4 Ba1 Ba1 41.6(3) 6_656 4_556 ? C8 Ba1 Ba1 61.5(4) 6_656 4_556 ? O3 Ba1 Ba1 106.1(4) 2_655 4_456 ? O1 Ba1 Ba1 111.7(3) 4_556 4_456 ? O4 Ba1 Ba1 45.8(4) 7_566 4_456 ? O1 Ba1 Ba1 40.7(3) . 4_456 ? O2 Ba1 Ba1 43.3(3) 8_765 4_456 ? O3 Ba1 Ba1 102.0(3) 6_656 4_456 ? O2 Ba1 Ba1 176.9(3) 5_756 4_456 ? O4 Ba1 Ba1 112.7(3) 6_656 4_456 ? C8 Ba1 Ba1 104.6(4) 6_656 4_456 ? Ba1 Ba1 Ba1 141.13(8) 4_556 4_456 ? O3 Ba1 Ba1 39.6(4) 2_655 5_756 ? O1 Ba1 Ba1 136.4(3) 4_556 5_756 ? O4 Ba1 Ba1 122.4(4) 7_566 5_756 ? O1 Ba1 Ba1 67.4(3) . 5_756 ? O2 Ba1 Ba1 126.7(3) 8_765 5_756 ? O3 Ba1 Ba1 37.3(3) 6_656 5_756 ? O2 Ba1 Ba1 69.8(3) 5_756 5_756 ? O4 Ba1 Ba1 78.3(4) 6_656 5_756 ? C8 Ba1 Ba1 58.7(4) 6_656 5_756 ? Ba1 Ba1 Ba1 95.31(5) 4_556 5_756 ? Ba1 Ba1 Ba1 107.99(6) 4_456 5_756 ? N2 N1 C5 116(2) . . ? N1 N2 C12 117(2) . . ? C1 O1 Ba1 126.3(14) . 4_456 ? C1 O1 Ba1 129.2(14) . . ? Ba1 O1 Ba1 97.9(5) 4_456 . ? C1 O2 Ba1 133.6(15) . 8_755 ? C1 O2 Ba1 121.5(14) . 5_756 ? Ba1 O2 Ba1 94.7(4) 8_755 5_756 ? C8 O3 Ba1 148.9(14) . 2_654 ? C8 O3 Ba1 97.6(13) . 6_556 ? Ba1 O3 Ba1 103.1(6) 2_654 6_556 ? C8 O4 Ba1 142.9(15) . 7_565 ? C8 O4 Ba1 90.4(14) . 6_556 ? Ba1 O4 Ba1 92.6(5) 7_565 6_556 ? O1 C1 O2 124(2) . . ? O1 C1 C2 119(2) . . ? O2 C1 C2 116(2) . . ? C7 C2 C3 119(2) . . ? C7 C2 C1 120(2) . . ? C3 C2 C1 121(2) . . ? C4 C3 C2 121(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 N1 116(2) . . ? C6 C5 C4 119(2) . . ? N1 C5 C4 124(2) . . ? C7 C6 C5 121(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 120(2) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O3 C8 O4 123(2) . . ? O3 C8 C9 119(2) . . ? O4 C8 C9 118(2) . . ? O3 C8 Ba1 59.8(12) . 6_556 ? O4 C8 Ba1 66.3(13) . 6_556 ? C9 C8 Ba1 154.8(15) . 6_556 ? C14 C9 C10 118(2) . . ? C14 C9 C8 123(2) . . ? C10 C9 C8 119(2) . . ? C11 C10 C9 119(2) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 123(2) . . ? C10 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C11 C12 N2 117(2) . . ? C11 C12 C13 119(3) . . ? N2 C12 C13 124(3) . . ? C14 C13 C12 118(2) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C9 123(2) . . ? C13 C14 H14 118.5 . . ? C9 C14 H14 118.5 . . ? 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 C5 N1 N2 C12 -178(2) . . . . ? O3 Ba1 O1 C1 -71(2) 2_655 . . . ? O1 Ba1 O1 C1 113(2) 4_556 . . . ? O4 Ba1 O1 C1 -168(2) 7_566 . . . ? O2 Ba1 O1 C1 114(2) 8_765 . . . ? O3 Ba1 O1 C1 9.6(19) 6_656 . . . ? O2 Ba1 O1 C1 -31(2) 5_756 . . . ? O4 Ba1 O1 C1 41(2) 6_656 . . . ? C8 Ba1 O1 C1 29(2) 6_656 . . . ? Ba1 Ba1 O1 C1 36(2) 4_556 . . . ? Ba1 Ba1 O1 C1 152(2) 4_456 . . . ? Ba1 Ba1 O1 C1 -30.7(19) 5_756 . . . ? O3 Ba1 O1 Ba1 136.3(6) 2_655 . . 4_456 ? O1 Ba1 O1 Ba1 -39.2(8) 4_556 . . 4_456 ? O4 Ba1 O1 Ba1 40.0(5) 7_566 . . 4_456 ? O2 Ba1 O1 Ba1 -37.9(5) 8_765 . . 4_456 ? O3 Ba1 O1 Ba1 -142.7(7) 6_656 . . 4_456 ? O2 Ba1 O1 Ba1 176.6(5) 5_756 . . 4_456 ? O4 Ba1 O1 Ba1 -111.2(5) 6_656 . . 4_456 ? C8 Ba1 O1 Ba1 -123.7(6) 6_656 . . 4_456 ? Ba1 Ba1 O1 Ba1 -116.0(4) 4_556 . . 4_456 ? Ba1 Ba1 O1 Ba1 177.0(6) 5_756 . . 4_456 ? Ba1 O1 C1 O2 -143.8(18) 4_456 . . . ? Ba1 O1 C1 O2 71(3) . . . . ? Ba1 O1 C1 C2 49(3) 4_456 . . . ? Ba1 O1 C1 C2 -97(2) . . . . ? Ba1 O2 C1 O1 71(3) 8_755 . . . ? Ba1 O2 C1 O1 -65(3) 5_756 . . . ? Ba1 O2 C1 C2 -121(2) 8_755 . . . ? Ba1 O2 C1 C2 103(2) 5_756 . . . ? O1 C1 C2 C7 24(3) . . . . ? O2 C1 C2 C7 -145(2) . . . . ? O1 C1 C2 C3 -157(2) . . . . ? O2 C1 C2 C3 35(3) . . . . ? C7 C2 C3 C4 4(4) . . . . ? C1 C2 C3 C4 -175(2) . . . . ? C2 C3 C4 C5 -1(4) . . . . ? N2 N1 C5 C6 169(3) . . . . ? N2 N1 C5 C4 -10(4) . . . . ? C3 C4 C5 C6 -4(4) . . . . ? C3 C4 C5 N1 176(3) . . . . ? N1 C5 C6 C7 -175(2) . . . . ? C4 C5 C6 C7 4(4) . . . . ? C5 C6 C7 C2 -1(4) . . . . ? C3 C2 C7 C6 -3(4) . . . . ? C1 C2 C7 C6 176(2) . . . . ? Ba1 O3 C8 O4 110(3) 2_654 . . . ? Ba1 O3 C8 O4 -21(2) 6_556 . . . ? Ba1 O3 C8 C9 -78(4) 2_654 . . . ? Ba1 O3 C8 C9 150.9(18) 6_556 . . . ? Ba1 O3 C8 Ba1 131(3) 2_654 . . 6_556 ? Ba1 O4 C8 O3 -75(3) 7_565 . . . ? Ba1 O4 C8 O3 20(2) 6_556 . . . ? Ba1 O4 C8 C9 113(3) 7_565 . . . ? Ba1 O4 C8 C9 -152.3(18) 6_556 . . . ? Ba1 O4 C8 Ba1 -95(2) 7_565 . . 6_556 ? O3 C8 C9 C14 -172(2) . . . . ? O4 C8 C9 C14 0(3) . . . . ? Ba1 C8 C9 C14 -92(4) 6_556 . . . ? O3 C8 C9 C10 5(3) . . . . ? O4 C8 C9 C10 178(2) . . . . ? Ba1 C8 C9 C10 85(4) 6_556 . . . ? C14 C9 C10 C11 1(3) . . . . ? C8 C9 C10 C11 -177(2) . . . . ? C9 C10 C11 C12 0(4) . . . . ? C10 C11 C12 N2 -179(2) . . . . ? C10 C11 C12 C13 -2(4) . . . . ? N1 N2 C12 C11 -169(3) . . . . ? N1 N2 C12 C13 14(4) . . . . ? C11 C12 C13 C14 2(4) . . . . ? N2 C12 C13 C14 179(2) . . . . ? C12 C13 C14 C9 -1(4) . . . . ? C10 C9 C14 C13 -1(4) . . . . ? C8 C9 C14 C13 177(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 3.130 _refine_diff_density_min -3.132 _refine_diff_density_rms 0.312