# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yu-Bin Dong' _publ_contact_author_email yubindong@yahoo.com _publ_author_name 'Yu-Bin Dong' data_1 _database_code_depnum_ccdc_archive 'CCDC 853356' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N4 O8 Zn' _chemical_formula_weight 633.90 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' 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 8.388(2) _cell_length_b 9.738(2) _cell_length_c 9.873(3) _cell_angle_alpha 108.791(4) _cell_angle_beta 104.892(3) _cell_angle_gamma 107.590(3) _cell_volume 669.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1248 _cell_measurement_theta_min 2.369 _cell_measurement_theta_max 25.821 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 0.980 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8511 _exptl_absorpt_correction_T_max 0.8832 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 3538 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.48 _reflns_number_total 2452 _reflns_number_gt 2223 _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^)+(0.0596P)^2^+0.1691P] 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 2452 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8209(4) 0.2791(4) 1.2438(4) 0.0334(7) Uani 1 1 d . . . H1 H 0.9090 0.2650 1.3103 0.040 Uiso 1 1 calc R . . C2 C 0.7602(5) 0.3924(4) 1.3025(4) 0.0423(8) Uani 1 1 d . . . H2 H 0.8068 0.4547 1.4093 0.051 Uiso 1 1 calc R . . C3 C 0.6299(5) 0.4143(4) 1.2033(4) 0.0431(8) Uani 1 1 d . . . H3 H 0.5906 0.4920 1.2439 0.052 Uiso 1 1 calc R . . C4 C 0.5591(4) 0.3227(4) 1.0468(4) 0.0364(8) Uani 1 1 d . . . H4 H 0.4722 0.3391 0.9818 0.044 Uiso 1 1 calc R . . C5 C 0.6150(4) 0.2037(3) 0.9814(3) 0.0268(6) Uani 1 1 d . . . C6 C 0.7493(4) 0.1857(3) 1.0840(3) 0.0262(6) Uani 1 1 d . . . C7 C 0.7518(4) -0.0225(4) 0.8677(3) 0.0278(6) Uani 1 1 d . . . C8 C 0.6075(4) -0.0086(4) 0.7646(4) 0.0306(7) Uani 1 1 d . . . H8 H 0.5565 -0.0767 0.6590 0.037 Uiso 1 1 calc R . . C9 C 0.5448(4) 0.1009(4) 0.8183(3) 0.0274(6) Uani 1 1 d . . . C10 C 0.4006(4) 0.1201(4) 0.7049(3) 0.0300(7) Uani 1 1 d . . . C11 C 0.1031(4) -0.2657(4) 0.3360(4) 0.0326(7) Uani 1 1 d . . . H11 H 0.1715 -0.2401 0.4383 0.039 Uiso 1 1 calc R . . C12 C 0.1040(4) -0.3890(4) 0.2187(4) 0.0323(7) Uani 1 1 d . . . H12 H 0.1735 -0.4426 0.2434 0.039 Uiso 1 1 calc R . . C13 C 0.0023(4) -0.4338(3) 0.0641(3) 0.0259(6) Uani 1 1 d . . . C14 C -0.0937(4) -0.3442(4) 0.0397(3) 0.0311(7) Uani 1 1 d . . . H14 H -0.1641 -0.3676 -0.0613 0.037 Uiso 1 1 calc R . . C15 C -0.0860(4) -0.2220(4) 0.1623(3) 0.0301(7) Uani 1 1 d . . . H15 H -0.1510 -0.1639 0.1409 0.036 Uiso 1 1 calc R . . N1 N 0.0098(3) -0.1814(3) 0.3111(3) 0.0276(5) Uani 1 1 d . . . N2 N 0.8121(3) 0.0734(3) 1.0208(3) 0.0283(6) Uani 1 1 d . . . H2A H 0.8958 0.0643 1.0843 0.034 Uiso 1 1 calc R . . O1 O 0.2413(3) 0.0181(2) 0.6540(2) 0.0301(5) Uani 1 1 d . . . O2 O 0.4534(3) 0.2363(3) 0.6756(3) 0.0589(8) Uani 1 1 d . . . O3 O 0.8238(3) -0.1141(3) 0.8226(2) 0.0349(5) Uani 1 1 d . . . O4 O 0.1522(3) 0.1913(2) 0.4595(2) 0.0310(5) Uani 1 1 d . . . Zn1 Zn 0.0000 0.0000 0.5000 0.02510(18) Uani 1 2 d S . . H4A H 0.2605 0.2314 0.5281 0.038 Uiso 1 1 d R . . H4B H 0.1719 0.1752 0.3756 0.038 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0348(17) 0.0382(18) 0.0282(16) 0.0152(15) 0.0102(14) 0.0173(15) C2 0.047(2) 0.0389(19) 0.0316(18) 0.0073(16) 0.0127(16) 0.0180(17) C3 0.047(2) 0.0375(19) 0.044(2) 0.0099(17) 0.0174(17) 0.0264(17) C4 0.0307(17) 0.0357(18) 0.0414(19) 0.0143(16) 0.0101(14) 0.0184(14) C5 0.0225(14) 0.0267(16) 0.0276(15) 0.0108(13) 0.0061(12) 0.0099(12) C6 0.0228(14) 0.0302(16) 0.0276(15) 0.0144(13) 0.0092(12) 0.0123(12) C7 0.0258(15) 0.0312(16) 0.0285(16) 0.0135(13) 0.0101(13) 0.0145(13) C8 0.0282(16) 0.0358(17) 0.0233(15) 0.0095(13) 0.0050(12) 0.0155(13) C9 0.0187(14) 0.0301(16) 0.0285(16) 0.0128(13) 0.0042(12) 0.0081(12) C10 0.0282(16) 0.0365(18) 0.0222(15) 0.0087(13) 0.0039(13) 0.0191(14) C11 0.0367(17) 0.0310(17) 0.0249(16) 0.0055(13) 0.0081(13) 0.0186(14) C12 0.0375(17) 0.0291(16) 0.0310(16) 0.0083(13) 0.0115(14) 0.0218(14) C13 0.0255(15) 0.0260(15) 0.0255(15) 0.0086(13) 0.0130(12) 0.0098(12) C14 0.0372(17) 0.0345(17) 0.0219(15) 0.0090(13) 0.0104(13) 0.0196(14) C15 0.0306(16) 0.0310(16) 0.0291(16) 0.0099(14) 0.0109(13) 0.0176(13) N1 0.0286(13) 0.0282(13) 0.0253(13) 0.0071(11) 0.0115(11) 0.0149(11) N2 0.0265(13) 0.0376(15) 0.0250(13) 0.0158(12) 0.0060(10) 0.0197(11) O1 0.0226(11) 0.0297(11) 0.0269(11) 0.0047(9) 0.0011(9) 0.0127(9) O2 0.0317(13) 0.0614(17) 0.078(2) 0.0498(17) -0.0006(13) 0.0107(12) O3 0.0364(12) 0.0439(13) 0.0294(12) 0.0136(10) 0.0114(10) 0.0268(11) O4 0.0302(11) 0.0360(12) 0.0243(11) 0.0108(9) 0.0071(9) 0.0163(10) Zn1 0.0240(3) 0.0262(3) 0.0204(3) 0.0041(2) 0.00500(19) 0.0143(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(5) . ? C1 C6 1.391(4) . ? C1 H1 0.9300 . ? C2 C3 1.388(5) . ? C2 H2 0.9300 . ? C3 C4 1.363(5) . ? C3 H3 0.9300 . ? C4 C5 1.408(4) . ? C4 H4 0.9300 . ? C5 C6 1.404(4) . ? C5 C9 1.435(4) . ? C6 N2 1.393(4) . ? C7 O3 1.252(3) . ? C7 N2 1.351(4) . ? C7 C8 1.439(4) . ? C8 C9 1.347(4) . ? C8 H8 0.9300 . ? C9 C10 1.525(4) . ? C10 O2 1.238(4) . ? C10 O1 1.247(4) . ? C11 N1 1.329(4) . ? C11 C12 1.377(4) . ? C11 H11 0.9300 . ? C12 C13 1.387(4) . ? C12 H12 0.9300 . ? C13 C14 1.389(4) . ? C13 C13 1.469(6) 2_545 ? C14 C15 1.368(4) . ? C14 H14 0.9300 . ? C15 N1 1.337(4) . ? C15 H15 0.9300 . ? N1 Zn1 2.156(2) . ? N2 H2A 0.8600 . ? O1 Zn1 2.1141(19) . ? O4 Zn1 2.137(2) . ? O4 H4A 0.8582 . ? O4 H4B 0.8599 . ? Zn1 O1 2.1141(19) 2_556 ? Zn1 O4 2.137(2) 2_556 ? Zn1 N1 2.156(2) 2_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.4(3) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.3(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 117.2(3) . . ? C6 C5 C9 118.3(3) . . ? C4 C5 C9 124.5(3) . . ? C1 C6 N2 120.6(3) . . ? C1 C6 C5 121.4(3) . . ? N2 C6 C5 118.0(3) . . ? O3 C7 N2 119.9(3) . . ? O3 C7 C8 123.9(3) . . ? N2 C7 C8 116.3(3) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C5 120.9(3) . . ? C8 C9 C10 120.1(3) . . ? C5 C9 C10 119.0(3) . . ? O2 C10 O1 127.1(3) . . ? O2 C10 C9 116.8(3) . . ? O1 C10 C9 116.1(3) . . ? N1 C11 C12 123.6(3) . . ? N1 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C14 115.1(3) . . ? C12 C13 C13 122.2(3) . 2_545 ? C14 C13 C13 122.7(3) . 2_545 ? C15 C14 C13 120.9(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? N1 C15 C14 123.6(3) . . ? N1 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C11 N1 C15 116.1(3) . . ? C11 N1 Zn1 121.8(2) . . ? C15 N1 Zn1 121.96(19) . . ? C7 N2 C6 125.1(2) . . ? C7 N2 H2A 117.5 . . ? C6 N2 H2A 117.4 . . ? C10 O1 Zn1 129.18(19) . . ? Zn1 O4 H4A 104.8 . . ? Zn1 O4 H4B 122.3 . . ? H4A O4 H4B 101.4 . . ? O1 Zn1 O1 180.00(11) 2_556 . ? O1 Zn1 O4 88.93(8) 2_556 . ? O1 Zn1 O4 91.07(8) . . ? O1 Zn1 O4 91.07(8) 2_556 2_556 ? O1 Zn1 O4 88.93(8) . 2_556 ? O4 Zn1 O4 180.00(8) . 2_556 ? O1 Zn1 N1 90.05(8) 2_556 . ? O1 Zn1 N1 89.95(8) . . ? O4 Zn1 N1 93.64(9) . . ? O4 Zn1 N1 86.36(9) 2_556 . ? O1 Zn1 N1 89.95(8) 2_556 2_556 ? O1 Zn1 N1 90.05(8) . 2_556 ? O4 Zn1 N1 86.36(9) . 2_556 ? O4 Zn1 N1 93.64(9) 2_556 2_556 ? N1 Zn1 N1 180.00(12) . 2_556 ? 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 C6 C1 C2 C3 -0.5(5) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C3 C4 C5 C6 -1.3(5) . . . . ? C3 C4 C5 C9 179.0(3) . . . . ? C2 C1 C6 N2 178.1(3) . . . . ? C2 C1 C6 C5 -0.6(5) . . . . ? C4 C5 C6 C1 1.5(4) . . . . ? C9 C5 C6 C1 -178.7(3) . . . . ? C4 C5 C6 N2 -177.2(3) . . . . ? C9 C5 C6 N2 2.6(4) . . . . ? O3 C7 C8 C9 -174.7(3) . . . . ? N2 C7 C8 C9 3.9(4) . . . . ? C7 C8 C9 C5 -2.5(4) . . . . ? C7 C8 C9 C10 175.9(3) . . . . ? C6 C5 C9 C8 -0.8(4) . . . . ? C4 C5 C9 C8 179.0(3) . . . . ? C6 C5 C9 C10 -179.2(3) . . . . ? C4 C5 C9 C10 0.5(4) . . . . ? C8 C9 C10 O2 -102.9(4) . . . . ? C5 C9 C10 O2 75.5(4) . . . . ? C8 C9 C10 O1 78.3(4) . . . . ? C5 C9 C10 O1 -103.2(3) . . . . ? N1 C11 C12 C13 -0.9(5) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C11 C12 C13 C13 -179.0(3) . . . 2_545 ? C12 C13 C14 C15 -0.4(4) . . . . ? C13 C13 C14 C15 179.9(3) 2_545 . . . ? C13 C14 C15 N1 -0.9(5) . . . . ? C12 C11 N1 C15 -0.3(5) . . . . ? C12 C11 N1 Zn1 176.0(2) . . . . ? C14 C15 N1 C11 1.2(4) . . . . ? C14 C15 N1 Zn1 -175.1(2) . . . . ? O3 C7 N2 C6 176.6(3) . . . . ? C8 C7 N2 C6 -2.0(4) . . . . ? C1 C6 N2 C7 -179.8(3) . . . . ? C5 C6 N2 C7 -1.1(4) . . . . ? O2 C10 O1 Zn1 0.1(5) . . . . ? C9 C10 O1 Zn1 178.69(18) . . . . ? C10 O1 Zn1 O1 -122(100) . . . 2_556 ? C10 O1 Zn1 O4 6.9(2) . . . . ? C10 O1 Zn1 O4 -173.1(2) . . . 2_556 ? C10 O1 Zn1 N1 100.6(2) . . . . ? C10 O1 Zn1 N1 -79.4(2) . . . 2_556 ? C11 N1 Zn1 O1 -158.8(2) . . . 2_556 ? C15 N1 Zn1 O1 17.2(2) . . . 2_556 ? C11 N1 Zn1 O1 21.2(2) . . . . ? C15 N1 Zn1 O1 -162.8(2) . . . . ? C11 N1 Zn1 O4 112.2(2) . . . . ? C15 N1 Zn1 O4 -71.8(2) . . . . ? C11 N1 Zn1 O4 -67.8(2) . . . 2_556 ? C15 N1 Zn1 O4 108.2(2) . . . 2_556 ? C11 N1 Zn1 N1 -58(100) . . . 2_556 ? C15 N1 Zn1 N1 118(100) . . . 2_556 ? 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 O4 H4B O3 0.86 1.87 2.719(3) 170.6 2_656 N2 H2A O3 0.86 2.13 2.884(3) 146.6 2_757 O4 H4A O2 0.86 1.85 2.662(3) 156.3 . _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.395 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.073 # Attachment '- 10.cif' data_10 _database_code_depnum_ccdc_archive 'CCDC 853357' #TrackingRef '- 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 Co N6 O16' _chemical_formula_weight 799.61 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 6.8644(10) _cell_length_b 10.5393(16) _cell_length_c 13.217(2) _cell_angle_alpha 100.562(2) _cell_angle_beta 104.377(2) _cell_angle_gamma 105.700(2) _cell_volume 858.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3498 _cell_measurement_theta_min 2.487 _cell_measurement_theta_max 23.105 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 417 _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7588 _exptl_absorpt_correction_T_max 0.9072 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4540 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.59 _reflns_number_total 3173 _reflns_number_gt 2997 _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^)+(0.0450P)^2^+0.3615P] 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 3173 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0847 _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 C1 C 0.4773(3) 0.98860(17) 0.15157(14) 0.0228(4) Uani 1 1 d . . . C2 C 0.4492(3) 0.97094(17) 0.25391(14) 0.0223(4) Uani 1 1 d . . . H2 H 0.5701 1.0041 0.3173 0.027 Uiso 1 1 calc R . . C3 C 0.2553(3) 0.90839(17) 0.26152(14) 0.0208(4) Uani 1 1 d . . . C4 C 0.2339(3) 0.89928(17) 0.37215(14) 0.0210(4) Uani 1 1 d . . . C5 C 0.0696(3) 0.85249(17) 0.16577(14) 0.0215(4) Uani 1 1 d . . . C6 C 0.0998(3) 0.86641(17) 0.06640(15) 0.0222(4) Uani 1 1 d . . . C7 C -0.0713(3) 0.81435(19) -0.03020(15) 0.0282(4) Uani 1 1 d . . . H7 H -0.0497 0.8257 -0.0967 0.034 Uiso 1 1 calc R . . C8 C -0.2704(3) 0.7468(2) -0.02775(17) 0.0355(5) Uani 1 1 d . . . H8 H -0.3872 0.7112 -0.0930 0.043 Uiso 1 1 calc R . . C9 C -0.3037(3) 0.7295(2) 0.06985(17) 0.0359(5) Uani 1 1 d . . . H9 H -0.4420 0.6814 0.0703 0.043 Uiso 1 1 calc R . . C10 C -0.1364(3) 0.78209(19) 0.16505(16) 0.0285(4) Uani 1 1 d . . . H10 H -0.1604 0.7707 0.2311 0.034 Uiso 1 1 calc R . . C11 C 0.2107(3) 0.54600(17) 0.32797(14) 0.0205(4) Uani 1 1 d . . . H11 H 0.3341 0.5821 0.3901 0.025 Uiso 1 1 calc R . . C12 C 0.2340(3) 0.55775(18) 0.22890(14) 0.0229(4) Uani 1 1 d . . . H12 H 0.3699 0.6013 0.2232 0.028 Uiso 1 1 calc R . . C13 C 0.0560(3) 0.50500(18) 0.13889(14) 0.0242(4) Uani 1 1 d . . . C14 C -0.1378(3) 0.4377(2) 0.14992(16) 0.0397(5) Uani 1 1 d . . . H14 H -0.2620 0.3966 0.0884 0.048 Uiso 1 1 calc R . . C15 C -0.1469(3) 0.4315(2) 0.25154(16) 0.0347(5) Uani 1 1 d . . . H15 H -0.2803 0.3862 0.2590 0.042 Uiso 1 1 calc R . . Co1 Co 0.0000 0.5000 0.5000 0.01604(11) Uani 1 2 d S . . N1 N 0.3010(2) 0.93328(15) 0.06371(12) 0.0234(3) Uani 1 1 d . . . N2 N 0.0242(2) 0.48675(14) 0.34086(11) 0.0203(3) Uani 1 1 d . . . N3 N 0.0846(2) 0.52524(16) 0.03890(12) 0.0268(3) Uani 1 1 d . . . O1 O 0.3476(2) 0.84377(13) 0.42502(10) 0.0265(3) Uani 1 1 d . . . O2 O 0.1026(2) 0.94671(13) 0.40192(10) 0.0274(3) Uani 1 1 d . . . O3 O 0.6522(2) 1.05162(14) 0.14196(10) 0.0287(3) Uani 1 1 d . . . O4 O 0.17406(19) 0.71243(12) 0.55302(10) 0.0218(3) Uani 1 1 d . . . O5 O 0.28558(19) 0.46087(12) 0.54382(10) 0.0245(3) Uani 1 1 d . . . O6 O 0.2971(2) 0.22779(13) 0.59647(12) 0.0309(3) Uani 1 1 d . . . O7 O 0.5898(2) 0.70076(14) 0.67785(12) 0.0327(3) Uani 1 1 d . . . O8 O -0.00309(19) 0.85062(12) 0.67639(10) 0.0257(3) Uani 1 1 d . . . H1A H 0.3115 0.9386 -0.0013 0.031 Uiso 1 1 d R . . H6A H 0.3860 0.1909 0.5833 0.039 Uiso 1 1 d R . . H8A H -0.0222 0.9184 0.6545 0.039 Uiso 1 1 d R . . H5A H 0.3948 0.5218 0.5894 0.039 Uiso 1 1 d R . . H5B H 0.2870 0.3868 0.5590 0.039 Uiso 1 1 d R . . H8B H 0.0970 0.8865 0.7366 0.039 Uiso 1 1 d R . . H7A H 0.5126 0.7440 0.6530 0.039 Uiso 1 1 d R . . H6B H 0.1794 0.1641 0.5743 0.039 Uiso 1 1 d R . . H7B H 0.7152 0.7412 0.6802 0.039 Uiso 1 1 d R . . H4A H 0.1164 0.7584 0.5884 0.039 Uiso 1 1 d R . . H4B H 0.2136 0.7595 0.5117 0.039 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0237(9) 0.0241(8) 0.0234(9) 0.0096(7) 0.0100(7) 0.0079(7) C2 0.0217(9) 0.0249(8) 0.0215(9) 0.0091(7) 0.0079(7) 0.0067(7) C3 0.0252(9) 0.0180(8) 0.0242(9) 0.0088(7) 0.0118(7) 0.0091(7) C4 0.0203(9) 0.0185(8) 0.0238(9) 0.0068(7) 0.0097(7) 0.0022(7) C5 0.0226(9) 0.0210(8) 0.0246(9) 0.0087(7) 0.0108(7) 0.0081(7) C6 0.0219(9) 0.0225(8) 0.0254(9) 0.0094(7) 0.0103(7) 0.0080(7) C7 0.0278(10) 0.0344(10) 0.0229(9) 0.0099(8) 0.0088(8) 0.0086(8) C8 0.0226(10) 0.0462(12) 0.0296(11) 0.0075(9) 0.0042(8) 0.0044(9) C9 0.0207(10) 0.0454(12) 0.0364(11) 0.0098(9) 0.0108(9) 0.0019(9) C10 0.0253(10) 0.0317(10) 0.0291(10) 0.0099(8) 0.0125(8) 0.0059(8) C11 0.0188(8) 0.0249(8) 0.0194(9) 0.0078(7) 0.0066(7) 0.0080(7) C12 0.0200(9) 0.0291(9) 0.0224(9) 0.0097(7) 0.0105(7) 0.0072(7) C13 0.0266(10) 0.0295(9) 0.0181(9) 0.0088(7) 0.0111(7) 0.0065(8) C14 0.0229(10) 0.0633(14) 0.0179(10) 0.0120(9) 0.0025(8) -0.0066(10) C15 0.0212(10) 0.0523(12) 0.0217(10) 0.0123(9) 0.0076(8) -0.0041(9) Co1 0.01618(18) 0.02025(17) 0.01411(17) 0.00759(12) 0.00682(12) 0.00600(13) N1 0.0221(8) 0.0304(8) 0.0205(8) 0.0119(6) 0.0102(6) 0.0067(6) N2 0.0208(7) 0.0235(7) 0.0179(7) 0.0076(6) 0.0082(6) 0.0058(6) N3 0.0263(8) 0.0354(9) 0.0178(7) 0.0095(6) 0.0092(6) 0.0049(7) O1 0.0293(7) 0.0317(7) 0.0279(7) 0.0167(6) 0.0154(6) 0.0136(6) O2 0.0287(7) 0.0338(7) 0.0288(7) 0.0125(6) 0.0169(6) 0.0149(6) O3 0.0208(7) 0.0399(7) 0.0243(7) 0.0133(6) 0.0099(5) 0.0026(6) O4 0.0262(7) 0.0211(6) 0.0226(6) 0.0093(5) 0.0134(5) 0.0075(5) O5 0.0191(6) 0.0251(6) 0.0298(7) 0.0104(5) 0.0059(5) 0.0078(5) O6 0.0234(7) 0.0277(7) 0.0452(8) 0.0131(6) 0.0141(6) 0.0089(6) O7 0.0218(7) 0.0314(7) 0.0453(8) 0.0135(6) 0.0108(6) 0.0072(6) O8 0.0230(6) 0.0267(6) 0.0274(7) 0.0075(5) 0.0078(5) 0.0080(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O3 1.254(2) . ? C1 N1 1.351(2) . ? C1 C2 1.450(2) . ? C2 C3 1.354(2) . ? C2 H2 0.9500 . ? C3 C5 1.447(3) . ? C3 C4 1.523(2) . ? C4 O2 1.251(2) . ? C4 O1 1.251(2) . ? C5 C10 1.404(3) . ? C5 C6 1.407(2) . ? C6 N1 1.383(2) . ? C6 C7 1.400(3) . ? C7 C8 1.371(3) . ? C7 H7 0.9500 . ? C8 C9 1.400(3) . ? C8 H8 0.9500 . ? C9 C10 1.375(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 N2 1.331(2) . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.373(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 N3 1.428(2) . ? C14 C15 1.372(3) . ? C14 H14 0.9500 . ? C15 N2 1.342(2) . ? C15 H15 0.9500 . ? Co1 O5 2.0760(12) . ? Co1 O5 2.0760(12) 2_566 ? Co1 O4 2.1195(12) . ? Co1 O4 2.1195(12) 2_566 ? Co1 N2 2.1331(14) . ? Co1 N2 2.1331(14) 2_566 ? N1 H1A 0.8899 . ? N3 N3 1.249(3) 2_565 ? O4 H4A 0.8496 . ? O4 H4B 0.8469 . ? O5 H5A 0.8434 . ? O5 H5B 0.8429 . ? O6 H6A 0.8427 . ? O6 H6B 0.8404 . ? O7 H7A 0.8339 . ? O7 H7B 0.8404 . ? O8 H8A 0.8479 . ? O8 H8B 0.8524 . ? 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 C1 N1 120.09(16) . . ? O3 C1 C2 123.72(16) . . ? N1 C1 C2 116.19(15) . . ? C3 C2 C1 121.72(17) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C5 120.37(16) . . ? C2 C3 C4 119.34(16) . . ? C5 C3 C4 120.29(15) . . ? O2 C4 O1 125.58(16) . . ? O2 C4 C3 117.19(15) . . ? O1 C4 C3 117.23(15) . . ? C10 C5 C6 118.11(17) . . ? C10 C5 C3 124.46(16) . . ? C6 C5 C3 117.41(16) . . ? N1 C6 C7 119.23(16) . . ? N1 C6 C5 119.74(16) . . ? C7 C6 C5 121.03(16) . . ? C8 C7 C6 119.25(18) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.74(18) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.11(18) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 120.75(18) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? N2 C11 C12 123.40(16) . . ? N2 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C13 C12 C11 118.38(16) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 119.05(16) . . ? C12 C13 N3 116.75(16) . . ? C14 C13 N3 124.20(17) . . ? C15 C14 C13 118.65(18) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N2 C15 C14 122.99(17) . . ? N2 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? O5 Co1 O5 180.000(1) . 2_566 ? O5 Co1 O4 89.05(5) . . ? O5 Co1 O4 90.95(5) 2_566 . ? O5 Co1 O4 90.95(5) . 2_566 ? O5 Co1 O4 89.05(5) 2_566 2_566 ? O4 Co1 O4 180.00(7) . 2_566 ? O5 Co1 N2 88.53(5) . . ? O5 Co1 N2 91.47(5) 2_566 . ? O4 Co1 N2 92.12(5) . . ? O4 Co1 N2 87.88(5) 2_566 . ? O5 Co1 N2 91.47(5) . 2_566 ? O5 Co1 N2 88.53(5) 2_566 2_566 ? O4 Co1 N2 87.88(5) . 2_566 ? O4 Co1 N2 92.12(5) 2_566 2_566 ? N2 Co1 N2 180.0 . 2_566 ? C1 N1 C6 124.51(15) . . ? C1 N1 H1A 119.4 . . ? C6 N1 H1A 116.1 . . ? C11 N2 C15 117.43(15) . . ? C11 N2 Co1 119.92(11) . . ? C15 N2 Co1 122.35(12) . . ? N3 N3 C13 112.86(19) 2_565 . ? Co1 O4 H4A 112.8 . . ? Co1 O4 H4B 124.0 . . ? H4A O4 H4B 104.8 . . ? Co1 O5 H5A 119.9 . . ? Co1 O5 H5B 119.9 . . ? H5A O5 H5B 105.8 . . ? H6A O6 H6B 105.4 . . ? H7A O7 H7B 108.3 . . ? H8A O8 H8B 104.3 . . ? 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 C1 C2 C3 176.45(16) . . . . ? N1 C1 C2 C3 -3.1(3) . . . . ? C1 C2 C3 C5 2.2(3) . . . . ? C1 C2 C3 C4 -176.90(15) . . . . ? C2 C3 C4 O2 124.36(18) . . . . ? C5 C3 C4 O2 -54.8(2) . . . . ? C2 C3 C4 O1 -56.3(2) . . . . ? C5 C3 C4 O1 124.53(17) . . . . ? C2 C3 C5 C10 177.82(17) . . . . ? C4 C3 C5 C10 -3.1(3) . . . . ? C2 C3 C5 C6 -0.2(2) . . . . ? C4 C3 C5 C6 178.93(15) . . . . ? C10 C5 C6 N1 -179.02(16) . . . . ? C3 C5 C6 N1 -0.9(2) . . . . ? C10 C5 C6 C7 1.4(3) . . . . ? C3 C5 C6 C7 179.57(16) . . . . ? N1 C6 C7 C8 179.30(18) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C8 C9 C10 C5 -0.5(3) . . . . ? C6 C5 C10 C9 -0.6(3) . . . . ? C3 C5 C10 C9 -178.57(18) . . . . ? N2 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 -2.5(3) . . . . ? C11 C12 C13 N3 176.90(16) . . . . ? C12 C13 C14 C15 3.0(3) . . . . ? N3 C13 C14 C15 -176.4(2) . . . . ? C13 C14 C15 N2 -0.7(4) . . . . ? O3 C1 N1 C6 -177.52(16) . . . . ? C2 C1 N1 C6 2.1(3) . . . . ? C7 C6 N1 C1 179.41(17) . . . . ? C5 C6 N1 C1 -0.1(3) . . . . ? C12 C11 N2 C15 2.6(3) . . . . ? C12 C11 N2 Co1 -171.16(13) . . . . ? C14 C15 N2 C11 -2.1(3) . . . . ? C14 C15 N2 Co1 171.53(18) . . . . ? O5 Co1 N2 C11 -43.08(13) . . . . ? O5 Co1 N2 C11 136.92(13) 2_566 . . . ? O4 Co1 N2 C11 45.91(13) . . . . ? O4 Co1 N2 C11 -134.09(13) 2_566 . . . ? N2 Co1 N2 C11 -50(100) 2_566 . . . ? O5 Co1 N2 C15 143.47(16) . . . . ? O5 Co1 N2 C15 -36.53(16) 2_566 . . . ? O4 Co1 N2 C15 -127.54(15) . . . . ? O4 Co1 N2 C15 52.46(15) 2_566 . . . ? N2 Co1 N2 C15 137(100) 2_566 . . . ? C12 C13 N3 N3 -179.8(2) . . . 2_565 ? C14 C13 N3 N3 -0.4(3) . . . 2_565 ? 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 O4 H4B O1 0.85 1.84 2.6766(16) 166.9 . O4 H4A O8 0.85 1.86 2.7076(17) 174.4 . O7 H7A O4 0.83 2.27 2.9680(19) 141.4 . O5 H5B O6 0.84 1.85 2.6889(18) 178.1 . O5 H5A O7 0.84 1.94 2.7487(19) 160.3 . O7 H7B O8 0.84 1.98 2.8200(18) 173.2 1_655 O6 H6B O2 0.84 2.10 2.8677(18) 151.2 2_566 O8 H8B O3 0.85 1.90 2.7398(19) 169.3 2_676 O8 H8A O2 0.85 1.87 2.7110(18) 172.3 2_576 O6 H6A O1 0.84 1.98 2.8032(18) 163.8 2_666 N1 H1A O3 0.89 1.95 2.843(2) 177.2 2_675 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.59 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.322 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.060 # Attachment '- 11.cif' data_11 _database_code_depnum_ccdc_archive 'CCDC 853358' #TrackingRef '- 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Mn N6 O15' _chemical_formula_weight 777.60 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.913(2) _cell_length_b 19.061(4) _cell_length_c 17.668(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3338.4(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4372 _cell_measurement_theta_min 2.305 _cell_measurement_theta_max 27.138 _exptl_crystal_description bar _exptl_crystal_colour red _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1620 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7788 _exptl_absorpt_correction_T_max 0.9719 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 13136 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2947 _reflns_number_gt 2448 _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^)+(0.0423P)^2^+1.6975P] 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 2947 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1809(2) 0.21165(10) 0.21637(11) 0.0188(4) Uani 1 1 d . . . C2 C 0.0516(2) 0.25685(10) 0.21492(11) 0.0171(4) Uani 1 1 d . . . C3 C 0.0718(2) 0.33559(10) 0.23208(11) 0.0180(4) Uani 1 1 d . . . H3 H 0.1416 0.3417 0.2724 0.022 Uiso 1 1 calc R . . C4 C 0.0952(2) 0.38697(11) 0.16988(12) 0.0214(5) Uani 1 1 d . . . C5 C -0.0047(2) 0.30156(11) 0.08424(12) 0.0217(5) Uani 1 1 d . . . C6 C -0.0166(2) 0.24851(10) 0.13832(12) 0.0194(4) Uani 1 1 d . . . C7 C -0.0867(2) 0.18808(11) 0.11831(12) 0.0237(5) Uani 1 1 d . . . H7 H -0.0936 0.1507 0.1536 0.028 Uiso 1 1 calc R . . C8 C -0.1464(2) 0.18145(13) 0.04791(13) 0.0303(5) Uani 1 1 d . . . H8 H -0.1961 0.1403 0.0358 0.036 Uiso 1 1 calc R . . C9 C -0.1339(2) 0.23448(13) -0.00471(13) 0.0314(6) Uani 1 1 d . . . H9 H -0.1748 0.2299 -0.0531 0.038 Uiso 1 1 calc R . . C10 C -0.0619(2) 0.29412(12) 0.01292(12) 0.0295(5) Uani 1 1 d . . . H10 H -0.0514 0.3302 -0.0237 0.035 Uiso 1 1 calc R . . C11 C 0.4384(2) 0.37343(11) 0.16486(11) 0.0223(5) Uani 1 1 d . . . H11 H 0.3702 0.3729 0.2026 0.027 Uiso 1 1 calc R . . C12 C 0.4400(2) 0.42804(11) 0.11466(12) 0.0248(5) Uani 1 1 d . . . H12 H 0.3747 0.4644 0.1174 0.030 Uiso 1 1 calc R . . C13 C 0.5390(2) 0.42873(11) 0.06000(12) 0.0237(5) Uani 1 1 d . . . C14 C 0.6342(2) 0.37562(12) 0.05819(12) 0.0274(5) Uani 1 1 d . . . H14 H 0.7044 0.3757 0.0216 0.033 Uiso 1 1 calc R . . C15 C 0.62419(6) 0.322335(18) 0.11113(3) 0.0234(5) Uani 1 1 d . . . H15 H 0.6887 0.2855 0.1099 0.028 Uiso 1 1 calc R . . H1A H 0.0750 0.3930 0.0655 0.028 Uiso 1 1 d R . . Mn1 Mn 0.50000(6) 0.232211(18) 0.25000(3) 0.01706(14) Uani 1 2 d SR . . N1 N 0.06279(6) 0.365370(18) 0.10050(3) 0.0245(4) Uani 1 1 d R . . N2 N 0.52767(6) 0.320550(18) 0.16387(3) 0.0207(4) Uani 1 1 d R . . N3 N 0.55197(6) 0.482461(18) 0.00405(3) 0.0304(5) Uani 1 1 d R . . O1 O 0.28891(6) 0.244638(18) 0.22383(3) 0.0284(4) Uani 1 1 d R . . O2 O 0.16953(6) 0.147348(18) 0.20727(3) 0.0353(4) Uani 1 1 d R . . O3 O 0.14030(6) 0.446314(18) 0.18342(3) 0.0282(4) Uani 1 1 d R . . O4 O 0.55799(6) 0.151958(18) 0.16870(3) 0.0333(4) Uani 1 1 d R . . H4A H 0.6139 0.1192 0.1785 0.040 Uiso 1 1 d R . . H4B H 0.4890 0.1301 0.1543 0.040 Uiso 1 1 d R . . O5 O 0.34357(19) 0.07799(9) 0.11443(9) 0.0406(5) Uani 1 1 d . . . H5A H 0.2857 0.0987 0.1428 0.049 Uiso 1 1 d R . . H5B H 0.3483 0.0371 0.1338 0.049 Uiso 1 1 d R . . O6 O 0.6308(2) 0.02830(10) 0.01731(10) 0.0483(5) Uani 1 1 d . . . O7 O 0.7181(2) 0.02214(11) 0.17704(11) 0.0600(6) Uani 1 1 d . . . H7A H 0.6744 -0.0032 0.2083 0.072 Uiso 1 1 d R . . H7B H 0.7994 0.0269 0.1922 0.072 Uiso 1 1 d R . . O8 O 0.0000 0.03972(15) 0.2500 0.0895(13) Uani 1 2 d S . . H8A H 0.0506 0.0656 0.2232 0.107 Uiso 1 1 d R . . H6A H 0.6510 0.0271 0.0635 0.107 Uiso 1 1 d R . . H6B H 0.5517 0.0135 0.0064 0.107 Uiso 0.50 1 d PR A 1 H6B' H 0.6605 -0.0052 -0.0101 0.107 Uiso 0.50 1 d PR B 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 C1 0.0163(11) 0.0200(11) 0.0202(10) 0.0017(8) 0.0016(9) 0.0017(9) C2 0.0130(10) 0.0159(10) 0.0224(10) 0.0012(8) 0.0007(9) -0.0005(8) C3 0.0153(11) 0.0158(10) 0.0229(11) 0.0001(8) -0.0005(8) 0.0001(8) C4 0.0144(10) 0.0188(11) 0.0309(12) -0.0003(9) 0.0042(9) 0.0027(9) C5 0.0177(11) 0.0223(11) 0.0252(11) -0.0012(9) 0.0034(9) 0.0028(9) C6 0.0142(11) 0.0202(11) 0.0238(11) -0.0026(8) 0.0028(8) 0.0042(8) C7 0.0203(12) 0.0205(11) 0.0304(12) -0.0044(9) 0.0015(9) 0.0008(9) C8 0.0246(13) 0.0329(13) 0.0335(13) -0.0147(10) 0.0002(10) -0.0009(10) C9 0.0286(13) 0.0436(15) 0.0220(11) -0.0110(10) -0.0004(10) 0.0059(11) C10 0.0298(13) 0.0374(14) 0.0212(11) 0.0009(10) 0.0039(10) 0.0071(11) C11 0.0194(11) 0.0264(11) 0.0209(10) 0.0019(9) 0.0025(9) 0.0023(9) C12 0.0235(12) 0.0229(11) 0.0279(11) 0.0021(9) 0.0006(10) 0.0061(10) C13 0.0224(12) 0.0226(11) 0.0261(11) 0.0046(9) 0.0007(9) -0.0001(9) C14 0.0236(12) 0.0296(12) 0.0290(12) 0.0047(10) 0.0080(10) 0.0037(10) C15 0.0191(11) 0.0239(11) 0.0273(11) 0.0009(9) -0.0003(9) 0.0041(9) Mn1 0.0129(2) 0.0178(2) 0.0204(2) 0.000 -0.00059(18) 0.000 N1 0.0283(11) 0.0206(9) 0.0245(9) 0.0068(7) 0.0028(8) -0.0006(8) N2 0.0177(10) 0.0232(9) 0.0210(9) 0.0003(7) -0.0010(7) 0.0009(7) N3 0.0301(11) 0.0286(11) 0.0325(10) 0.0105(9) 0.0061(9) 0.0056(8) O1 0.0127(8) 0.0280(8) 0.0447(9) -0.0005(7) -0.0038(7) -0.0006(7) O2 0.0248(9) 0.0172(8) 0.0639(12) -0.0031(7) 0.0057(8) 0.0032(7) O3 0.0308(9) 0.0165(8) 0.0374(9) 0.0023(6) 0.0045(7) -0.0037(7) O4 0.0366(10) 0.0285(9) 0.0349(9) -0.0048(7) 0.0017(8) 0.0058(8) O5 0.0531(12) 0.0251(9) 0.0435(10) 0.0029(7) 0.0138(9) 0.0046(8) O6 0.0603(14) 0.0482(11) 0.0364(10) 0.0032(8) -0.0009(9) 0.0010(10) O7 0.0598(14) 0.0659(14) 0.0542(12) 0.0077(10) 0.0000(10) -0.0091(12) O8 0.129(4) 0.0372(18) 0.102(3) 0.000 0.063(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.241(2) . ? C1 O1 1.249(2) . ? C1 C2 1.545(3) . ? C2 C6 1.521(3) . ? C2 C3 1.544(3) . ? C2 C2 1.607(4) 3 ? C3 C4 1.490(3) . ? C3 C3 1.559(4) 3 ? C3 H3 1.0000 . ? C4 O3 1.240(2) . ? C4 N1 1.332(2) . ? C5 C10 1.389(3) . ? C5 C6 1.396(3) . ? C5 N1 1.418(2) . ? C6 C7 1.391(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.379(4) . ? C8 H8 0.9500 . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 N2 1.341(2) . ? C11 C12 1.368(3) . ? C11 H11 0.9500 . ? C12 C13 1.377(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 N3 1.429(2) . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 N2 1.3359 . ? C15 H15 0.9500 . ? Mn1 O1 2.1561 . ? Mn1 O1 2.1561(13) 3_655 ? Mn1 O4 2.1757 . ? Mn1 O4 2.1757 3_655 ? Mn1 N2 2.2861 3_655 ? Mn1 N2 2.2861 . ? N1 H1A 0.8212 . ? N3 N3 1.2366(11) 5_665 ? O4 H4A 0.8530 . ? O4 H4B 0.8400 . ? O5 H5A 0.8586 . ? O5 H5B 0.8521 . ? O6 H6A 0.8404 . ? O6 H6B 0.8555 . ? O6 H6B' 0.8531 . ? O7 H7A 0.8522 . ? O7 H7B 0.8537 . ? O8 H8A 0.8485 . ? 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 C1 O1 126.07(17) . . ? O2 C1 C2 118.23(17) . . ? O1 C1 C2 115.63(16) . . ? C6 C2 C3 109.51(16) . . ? C6 C2 C1 108.98(16) . . ? C3 C2 C1 115.51(17) . . ? C6 C2 C2 113.8(2) . 3 ? C3 C2 C2 86.07(11) . 3 ? C1 C2 C2 121.02(17) . 3 ? C4 C3 C2 120.94(17) . . ? C4 C3 C3 116.21(17) . 3 ? C2 C3 C3 87.76(11) . 3 ? C4 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C3 C3 H3 110.0 3 . ? O3 C4 N1 123.14(17) . . ? O3 C4 C3 120.89(18) . . ? N1 C4 C3 115.97(16) . . ? C10 C5 C6 120.8(2) . . ? C10 C5 N1 117.65(18) . . ? C6 C5 N1 121.50(18) . . ? C7 C6 C5 117.9(2) . . ? C7 C6 C2 122.32(18) . . ? C5 C6 C2 119.72(18) . . ? C8 C7 C6 121.2(2) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 120.0(2) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? N2 C11 C12 123.78(19) . . ? N2 C11 H11 118.1 . . ? C12 C11 H11 118.1 . . ? C11 C12 C13 118.0(2) . . ? C11 C12 H12 121.0 . . ? C13 C12 H12 121.0 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 N3 123.77(18) . . ? C14 C13 N3 116.55(18) . . ? C13 C14 C15 118.19(18) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? N2 C15 C14 122.76(9) . . ? N2 C15 H15 118.6 . . ? C14 C15 H15 118.6 . . ? O1 Mn1 O1 167.4 . 3_655 ? O1 Mn1 O4 101.1 . . ? O1 Mn1 O4 87.8 3_655 . ? O1 Mn1 O4 87.8 . 3_655 ? O1 Mn1 O4 101.1 3_655 3_655 ? O4 Mn1 O4 90.7 . 3_655 ? O1 Mn1 N2 86.9 . 3_655 ? O1 Mn1 N2 83.8 3_655 3_655 ? O4 Mn1 N2 171.5 . 3_655 ? O4 Mn1 N2 92.7 3_655 3_655 ? O1 Mn1 N2 83.8 . . ? O1 Mn1 N2 86.9 3_655 . ? O4 Mn1 N2 92.7 . . ? O4 Mn1 N2 171.5 3_655 . ? N2 Mn1 N2 85.1 3_655 . ? C4 N1 C5 124.43(13) . . ? C4 N1 H1A 117.2 . . ? C5 N1 H1A 117.9 . . ? C15 N2 C11 117.54(9) . . ? C15 N2 Mn1 124.7 . . ? C11 N2 Mn1 117.76(9) . . ? N3 N3 C13 113.13(11) 5_665 . ? C1 O1 Mn1 143.09(9) . . ? Mn1 O4 H4A 123.6 . . ? Mn1 O4 H4B 109.5 . . ? H4A O4 H4B 103.1 . . ? H5A O5 H5B 102.9 . . ? H6A O6 H6B 115.3 . . ? H6A O6 H6B' 116.6 . . ? H6B O6 H6B' 86.7 . . ? H7A O7 H7B 109.6 . . ? 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 C1 C2 C6 -60.3(2) . . . . ? O1 C1 C2 C6 116.98(18) . . . . ? O2 C1 C2 C3 175.95(16) . . . . ? O1 C1 C2 C3 -6.8(2) . . . . ? O2 C1 C2 C2 74.5(2) . . . 3 ? O1 C1 C2 C2 -108.20(19) . . . 3 ? C6 C2 C3 C4 -31.4(3) . . . . ? C1 C2 C3 C4 92.1(2) . . . . ? C2 C2 C3 C4 -145.3(2) 3 . . . ? C6 C2 C3 C3 88.1(2) . . . 3 ? C1 C2 C3 C3 -148.45(18) . . . 3 ? C2 C2 C3 C3 -25.80(19) 3 . . 3 ? C2 C3 C4 O3 -164.05(17) . . . . ? C3 C3 C4 O3 91.8(2) 3 . . . ? C2 C3 C4 N1 17.0(3) . . . . ? C3 C3 C4 N1 -87.1(2) 3 . . . ? C10 C5 C6 C7 0.3(3) . . . . ? N1 C5 C6 C7 178.76(17) . . . . ? C10 C5 C6 C2 177.66(19) . . . . ? N1 C5 C6 C2 -3.9(3) . . . . ? C3 C2 C6 C7 -158.51(19) . . . . ? C1 C2 C6 C7 74.3(2) . . . . ? C2 C2 C6 C7 -64.1(2) 3 . . . ? C3 C2 C6 C5 24.3(3) . . . . ? C1 C2 C6 C5 -103.0(2) . . . . ? C2 C2 C6 C5 118.68(16) 3 . . . ? C5 C6 C7 C8 -2.0(3) . . . . ? C2 C6 C7 C8 -179.2(2) . . . . ? C6 C7 C8 C9 1.9(3) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 C5 -1.5(3) . . . . ? C6 C5 C10 C9 1.4(3) . . . . ? N1 C5 C10 C9 -177.09(18) . . . . ? N2 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 -1.1(3) . . . . ? C11 C12 C13 N3 179.83(18) . . . . ? C12 C13 C14 C15 1.4(3) . . . . ? N3 C13 C14 C15 -179.48(16) . . . . ? C13 C14 C15 N2 -0.6(2) . . . . ? O3 C4 N1 C5 -171.55(15) . . . . ? C3 C4 N1 C5 7.4(2) . . . . ? C10 C5 N1 C4 163.97(18) . . . . ? C6 C5 N1 C4 -14.5(3) . . . . ? C14 C15 N2 C11 -0.54(15) . . . . ? C14 C15 N2 Mn1 177.47(12) . . . . ? C12 C11 N2 C15 0.9(2) . . . . ? C12 C11 N2 Mn1 -177.29(16) . . . . ? O1 Mn1 N2 C15 -137.6 . . . . ? O1 Mn1 N2 C15 51.0 3_655 . . . ? O4 Mn1 N2 C15 -36.7 . . . . ? O4 Mn1 N2 C15 -149.67(16) 3_655 . . . ? N2 Mn1 N2 C15 135.0 3_655 . . . ? O1 Mn1 N2 C11 40.41(10) . . . . ? O1 Mn1 N2 C11 -131.04(11) 3_655 . . . ? O4 Mn1 N2 C11 141.27(10) . . . . ? O4 Mn1 N2 C11 28.33(17) 3_655 . . . ? N2 Mn1 N2 C11 -46.96(10) 3_655 . . . ? C12 C13 N3 N3 -18.3(2) . . . 5_665 ? C14 C13 N3 N3 162.62(16) . . . 5_665 ? O2 C1 O1 Mn1 -17.4(3) . . . . ? C2 C1 O1 Mn1 165.56(9) . . . . ? O1 Mn1 O1 C1 -172.2(2) 3_655 . . . ? O4 Mn1 O1 C1 53.49(16) . . . . ? O4 Mn1 O1 C1 -36.75(15) 3_655 . . . ? N2 Mn1 O1 C1 -129.55(17) 3_655 . . . ? N2 Mn1 O1 C1 145.02(16) . . . . ? 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 O6 H6A O7 0.84 2.12 2.954(3) 175.3 . O8 H8A O2 0.85 1.97 2.757(2) 153.1 . O5 H5A O2 0.86 1.87 2.7230(18) 176.0 . O4 H4B O5 0.84 1.89 2.725(2) 174.8 . O4 H4A O7 0.85 2.12 2.943(2) 162.6 . O6 H6B' O5 0.85 2.31 3.096(3) 153.7 5_655 O6 H6B O6 0.86 2.02 2.875(4) 175.9 5_655 O7 H7B O8 0.85 2.25 3.096(2) 171.3 1_655 O7 H7A O3 0.85 2.17 2.960(2) 154.6 6_656 O5 H5B O3 0.85 1.94 2.7948(17) 176.8 8_655 N1 H1A O6 0.82 2.17 2.9823(19) 171.9 4_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.382 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.055 # Attachment '- 12.cif' data_12 _database_code_depnum_ccdc_archive 'CCDC 853359' #TrackingRef '- 12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Cd N6 O15' _chemical_formula_weight 835.06 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.1093(11) _cell_length_b 19.192(2) _cell_length_c 17.7243(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3438.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6144 _cell_measurement_theta_min 2.298 _cell_measurement_theta_max 28.129 _exptl_crystal_description bar _exptl_crystal_colour orange _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.716 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7342 _exptl_absorpt_correction_T_max 0.9190 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 13624 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3041 _reflns_number_gt 2596 _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^)+(0.0322P)^2^+1.9902P] 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 3041 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0061(2) 0.19697(13) 0.08492(13) 0.0342(5) Uani 1 1 d . . . C2 C 1.0634(3) 0.20384(15) 0.01407(14) 0.0443(6) Uani 1 1 d . . . H2 H 1.0538 0.1686 -0.0215 0.053 Uiso 1 1 calc R . . C3 C 1.1342(3) 0.26286(15) -0.00335(15) 0.0497(7) Uani 1 1 d . . . H3 H 1.1741 0.2671 -0.0504 0.060 Uiso 1 1 calc R . . C4 C 1.1462(3) 0.31559(14) 0.04857(15) 0.0462(6) Uani 1 1 d . . . H4 H 1.1941 0.3555 0.0366 0.055 Uiso 1 1 calc R . . C5 C 1.0871(2) 0.30943(12) 0.11872(14) 0.0356(5) Uani 1 1 d . . . H5 H 1.0944 0.3458 0.1531 0.043 Uiso 1 1 calc R . . C6 C 1.0172(2) 0.24981(12) 0.13881(13) 0.0289(5) Uani 1 1 d . . . C7 C 0.9498(2) 0.24165(11) 0.21490(13) 0.0267(5) Uani 1 1 d . . . C8 C 0.8229(2) 0.28639(11) 0.21552(14) 0.0313(5) Uani 1 1 d . . . C9 C 0.9300(2) 0.16343(11) 0.23202(12) 0.0276(5) Uani 1 1 d . . . H9 H 0.8631 0.1578 0.2715 0.033 Uiso 1 1 calc R . . C10 C 0.9048(2) 0.11281(12) 0.17014(14) 0.0337(5) Uani 1 1 d . . . C11 C 0.5606(2) 0.12722(12) 0.16272(13) 0.0364(5) Uani 1 1 d . . . H11 H 0.6259 0.1280 0.1997 0.044 Uiso 1 1 calc R . . C12 C 0.5602(2) 0.07306(12) 0.11265(14) 0.0386(6) Uani 1 1 d . . . H12 H 0.6239 0.0382 0.1150 0.046 Uiso 1 1 calc R . . C13 C 0.4625(2) 0.07178(12) 0.05869(14) 0.0362(6) Uani 1 1 d . . . C14 C 0.3690(2) 0.12420(13) 0.05687(14) 0.0425(6) Uani 1 1 d . . . H14 H 0.3016 0.1238 0.0212 0.051 Uiso 1 1 calc R . . C15 C 0.3781(2) 0.17695(12) 0.10917(14) 0.0367(6) Uani 1 1 d . . . H15 H 0.3157 0.2126 0.1078 0.044 Uiso 1 1 calc R . . N3 N 0.4510(2) 0.01819(11) 0.00289(13) 0.0470(5) Uani 1 1 d . . . Cd1 Cd 0.5000 0.269524(11) 0.2500 0.02796(9) Uani 1 2 d S . . N1 N 0.9388(2) 0.13392(10) 0.10093(11) 0.0400(5) Uani 1 1 d . . . H1 H 0.9184 0.1074 0.0636 0.048 Uiso 1 1 calc R . . N2 N 0.47203(18) 0.17934(10) 0.16158(11) 0.0321(4) Uani 1 1 d . . . O1 O 0.71795(16) 0.25321(9) 0.22292(12) 0.0471(4) Uani 1 1 d . . . O2 O 0.83255(17) 0.35027(8) 0.20670(12) 0.0540(5) Uani 1 1 d . . . O3 O 0.85695(17) 0.05485(8) 0.18304(10) 0.0460(4) Uani 1 1 d . . . O4 O 0.4384(2) 0.35342(10) 0.16592(11) 0.0560(5) Uani 1 1 d . . . O5 O 0.0000 0.45774(19) 0.2500 0.1076(15) Uani 1 2 d S . . O6 O 0.2774(3) 0.48042(13) 0.17787(14) 0.0898(8) Uani 1 1 d . . . O7 O 0.6587(2) 0.42204(10) 0.11657(11) 0.0607(5) Uani 1 1 d . . . O8 O 0.3681(2) 0.47086(12) 0.01682(13) 0.0780(7) Uani 1 1 d . . . H4A H 0.5017 0.3770 0.1477 0.117 Uiso 1 1 d R . . H7A H 0.7155 0.4012 0.1443 0.117 Uiso 1 1 d R . . H7B H 0.6566 0.4639 0.1325 0.117 Uiso 1 1 d R . . H6A H 0.3005 0.5060 0.2145 0.117 Uiso 1 1 d R . . H4B H 0.3754 0.3784 0.1828 0.117 Uiso 1 1 d R . . H8B H 0.3689 0.5108 -0.0039 0.117 Uiso 1 1 d R . . H5B H -0.0498 0.4316 0.2230 0.117 Uiso 1 1 d R . . H6B H 0.1933 0.4786 0.1850 0.117 Uiso 1 1 d R . . H8A H 0.3463 0.4807 0.0619 0.117 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0301(12) 0.0365(12) 0.0359(13) 0.0018(11) -0.0044(10) 0.0059(10) C2 0.0436(15) 0.0571(17) 0.0323(14) -0.0025(12) -0.0040(12) 0.0108(13) C3 0.0427(16) 0.072(2) 0.0340(14) 0.0150(14) 0.0030(12) 0.0075(13) C4 0.0409(14) 0.0511(16) 0.0468(16) 0.0196(13) -0.0010(12) -0.0032(12) C5 0.0293(12) 0.0345(13) 0.0430(14) 0.0068(11) -0.0030(11) 0.0002(10) C6 0.0205(11) 0.0326(11) 0.0335(12) 0.0023(10) -0.0020(9) 0.0038(9) C7 0.0200(10) 0.0241(11) 0.0360(13) -0.0005(9) -0.0018(10) 0.0001(9) C8 0.0271(12) 0.0316(12) 0.0352(12) -0.0032(10) -0.0013(10) 0.0021(10) C9 0.0218(11) 0.0260(11) 0.0351(13) -0.0001(9) 0.0006(9) -0.0007(9) C10 0.0243(11) 0.0304(12) 0.0463(15) -0.0027(11) -0.0062(10) 0.0030(9) C11 0.0307(12) 0.0420(14) 0.0364(13) -0.0043(11) -0.0057(11) 0.0052(11) C12 0.0351(13) 0.0370(13) 0.0437(14) -0.0048(11) -0.0033(12) 0.0086(11) C13 0.0326(12) 0.0353(13) 0.0408(14) -0.0076(11) -0.0005(11) 0.0020(10) C14 0.0331(13) 0.0474(15) 0.0470(15) -0.0115(12) -0.0127(11) 0.0060(11) C15 0.0320(12) 0.0364(13) 0.0418(14) -0.0041(11) -0.0035(11) 0.0092(10) N3 0.0429(12) 0.0450(12) 0.0531(13) -0.0174(11) -0.0116(11) 0.0090(9) Cd1 0.02190(13) 0.02852(14) 0.03346(15) 0.000 0.00154(10) 0.000 N1 0.0456(12) 0.0360(11) 0.0385(12) -0.0110(9) -0.0047(10) -0.0019(10) N2 0.0284(10) 0.0352(11) 0.0325(10) -0.0019(8) 0.0001(8) 0.0035(8) O1 0.0206(9) 0.0439(9) 0.0769(13) -0.0021(9) 0.0059(9) 0.0002(8) O2 0.0380(10) 0.0293(9) 0.0947(15) 0.0050(10) -0.0079(10) 0.0065(8) O3 0.0495(10) 0.0271(9) 0.0614(12) -0.0033(8) -0.0065(9) -0.0093(8) O4 0.0630(13) 0.0506(11) 0.0545(12) 0.0110(9) -0.0032(10) 0.0090(10) O5 0.134(4) 0.051(2) 0.138(4) 0.000 -0.064(3) 0.000 O6 0.0938(18) 0.0956(19) 0.0800(17) -0.0137(14) -0.0016(14) 0.0011(15) O7 0.0711(14) 0.0441(11) 0.0668(13) -0.0027(10) -0.0166(11) 0.0061(10) O8 0.1002(19) 0.0708(15) 0.0630(14) -0.0052(11) 0.0044(13) 0.0069(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.389(3) . ? C1 C6 1.398(3) . ? C1 N1 1.417(3) . ? C2 C3 1.375(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C7 1.519(3) . ? C7 C8 1.544(3) . ? C7 C9 1.544(3) . ? C7 C7 1.606(4) 3_755 ? C8 O2 1.240(3) . ? C8 O1 1.244(3) . ? C9 C10 1.487(3) . ? C9 C9 1.551(4) 3_755 ? C9 H9 0.9800 . ? C10 O3 1.234(3) . ? C10 N1 1.337(3) . ? C11 N2 1.342(3) . ? C11 C12 1.367(3) . ? C11 H11 0.9300 . ? C12 C13 1.375(3) . ? C12 H12 0.9300 . ? C13 C14 1.381(3) . ? C13 N3 1.432(3) . ? C14 C15 1.376(3) . ? C14 H14 0.9300 . ? C15 N2 1.329(3) . ? C15 H15 0.9300 . ? N3 N3 1.217(4) 5_655 ? Cd1 O1 2.2766(17) . ? Cd1 O1 2.2766(17) 3_655 ? Cd1 O4 2.2805(18) 3_655 ? Cd1 O4 2.2805(18) . ? Cd1 N2 2.3520(19) . ? Cd1 N2 2.3520(19) 3_655 ? N1 H1 0.8600 . ? O4 H4A 0.8474 . ? O4 H4B 0.8522 . ? O5 H5B 0.8576 . ? O6 H6A 0.8478 . ? O6 H6B 0.8594 . ? O7 H7A 0.8552 . ? O7 H7B 0.8518 . ? O8 H8B 0.8500 . ? O8 H8A 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.0(2) . . ? C2 C1 N1 117.5(2) . . ? C6 C1 N1 121.4(2) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 117.5(2) . . ? C5 C6 C7 122.7(2) . . ? C1 C6 C7 119.7(2) . . ? C6 C7 C8 108.76(18) . . ? C6 C7 C9 109.42(18) . . ? C8 C7 C9 115.59(18) . . ? C6 C7 C7 113.8(2) . 3_755 ? C8 C7 C7 121.3(2) . 3_755 ? C9 C7 C7 85.96(12) . 3_755 ? O2 C8 O1 125.9(2) . . ? O2 C8 C7 118.9(2) . . ? O1 C8 C7 115.12(19) . . ? C10 C9 C7 120.81(19) . . ? C10 C9 C9 117.36(18) . 3_755 ? C7 C9 C9 87.88(12) . 3_755 ? C10 C9 H9 109.7 . . ? C7 C9 H9 109.7 . . ? C9 C9 H9 109.7 3_755 . ? O3 C10 N1 122.9(2) . . ? O3 C10 C9 121.3(2) . . ? N1 C10 C9 115.8(2) . . ? N2 C11 C12 123.7(2) . . ? N2 C11 H11 118.1 . . ? C12 C11 H11 118.1 . . ? C11 C12 C13 117.9(2) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 N3 123.5(2) . . ? C14 C13 N3 116.8(2) . . ? C15 C14 C13 118.3(2) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? N2 C15 C14 123.0(2) . . ? N2 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? N3 N3 C13 113.8(3) 5_655 . ? O1 Cd1 O1 164.19(9) . 3_655 ? O1 Cd1 O4 88.32(7) . 3_655 ? O1 Cd1 O4 102.92(7) 3_655 3_655 ? O1 Cd1 O4 102.92(7) . . ? O1 Cd1 O4 88.32(7) 3_655 . ? O4 Cd1 O4 90.18(10) 3_655 . ? O1 Cd1 N2 82.80(7) . . ? O1 Cd1 N2 85.58(7) 3_655 . ? O4 Cd1 N2 171.04(7) 3_655 . ? O4 Cd1 N2 92.94(7) . . ? O1 Cd1 N2 85.58(7) . 3_655 ? O1 Cd1 N2 82.80(7) 3_655 3_655 ? O4 Cd1 N2 92.94(7) 3_655 3_655 ? O4 Cd1 N2 171.04(7) . 3_655 ? N2 Cd1 N2 85.23(9) . 3_655 ? C10 N1 C1 124.5(2) . . ? C10 N1 H1 117.8 . . ? C1 N1 H1 117.8 . . ? C15 N2 C11 117.5(2) . . ? C15 N2 Cd1 125.23(15) . . ? C11 N2 Cd1 117.27(15) . . ? C8 O1 Cd1 140.98(16) . . ? Cd1 O4 H4A 114.9 . . ? Cd1 O4 H4B 111.8 . . ? H4A O4 H4B 113.4 . . ? H6A O6 H6B 100.6 . . ? H7A O7 H7B 105.5 . . ? H8B O8 H8A 102.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.1(4) . . . . ? N1 C1 C2 C3 -177.5(2) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C1 -1.4(3) . . . . ? C4 C5 C6 C7 -179.3(2) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? N1 C1 C6 C5 178.8(2) . . . . ? C2 C1 C6 C7 178.1(2) . . . . ? N1 C1 C6 C7 -3.3(3) . . . . ? C5 C6 C7 C8 75.0(3) . . . . ? C1 C6 C7 C8 -102.8(2) . . . . ? C5 C6 C7 C9 -157.9(2) . . . . ? C1 C6 C7 C9 24.3(3) . . . . ? C5 C6 C7 C7 -63.7(2) . . . 3_755 ? C1 C6 C7 C7 118.56(17) . . . 3_755 ? C6 C7 C8 O2 -60.8(3) . . . . ? C9 C7 C8 O2 175.7(2) . . . . ? C7 C7 C8 O2 74.2(3) 3_755 . . . ? C6 C7 C8 O1 117.2(2) . . . . ? C9 C7 C8 O1 -6.3(3) . . . . ? C7 C7 C8 O1 -107.8(2) 3_755 . . . ? C6 C7 C9 C10 -32.8(3) . . . . ? C8 C7 C9 C10 90.3(3) . . . . ? C7 C7 C9 C10 -146.7(2) 3_755 . . . ? C6 C7 C9 C9 88.1(2) . . . 3_755 ? C8 C7 C9 C9 -148.8(2) . . . 3_755 ? C7 C7 C9 C9 -25.8(2) 3_755 . . 3_755 ? C7 C9 C10 O3 -161.7(2) . . . . ? C9 C9 C10 O3 93.2(3) 3_755 . . . ? C7 C9 C10 N1 19.2(3) . . . . ? C9 C9 C10 N1 -85.9(2) 3_755 . . . ? N2 C11 C12 C13 -0.7(4) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C11 C12 C13 N3 179.9(2) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? N3 C13 C14 C15 -179.3(2) . . . . ? C13 C14 C15 N2 -0.6(4) . . . . ? C12 C13 N3 N3 -14.3(5) . . . 5_655 ? C14 C13 N3 N3 165.8(3) . . . 5_655 ? O3 C10 N1 C1 -173.3(2) . . . . ? C9 C10 N1 C1 5.8(3) . . . . ? C2 C1 N1 C10 164.3(2) . . . . ? C6 C1 N1 C10 -14.3(3) . . . . ? C14 C15 N2 C11 -0.3(4) . . . . ? C14 C15 N2 Cd1 177.48(19) . . . . ? C12 C11 N2 C15 1.0(4) . . . . ? C12 C11 N2 Cd1 -176.99(19) . . . . ? O1 Cd1 N2 C15 -139.00(19) . . . . ? O1 Cd1 N2 C15 51.74(19) 3_655 . . . ? O4 Cd1 N2 C15 -146.6(4) 3_655 . . . ? O4 Cd1 N2 C15 -36.34(19) . . . . ? N2 Cd1 N2 C15 134.9(2) 3_655 . . . ? O1 Cd1 N2 C11 38.81(17) . . . . ? O1 Cd1 N2 C11 -130.45(18) 3_655 . . . ? O4 Cd1 N2 C11 31.2(5) 3_655 . . . ? O4 Cd1 N2 C11 141.46(17) . . . . ? N2 Cd1 N2 C11 -47.33(15) 3_655 . . . ? O2 C8 O1 Cd1 -16.5(5) . . . . ? C7 C8 O1 Cd1 165.72(19) . . . . ? O1 Cd1 O1 C8 -172.8(3) 3_655 . . . ? O4 Cd1 O1 C8 -37.0(3) 3_655 . . . ? O4 Cd1 O1 C8 52.8(3) . . . . ? N2 Cd1 O1 C8 144.2(3) . . . . ? N2 Cd1 O1 C8 -130.1(3) 3_655 . . . ? 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 O4 H4A O7 0.85 1.89 2.731(3) 171.6 . O7 H7A O2 0.86 1.89 2.746(3) 176.1 . N1 H1 O8 0.86 2.13 2.985(3) 171.3 4 O7 H7B O3 0.85 1.97 2.812(3) 171.9 8_765 O6 H6A O3 0.85 2.12 2.961(3) 170.5 6_566 O4 H4B O6 0.85 2.20 2.939(3) 145.6 . O6 H6B O5 0.86 2.30 3.112(3) 156.8 . O8 H8A O6 0.85 2.17 3.004(3) 166.7 . O8 H8B O7 0.85 2.39 3.145(3) 147.7 5_665 O5 H5B O2 0.86 1.98 2.777(3) 153.5 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.370 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.053 # Attachment '- 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 853360' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Co N4 O8' _chemical_formula_weight 627.46 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 8.3646(15) _cell_length_b 9.7689(18) _cell_length_c 9.8696(18) _cell_angle_alpha 108.832(2) _cell_angle_beta 104.851(2) _cell_angle_gamma 107.612(2) _cell_volume 669.2(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2666 _cell_measurement_theta_min 2.371 _cell_measurement_theta_max 28.129 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 323 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8220 _exptl_absorpt_correction_T_max 0.9141 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 3539 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2449 _reflns_number_gt 2331 _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^)+(0.0509P)^2^+0.3476P] 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 2449 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7516(3) -0.0213(3) 0.3673(2) 0.0282(4) Uani 1 1 d . . . C2 C 0.6068(3) -0.0072(3) 0.2651(3) 0.0313(5) Uani 1 1 d . . . H2 H 0.5546 -0.0756 0.1595 0.038 Uiso 1 1 calc R . . C3 C 0.5450(3) 0.1032(3) 0.3192(2) 0.0281(4) Uani 1 1 d . . . C4 C 0.4014(3) 0.1232(3) 0.2070(2) 0.0309(5) Uani 1 1 d . . . C5 C 0.6164(3) 0.2055(2) 0.4831(2) 0.0280(4) Uani 1 1 d . . . C6 C 0.7498(3) 0.1857(2) 0.5837(2) 0.0276(4) Uani 1 1 d . . . C7 C 0.8220(3) 0.2783(3) 0.7446(3) 0.0345(5) Uani 1 1 d . . . H7 H 0.9100 0.2638 0.8108 0.041 Uiso 1 1 calc R . . C8 C 0.7612(4) 0.3908(3) 0.8035(3) 0.0417(6) Uani 1 1 d . . . H8 H 0.8080 0.4522 0.9105 0.050 Uiso 1 1 calc R . . C9 C 0.6305(3) 0.4145(3) 0.7055(3) 0.0436(6) Uani 1 1 d . . . H9 H 0.5913 0.4917 0.7470 0.052 Uiso 1 1 calc R . . C10 C 0.5601(3) 0.3240(3) 0.5483(3) 0.0369(5) Uani 1 1 d . . . H10 H 0.4736 0.3410 0.4833 0.044 Uiso 1 1 calc R . . H4A H -0.1637 -0.1641 0.1278 0.044 Uiso 1 1 d R . . H4B H -0.2571 -0.2134 -0.0227 0.044 Uiso 1 1 d R . . C11 C 0.1016(3) -0.2662(3) -0.1638(3) 0.0327(5) Uani 1 1 d . . . H11 H 0.1697 -0.2404 -0.0613 0.039 Uiso 1 1 calc R . . C12 C 0.1033(3) -0.3892(3) -0.2804(3) 0.0328(5) Uani 1 1 d . . . H12 H 0.1725 -0.4428 -0.2554 0.039 Uiso 1 1 calc R . . C13 C 0.0018(3) -0.4336(2) -0.4355(2) 0.0263(4) Uani 1 1 d . . . C14 C -0.0948(3) -0.3448(3) -0.4620(2) 0.0318(5) Uani 1 1 d . . . H14 H -0.1645 -0.3683 -0.5633 0.038 Uiso 1 1 calc R . . C15 C -0.0875(3) -0.2225(3) -0.3388(2) 0.0302(5) Uani 1 1 d . . . H15 H -0.1525 -0.1646 -0.3605 0.036 Uiso 1 1 calc R . . Co1 Co 0.0000 0.0000 0.0000 0.02359(15) Uani 1 2 d S . . N1 N 0.8123(2) 0.0739(2) 0.5212(2) 0.0292(4) Uani 1 1 d . . . H1 H 0.8956 0.0644 0.5846 0.035 Uiso 1 1 calc R . . N2 N 0.0078(2) -0.1818(2) -0.1896(2) 0.0275(4) Uani 1 1 d . . . O1 O 0.8235(2) -0.1132(2) 0.32168(18) 0.0357(4) Uani 1 1 d . . . O2 O 0.4536(2) 0.2403(2) 0.1795(3) 0.0576(6) Uani 1 1 d . . . O3 O 0.24126(19) 0.01919(17) 0.15312(17) 0.0301(3) Uani 1 1 d . . . O4 O -0.1507(2) -0.18780(18) 0.04102(17) 0.0313(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0261(10) 0.0336(11) 0.0269(11) 0.0137(9) 0.0095(9) 0.0152(9) C2 0.0282(11) 0.0360(11) 0.0231(10) 0.0085(9) 0.0042(8) 0.0152(9) C3 0.0213(10) 0.0323(11) 0.0281(11) 0.0132(9) 0.0056(8) 0.0115(8) C4 0.0282(11) 0.0375(12) 0.0242(11) 0.0092(9) 0.0053(9) 0.0189(10) C5 0.0230(10) 0.0300(11) 0.0293(11) 0.0124(9) 0.0077(8) 0.0117(8) C6 0.0255(10) 0.0298(10) 0.0278(11) 0.0133(9) 0.0094(9) 0.0121(9) C7 0.0348(12) 0.0396(12) 0.0268(11) 0.0139(10) 0.0074(9) 0.0171(10) C8 0.0458(14) 0.0410(13) 0.0289(12) 0.0071(10) 0.0111(11) 0.0181(11) C9 0.0445(14) 0.0377(13) 0.0440(15) 0.0085(11) 0.0154(12) 0.0231(11) C10 0.0314(11) 0.0389(12) 0.0383(13) 0.0136(10) 0.0087(10) 0.0197(10) C11 0.0376(12) 0.0349(11) 0.0227(10) 0.0068(9) 0.0086(9) 0.0204(10) C12 0.0385(12) 0.0333(11) 0.0271(11) 0.0079(9) 0.0111(9) 0.0227(10) C13 0.0260(10) 0.0252(10) 0.0254(10) 0.0069(9) 0.0124(8) 0.0105(8) C14 0.0363(11) 0.0344(11) 0.0215(10) 0.0062(9) 0.0092(9) 0.0191(10) C15 0.0334(11) 0.0308(11) 0.0249(11) 0.0074(9) 0.0099(9) 0.0180(9) Co1 0.0234(2) 0.0260(2) 0.0172(2) 0.00351(16) 0.00455(15) 0.01434(16) N1 0.0281(9) 0.0374(10) 0.0247(9) 0.0143(8) 0.0063(7) 0.0195(8) N2 0.0281(9) 0.0276(9) 0.0234(9) 0.0059(7) 0.0100(7) 0.0132(7) O1 0.0381(9) 0.0451(9) 0.0283(8) 0.0128(7) 0.0109(7) 0.0280(8) O2 0.0337(9) 0.0582(12) 0.0727(14) 0.0443(11) -0.0011(9) 0.0105(9) O3 0.0250(7) 0.0327(8) 0.0265(8) 0.0076(6) 0.0034(6) 0.0156(6) O4 0.0321(8) 0.0359(8) 0.0243(7) 0.0108(6) 0.0080(6) 0.0172(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.255(3) . ? C1 N1 1.356(3) . ? C1 C2 1.438(3) . ? C2 C3 1.350(3) . ? C2 H2 0.9300 . ? C3 C5 1.439(3) . ? C3 C4 1.519(3) . ? C4 O2 1.238(3) . ? C4 O3 1.254(3) . ? C5 C6 1.399(3) . ? C5 C10 1.407(3) . ? C6 N1 1.387(3) . ? C6 C7 1.398(3) . ? C7 C8 1.372(3) . ? C7 H7 0.9300 . ? C8 C9 1.392(4) . ? C8 H8 0.9300 . ? C9 C10 1.367(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 N2 1.337(3) . ? C11 C12 1.376(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(3) . ? C12 H12 0.9300 . ? C13 C14 1.391(3) . ? C13 C13 1.481(4) 2_544 ? C14 C15 1.374(3) . ? C14 H14 0.9300 . ? C15 N2 1.338(3) . ? C15 H15 0.9300 . ? Co1 O3 2.1014(14) . ? Co1 O3 2.1014(14) 2 ? Co1 O4 2.1119(16) 2 ? Co1 O4 2.1119(16) . ? Co1 N2 2.1553(17) . ? Co1 N2 2.1553(17) 2 ? N1 H1 0.8600 . ? O4 H4A 0.8568 . ? O4 H4B 0.8530 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 119.81(18) . . ? O1 C1 C2 124.0(2) . . ? N1 C1 C2 116.18(18) . . ? C3 C2 C1 121.5(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C5 120.71(19) . . ? C2 C3 C4 120.23(19) . . ? C5 C3 C4 119.05(18) . . ? O2 C4 O3 126.9(2) . . ? O2 C4 C3 117.07(19) . . ? O3 C4 C3 116.05(19) . . ? C6 C5 C10 118.0(2) . . ? C6 C5 C3 117.91(19) . . ? C10 C5 C3 124.1(2) . . ? N1 C6 C7 120.14(19) . . ? N1 C6 C5 118.86(19) . . ? C7 C6 C5 121.0(2) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.9(2) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 121.0(2) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? N2 C11 C12 123.7(2) . . ? N2 C11 H11 118.1 . . ? C12 C11 H11 118.1 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 115.86(19) . . ? C12 C13 C13 122.0(2) . 2_544 ? C14 C13 C13 122.1(2) . 2_544 ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? N2 C15 C14 123.8(2) . . ? N2 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? O3 Co1 O3 180.00(9) . 2 ? O3 Co1 O4 90.84(6) . 2 ? O3 Co1 O4 89.16(6) 2 2 ? O3 Co1 O4 89.16(6) . . ? O3 Co1 O4 90.84(6) 2 . ? O4 Co1 O4 180.00(7) 2 . ? O3 Co1 N2 90.34(6) . . ? O3 Co1 N2 89.66(6) 2 . ? O4 Co1 N2 93.65(6) 2 . ? O4 Co1 N2 86.35(6) . . ? O3 Co1 N2 89.66(6) . 2 ? O3 Co1 N2 90.34(6) 2 2 ? O4 Co1 N2 86.35(6) 2 2 ? O4 Co1 N2 93.65(6) . 2 ? N2 Co1 N2 180.00(10) . 2 ? C1 N1 C6 124.72(17) . . ? C1 N1 H1 117.6 . . ? C6 N1 H1 117.6 . . ? C11 N2 C15 116.12(18) . . ? C11 N2 Co1 121.33(14) . . ? C15 N2 Co1 122.46(14) . . ? C4 O3 Co1 129.60(14) . . ? Co1 O4 H4A 118.1 . . ? Co1 O4 H4B 99.1 . . ? H4A O4 H4B 102.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -174.3(2) . . . . ? N1 C1 C2 C3 4.7(3) . . . . ? C1 C2 C3 C5 -3.2(3) . . . . ? C1 C2 C3 C4 175.61(19) . . . . ? C2 C3 C4 O2 -104.4(3) . . . . ? C5 C3 C4 O2 74.4(3) . . . . ? C2 C3 C4 O3 76.3(3) . . . . ? C5 C3 C4 O3 -104.9(2) . . . . ? C2 C3 C5 C6 -0.6(3) . . . . ? C4 C3 C5 C6 -179.37(19) . . . . ? C2 C3 C5 C10 179.5(2) . . . . ? C4 C3 C5 C10 0.7(3) . . . . ? C10 C5 C6 N1 -177.48(19) . . . . ? C3 C5 C6 N1 2.6(3) . . . . ? C10 C5 C6 C7 1.5(3) . . . . ? C3 C5 C6 C7 -178.4(2) . . . . ? N1 C6 C7 C8 178.4(2) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C5 0.6(4) . . . . ? C6 C5 C10 C9 -1.5(3) . . . . ? C3 C5 C10 C9 178.4(2) . . . . ? N2 C11 C12 C13 -0.8(4) . . . . ? C11 C12 C13 C14 1.2(3) . . . . ? C11 C12 C13 C13 -179.3(2) . . . 2_544 ? C12 C13 C14 C15 -0.5(3) . . . . ? C13 C13 C14 C15 -180.0(2) 2_544 . . . ? C13 C14 C15 N2 -0.7(4) . . . . ? O1 C1 N1 C6 176.43(19) . . . . ? C2 C1 N1 C6 -2.6(3) . . . . ? C7 C6 N1 C1 -179.9(2) . . . . ? C5 C6 N1 C1 -1.0(3) . . . . ? C12 C11 N2 C15 -0.3(3) . . . . ? C12 C11 N2 Co1 176.38(18) . . . . ? C14 C15 N2 C11 1.1(3) . . . . ? C14 C15 N2 Co1 -175.57(17) . . . . ? O3 Co1 N2 C11 21.45(17) . . . . ? O3 Co1 N2 C11 -158.55(17) 2 . . . ? O4 Co1 N2 C11 112.31(17) 2 . . . ? O4 Co1 N2 C11 -67.69(17) . . . . ? N2 Co1 N2 C11 -45(100) 2 . . . ? O3 Co1 N2 C15 -162.07(17) . . . . ? O3 Co1 N2 C15 17.93(17) 2 . . . ? O4 Co1 N2 C15 -71.20(17) 2 . . . ? O4 Co1 N2 C15 108.80(17) . . . . ? N2 Co1 N2 C15 132(100) 2 . . . ? O2 C4 O3 Co1 -0.6(4) . . . . ? C3 C4 O3 Co1 178.60(13) . . . . ? O3 Co1 O3 C4 -119(100) 2 . . . ? O4 Co1 O3 C4 8.83(18) 2 . . . ? O4 Co1 O3 C4 -171.17(18) . . . . ? N2 Co1 O3 C4 102.49(18) . . . . ? N2 Co1 O3 C4 -77.51(18) 2 . . . ? 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 N1 H1 O1 0.86 2.13 2.885(2) 146.5 2_756 O4 H4B O2 0.85 1.83 2.662(2) 165.9 2 O4 H4A O1 0.86 1.86 2.711(2) 176.0 1_455 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.597 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.084 # Attachment '- 3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 853361' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Mn N4 O8' _chemical_formula_weight 623.47 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' Mn Mn 0.3368 0.7283 '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 8.4711(14) _cell_length_b 9.7326(15) _cell_length_c 9.8148(16) _cell_angle_alpha 107.072(2) _cell_angle_beta 104.858(2) _cell_angle_gamma 107.854(2) _cell_volume 680.83(19) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2632 _cell_measurement_theta_min 2.590 _cell_measurement_theta_max 28.198 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 321 _exptl_absorpt_coefficient_mu 0.546 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8533 _exptl_absorpt_correction_T_max 0.8801 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 3622 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.60 _reflns_number_total 2494 _reflns_number_gt 2337 _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^)+(0.0730P)^2^+0.2240P] 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 2494 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8247(3) 0.7790(3) 0.7416(3) 0.0366(5) Uani 1 1 d . . . H1 H 0.9138 0.7661 0.8080 0.044 Uiso 1 1 calc R . . C2 C 0.7633(3) 0.8899(3) 0.7977(3) 0.0435(6) Uani 1 1 d . . . H2 H 0.8107 0.9514 0.9030 0.052 Uiso 1 1 calc R . . C3 C 0.6316(3) 0.9119(3) 0.7000(3) 0.0451(6) Uani 1 1 d . . . H3 H 0.5922 0.9884 0.7397 0.054 Uiso 1 1 calc R . . C4 C 0.5596(3) 0.8201(3) 0.5444(3) 0.0386(5) Uani 1 1 d . . . H4 H 0.4717 0.8353 0.4791 0.046 Uiso 1 1 calc R . . C5 C 0.6171(3) 0.7039(2) 0.4827(2) 0.0293(4) Uani 1 1 d . . . C6 C 0.5451(3) 0.6017(2) 0.3213(2) 0.0293(4) Uani 1 1 d . . . C7 C 0.6069(3) 0.4922(3) 0.2704(2) 0.0325(5) Uani 1 1 d . . . H7 H 0.5545 0.4238 0.1667 0.039 Uiso 1 1 calc R . . C8 C 0.7518(3) 0.4786(2) 0.3721(2) 0.0292(4) Uani 1 1 d . . . C9 C 0.7516(3) 0.6856(2) 0.5832(2) 0.0281(4) Uani 1 1 d . . . C10 C 0.4030(3) 0.6218(2) 0.2084(2) 0.0324(5) Uani 1 1 d . . . C11 C 0.1091(3) 0.2326(3) -0.1686(2) 0.0363(5) Uani 1 1 d . . . H11 H 0.1811 0.2600 -0.0673 0.044 Uiso 1 1 calc R . . C12 C 0.1091(3) 0.1110(3) -0.2834(3) 0.0360(5) Uani 1 1 d . . . H12 H 0.1804 0.0589 -0.2587 0.043 Uiso 1 1 calc R . . C13 C 0.0028(3) 0.0655(2) -0.4364(2) 0.0276(4) Uani 1 1 d . . . C14 C -0.0977(3) 0.1511(2) -0.4630(2) 0.0345(5) Uani 1 1 d . . . H14 H -0.1709 0.1265 -0.5631 0.041 Uiso 1 1 calc R . . C15 C -0.0887(3) 0.2722(2) -0.3414(2) 0.0337(5) Uani 1 1 d . . . H15 H -0.1562 0.3282 -0.3628 0.040 Uiso 1 1 calc R . . Mn1 Mn 0.0000 0.5000 0.0000 0.02586(17) Uani 1 2 d S . . N1 N 0.8136(2) 0.5751(2) 0.52355(19) 0.0301(4) Uani 1 1 d . . . H1A H 0.9044 0.5769 0.5789 0.036 Uiso 1 1 d R . . N2 N 0.0113(2) 0.3138(2) -0.1945(2) 0.0306(4) Uani 1 1 d . . . O1 O 0.8229(2) 0.38777(19) 0.32859(17) 0.0374(4) Uani 1 1 d . . . O2 O 0.4527(2) 0.7390(2) 0.1794(3) 0.0631(6) Uani 1 1 d . . . O3 O 0.24572(19) 0.51840(17) 0.15632(17) 0.0342(4) Uani 1 1 d . . . O4 O 0.1609(2) 0.69734(17) -0.04463(17) 0.0353(4) Uani 1 1 d . . . H4A H 0.2582 0.7255 0.0295 0.053 Uiso 1 1 d R . . H4B H 0.1698 0.6734 -0.1324 0.053 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0363(12) 0.0411(12) 0.0299(11) 0.0145(9) 0.0078(10) 0.0166(10) C2 0.0485(14) 0.0427(13) 0.0318(11) 0.0088(10) 0.0130(11) 0.0174(11) C3 0.0463(14) 0.0413(13) 0.0481(14) 0.0112(11) 0.0198(12) 0.0238(11) C4 0.0332(12) 0.0414(12) 0.0420(12) 0.0152(10) 0.0111(10) 0.0207(10) C5 0.0238(10) 0.0329(10) 0.0315(10) 0.0142(9) 0.0090(9) 0.0122(8) C6 0.0222(10) 0.0331(10) 0.0315(11) 0.0138(9) 0.0071(8) 0.0119(8) C7 0.0279(11) 0.0390(11) 0.0265(10) 0.0107(9) 0.0053(9) 0.0152(9) C8 0.0261(10) 0.0349(10) 0.0287(10) 0.0138(8) 0.0094(8) 0.0152(9) C9 0.0253(10) 0.0319(10) 0.0289(10) 0.0142(8) 0.0111(8) 0.0116(8) C10 0.0287(11) 0.0379(12) 0.0283(10) 0.0103(9) 0.0057(9) 0.0180(9) C11 0.0390(12) 0.0361(11) 0.0274(10) 0.0035(9) 0.0088(9) 0.0194(10) C12 0.0394(12) 0.0362(11) 0.0314(11) 0.0062(9) 0.0119(10) 0.0229(10) C13 0.0280(10) 0.0258(9) 0.0279(10) 0.0070(8) 0.0145(8) 0.0101(8) C14 0.0405(12) 0.0350(11) 0.0261(10) 0.0062(8) 0.0109(9) 0.0207(10) C15 0.0374(12) 0.0327(11) 0.0303(11) 0.0070(9) 0.0129(9) 0.0192(9) Mn1 0.0243(3) 0.0283(3) 0.0205(2) 0.00303(17) 0.00484(18) 0.01484(18) N1 0.0267(9) 0.0396(10) 0.0264(9) 0.0140(7) 0.0067(7) 0.0187(8) N2 0.0319(9) 0.0290(9) 0.0275(9) 0.0050(7) 0.0125(8) 0.0134(7) O1 0.0367(9) 0.0480(9) 0.0318(8) 0.0136(7) 0.0102(7) 0.0275(7) O2 0.0367(10) 0.0638(12) 0.0794(14) 0.0484(11) -0.0029(9) 0.0110(9) O3 0.0269(8) 0.0353(8) 0.0317(8) 0.0083(6) 0.0015(6) 0.0148(6) O4 0.0354(8) 0.0418(8) 0.0280(7) 0.0128(6) 0.0084(6) 0.0193(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(3) . ? C1 C9 1.399(3) . ? C1 H1 0.9300 . ? C2 C3 1.389(4) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.404(3) . ? C4 H4 0.9300 . ? C5 C9 1.398(3) . ? C5 C6 1.441(3) . ? C6 C7 1.351(3) . ? C6 C10 1.517(3) . ? C7 C8 1.439(3) . ? C7 H7 0.9300 . ? C8 O1 1.251(2) . ? C8 N1 1.358(3) . ? C9 N1 1.382(3) . ? C10 O2 1.232(3) . ? C10 O3 1.256(3) . ? C11 N2 1.336(3) . ? C11 C12 1.374(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(3) . ? C12 H12 0.9300 . ? C13 C14 1.392(3) . ? C13 C13 1.478(4) 2_554 ? C14 C15 1.375(3) . ? C14 H14 0.9300 . ? C15 N2 1.334(3) . ? C15 H15 0.9300 . ? Mn1 O3 2.1659(14) . ? Mn1 O3 2.1659(14) 2_565 ? Mn1 O4 2.2212(15) 2_565 ? Mn1 O4 2.2212(15) . ? Mn1 N2 2.2601(17) 2_565 ? Mn1 N2 2.2601(17) . ? N1 H1A 0.8117 . ? O4 H4A 0.8487 . ? O4 H4B 0.8536 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 119.2(2) . . ? C2 C1 H1 120.4 . . ? C9 C1 H1 120.4 . . ? C1 C2 C3 121.2(2) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C9 C5 C4 118.3(2) . . ? C9 C5 C6 117.95(19) . . ? C4 C5 C6 123.73(19) . . ? C7 C6 C5 120.42(18) . . ? C7 C6 C10 120.25(18) . . ? C5 C6 C10 119.30(18) . . ? C6 C7 C8 121.76(19) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? O1 C8 N1 120.01(18) . . ? O1 C8 C7 124.13(19) . . ? N1 C8 C7 115.84(18) . . ? N1 C9 C5 118.96(18) . . ? N1 C9 C1 120.30(19) . . ? C5 C9 C1 120.7(2) . . ? O2 C10 O3 126.59(19) . . ? O2 C10 C6 116.99(19) . . ? O3 C10 C6 116.41(18) . . ? N2 C11 C12 123.6(2) . . ? N2 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 120.2(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 116.08(18) . . ? C12 C13 C13 122.1(2) . 2_554 ? C14 C13 C13 121.8(2) . 2_554 ? C15 C14 C13 119.99(19) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? N2 C15 C14 123.7(2) . . ? N2 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? O3 Mn1 O3 180.0 . 2_565 ? O3 Mn1 O4 90.76(6) . 2_565 ? O3 Mn1 O4 89.24(6) 2_565 2_565 ? O3 Mn1 O4 89.24(6) . . ? O3 Mn1 O4 90.76(6) 2_565 . ? O4 Mn1 O4 180.00(7) 2_565 . ? O3 Mn1 N2 89.94(6) . 2_565 ? O3 Mn1 N2 90.06(6) 2_565 2_565 ? O4 Mn1 N2 93.33(6) 2_565 2_565 ? O4 Mn1 N2 86.67(6) . 2_565 ? O3 Mn1 N2 90.06(6) . . ? O3 Mn1 N2 89.94(6) 2_565 . ? O4 Mn1 N2 86.67(6) 2_565 . ? O4 Mn1 N2 93.33(6) . . ? N2 Mn1 N2 180.0 2_565 . ? C8 N1 C9 124.93(17) . . ? C8 N1 H1A 115.8 . . ? C9 N1 H1A 118.5 . . ? C15 N2 C11 116.42(18) . . ? C15 N2 Mn1 121.45(14) . . ? C11 N2 Mn1 121.99(14) . . ? C10 O3 Mn1 129.95(13) . . ? Mn1 O4 H4A 95.9 . . ? Mn1 O4 H4B 116.7 . . ? H4A O4 H4B 113.6 . . ? 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 C9 C1 C2 C3 -0.7(4) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C9 -1.1(3) . . . . ? C3 C4 C5 C6 178.8(2) . . . . ? C9 C5 C6 C7 -0.1(3) . . . . ? C4 C5 C6 C7 -179.9(2) . . . . ? C9 C5 C6 C10 -178.12(18) . . . . ? C4 C5 C6 C10 2.0(3) . . . . ? C5 C6 C7 C8 -3.3(3) . . . . ? C10 C6 C7 C8 174.77(18) . . . . ? C6 C7 C8 O1 -174.2(2) . . . . ? C6 C7 C8 N1 4.3(3) . . . . ? C4 C5 C9 N1 -177.93(18) . . . . ? C6 C5 C9 N1 2.2(3) . . . . ? C4 C5 C9 C1 1.1(3) . . . . ? C6 C5 C9 C1 -178.77(19) . . . . ? C2 C1 C9 N1 178.8(2) . . . . ? C2 C1 C9 C5 -0.2(3) . . . . ? C7 C6 C10 O2 -105.7(3) . . . . ? C5 C6 C10 O2 72.3(3) . . . . ? C7 C6 C10 O3 75.6(3) . . . . ? C5 C6 C10 O3 -106.3(2) . . . . ? N2 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C11 C12 C13 C13 -179.5(2) . . . 2_554 ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C13 C14 C15 180.0(2) 2_554 . . . ? C13 C14 C15 N2 -0.8(4) . . . . ? O1 C8 N1 C9 176.49(18) . . . . ? C7 C8 N1 C9 -2.1(3) . . . . ? C5 C9 N1 C8 -1.1(3) . . . . ? C1 C9 N1 C8 179.88(19) . . . . ? C14 C15 N2 C11 1.3(3) . . . . ? C14 C15 N2 Mn1 -174.62(17) . . . . ? C12 C11 N2 C15 -0.7(3) . . . . ? C12 C11 N2 Mn1 175.15(18) . . . . ? O3 Mn1 N2 C15 -164.85(17) . . . . ? O3 Mn1 N2 C15 15.15(17) 2_565 . . . ? O4 Mn1 N2 C15 104.38(17) 2_565 . . . ? O4 Mn1 N2 C15 -75.62(17) . . . . ? N2 Mn1 N2 C15 -106(78) 2_565 . . . ? O3 Mn1 N2 C11 19.47(17) . . . . ? O3 Mn1 N2 C11 -160.53(17) 2_565 . . . ? O4 Mn1 N2 C11 -71.30(17) 2_565 . . . ? O4 Mn1 N2 C11 108.70(17) . . . . ? N2 Mn1 N2 C11 78(78) 2_565 . . . ? O2 C10 O3 Mn1 -0.5(3) . . . . ? C6 C10 O3 Mn1 177.99(13) . . . . ? O3 Mn1 O3 C10 79(100) 2_565 . . . ? O4 Mn1 O3 C10 -170.48(17) 2_565 . . . ? O4 Mn1 O3 C10 9.52(17) . . . . ? N2 Mn1 O3 C10 -77.14(18) 2_565 . . . ? N2 Mn1 O3 C10 102.86(18) . . . . ? 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 N1 H1A O1 0.81 2.13 2.904(2) 159.8 2_766 O4 H4A O2 0.85 1.85 2.680(2) 167.2 . O4 H4A O3 0.85 2.65 3.082(2) 112.8 . O4 H4B O1 0.85 1.86 2.717(2) 176.9 2_665 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.60 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.486 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.098 # Attachment '- 4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 853362' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Cd N4 O8' _chemical_formula_weight 680.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5836(18) _cell_length_b 9.657(2) _cell_length_c 9.767(2) _cell_angle_alpha 106.032(2) _cell_angle_beta 104.659(2) _cell_angle_gamma 107.781(3) _cell_volume 688.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2543 _cell_measurement_theta_min 2.398 _cell_measurement_theta_max 27.932 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8615 _exptl_absorpt_correction_T_max 0.8755 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 3627 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2505 _reflns_number_gt 2462 _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^)+(0.0387P)^2^+0.3848P] 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 2505 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5965(4) 0.8835(4) 0.7906(3) 0.0345(6) Uani 1 1 d . . . C2 C 0.4539(3) 0.9016(3) 0.6776(3) 0.0312(6) Uani 1 1 d . . . C3 C 0.3911(4) 1.0097(3) 0.7265(3) 0.0336(6) Uani 1 1 d . . . H3 H 0.4430 1.0789 0.8287 0.040 Uiso 1 1 calc R . . C4 C 0.2458(4) 1.0213(3) 0.6252(3) 0.0316(6) Uani 1 1 d . . . C5 C 0.2463(3) 0.8133(3) 0.4174(3) 0.0305(6) Uani 1 1 d . . . C6 C 0.1735(4) 0.7181(4) 0.2617(3) 0.0379(6) Uani 1 1 d . . . H6 H 0.0835 0.7294 0.1955 0.045 Uiso 1 1 calc R . . C7 C 0.2350(4) 0.6080(4) 0.2070(4) 0.0444(7) Uani 1 1 d . . . H7 H 0.1865 0.5444 0.1032 0.053 Uiso 1 1 calc R . . C8 C 0.3704(4) 0.5899(4) 0.3056(4) 0.0465(8) Uani 1 1 d . . . H8 H 0.4118 0.5149 0.2674 0.056 Uiso 1 1 calc R . . C9 C 0.4415(4) 0.6830(4) 0.4583(4) 0.0408(7) Uani 1 1 d . . . H9 H 0.5306 0.6698 0.5236 0.049 Uiso 1 1 calc R . . C10 C 0.3826(3) 0.7978(3) 0.5181(3) 0.0307(6) Uani 1 1 d . . . C11 C 1.0906(4) 1.2309(3) 1.3418(3) 0.0356(6) Uani 1 1 d . . . H11 H 1.1603 1.1764 1.3623 0.043 Uiso 1 1 calc R . . C12 C 1.1001(4) 1.3516(4) 1.4626(3) 0.0374(6) Uani 1 1 d . . . H12 H 1.1756 1.3776 1.5614 0.045 Uiso 1 1 calc R . . C13 C 0.9968(4) 1.4345(3) 1.4365(3) 0.0302(6) Uani 1 1 d . . . C14 C 0.8865(4) 1.3873(4) 1.2866(3) 0.0394(7) Uani 1 1 d . . . H14 H 0.8130 1.4379 1.2633 0.047 Uiso 1 1 calc R . . C15 C 0.8853(4) 1.2652(4) 1.1712(3) 0.0404(7) Uani 1 1 d . . . H15 H 0.8103 1.2358 1.0713 0.049 Uiso 1 1 calc R . . N1 N 0.1835(3) 0.9228(3) 0.4757(3) 0.0324(5) Uani 1 1 d . . . H1 H 0.0984 0.9293 0.4125 0.039 Uiso 1 1 calc R . . N2 N 0.9870(3) 1.1879(3) 1.1971(3) 0.0328(5) Uani 1 1 d . . . O1 O 0.7480(3) 0.9864(3) 0.8365(2) 0.0400(5) Uani 1 1 d . . . O2 O 0.5514(3) 0.7672(3) 0.8240(3) 0.0699(8) Uani 1 1 d . . . O3 O 0.1753(3) 1.1125(3) 0.6675(2) 0.0395(5) Uani 1 1 d . . . O4 O 0.8289(3) 0.7873(2) 1.0447(2) 0.0383(5) Uani 1 1 d . . . H4A H 0.7269 0.7599 0.9744 0.057 Uiso 1 1 d R . . H4B H 0.8236 0.8220 1.1335 0.057 Uiso 1 1 d R . . Cd1 Cd 1.0000 1.0000 1.0000 0.02850(11) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0318(15) 0.0404(17) 0.0289(13) 0.0097(12) 0.0041(12) 0.0205(13) C2 0.0231(13) 0.0368(15) 0.0322(14) 0.0153(12) 0.0042(11) 0.0131(11) C3 0.0298(14) 0.0400(16) 0.0266(13) 0.0101(12) 0.0028(11) 0.0169(12) C4 0.0290(14) 0.0353(15) 0.0318(14) 0.0140(12) 0.0092(11) 0.0149(12) C5 0.0266(13) 0.0342(15) 0.0319(14) 0.0153(12) 0.0089(11) 0.0127(11) C6 0.0378(16) 0.0403(16) 0.0299(14) 0.0128(13) 0.0042(12) 0.0157(13) C7 0.0477(18) 0.0425(18) 0.0345(15) 0.0070(14) 0.0114(14) 0.0175(15) C8 0.0488(19) 0.0421(18) 0.0500(19) 0.0115(15) 0.0185(16) 0.0255(15) C9 0.0351(15) 0.0432(17) 0.0457(17) 0.0153(14) 0.0104(13) 0.0229(14) C10 0.0248(13) 0.0341(15) 0.0329(14) 0.0140(12) 0.0078(11) 0.0126(11) C11 0.0385(16) 0.0362(16) 0.0325(14) 0.0072(12) 0.0130(12) 0.0210(13) C12 0.0420(16) 0.0393(16) 0.0282(14) 0.0057(12) 0.0095(12) 0.0222(13) C13 0.0326(14) 0.0255(13) 0.0304(14) 0.0060(11) 0.0143(11) 0.0112(11) C14 0.0429(17) 0.0386(16) 0.0364(15) 0.0051(13) 0.0113(13) 0.0269(14) C15 0.0425(17) 0.0410(17) 0.0306(14) 0.0024(13) 0.0069(13) 0.0231(14) N1 0.0306(12) 0.0398(13) 0.0271(11) 0.0140(10) 0.0038(9) 0.0192(10) N2 0.0343(12) 0.0291(12) 0.0325(12) 0.0046(10) 0.0128(10) 0.0157(10) O1 0.0297(11) 0.0411(12) 0.0397(11) 0.0111(9) -0.0002(9) 0.0165(9) O2 0.0415(14) 0.0738(19) 0.0865(19) 0.0542(17) -0.0032(13) 0.0142(13) O3 0.0376(11) 0.0487(13) 0.0343(10) 0.0121(9) 0.0083(9) 0.0278(10) O4 0.0388(11) 0.0432(12) 0.0324(10) 0.0133(9) 0.0080(9) 0.0211(9) Cd1 0.02653(16) 0.03082(17) 0.02256(16) 0.00164(11) 0.00386(11) 0.01638(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.232(4) . ? C1 O1 1.245(4) . ? C1 C2 1.517(3) . ? C2 C3 1.345(4) . ? C2 C10 1.444(4) . ? C3 C4 1.439(4) . ? C3 H3 0.9300 . ? C4 O3 1.250(3) . ? C4 N1 1.360(4) . ? C5 N1 1.380(4) . ? C5 C6 1.394(4) . ? C5 C10 1.401(4) . ? C6 C7 1.366(4) . ? C6 H6 0.9300 . ? C7 C8 1.400(5) . ? C7 H7 0.9300 . ? C8 C9 1.367(4) . ? C8 H8 0.9300 . ? C9 C10 1.400(4) . ? C9 H9 0.9300 . ? C11 N2 1.332(4) . ? C11 C12 1.375(4) . ? C11 H11 0.9300 . ? C12 C13 1.388(4) . ? C12 H12 0.9300 . ? C13 C14 1.384(4) . ? C13 C13 1.482(5) 2_788 ? C14 C15 1.383(4) . ? C14 H14 0.9300 . ? C15 N2 1.332(4) . ? C15 H15 0.9300 . ? N1 H1 0.8600 . ? N2 Cd1 2.305(2) . ? O1 Cd1 2.2820(19) . ? O4 Cd1 2.354(2) . ? O4 H4A 0.8732 . ? O4 H4B 0.8575 . ? Cd1 O1 2.2820(19) 2_777 ? Cd1 N2 2.305(2) 2_777 ? Cd1 O4 2.354(2) 2_777 ? 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 C1 O1 127.0(3) . . ? O2 C1 C2 116.9(3) . . ? O1 C1 C2 116.0(3) . . ? C3 C2 C10 120.6(2) . . ? C3 C2 C1 120.2(2) . . ? C10 C2 C1 119.2(2) . . ? C2 C3 C4 121.8(3) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? O3 C4 N1 120.1(2) . . ? O3 C4 C3 124.0(3) . . ? N1 C4 C3 115.8(2) . . ? N1 C5 C6 120.6(2) . . ? N1 C5 C10 118.7(2) . . ? C6 C5 C10 120.7(3) . . ? C7 C6 C5 119.6(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.7(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.7(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.1(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C5 118.2(3) . . ? C9 C10 C2 123.9(2) . . ? C5 C10 C2 117.9(2) . . ? N2 C11 C12 123.6(3) . . ? N2 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 116.5(2) . . ? C14 C13 C13 122.0(3) . 2_788 ? C12 C13 C13 121.5(3) . 2_788 ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? N2 C15 C14 122.8(3) . . ? N2 C15 H15 118.6 . . ? C14 C15 H15 118.6 . . ? C4 N1 C5 125.1(2) . . ? C4 N1 H1 117.5 . . ? C5 N1 H1 117.5 . . ? C11 N2 C15 117.1(2) . . ? C11 N2 Cd1 120.87(18) . . ? C15 N2 Cd1 121.89(19) . . ? C1 O1 Cd1 127.41(19) . . ? Cd1 O4 H4A 99.7 . . ? Cd1 O4 H4B 109.0 . . ? H4A O4 H4B 109.3 . . ? O1 Cd1 O1 180.000(1) . 2_777 ? O1 Cd1 N2 90.00(8) . 2_777 ? O1 Cd1 N2 90.00(8) 2_777 2_777 ? O1 Cd1 N2 90.00(8) . . ? O1 Cd1 N2 90.00(8) 2_777 . ? N2 Cd1 N2 180.000(1) 2_777 . ? O1 Cd1 O4 90.94(7) . 2_777 ? O1 Cd1 O4 89.06(7) 2_777 2_777 ? N2 Cd1 O4 94.00(8) 2_777 2_777 ? N2 Cd1 O4 86.00(8) . 2_777 ? O1 Cd1 O4 89.06(7) . . ? O1 Cd1 O4 90.94(7) 2_777 . ? N2 Cd1 O4 86.00(8) 2_777 . ? N2 Cd1 O4 94.00(8) . . ? O4 Cd1 O4 180.0 2_777 . ? 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 C1 C2 C3 105.7(4) . . . . ? O1 C1 C2 C3 -76.1(4) . . . . ? O2 C1 C2 C10 -72.2(4) . . . . ? O1 C1 C2 C10 106.0(3) . . . . ? C10 C2 C3 C4 3.3(4) . . . . ? C1 C2 C3 C4 -174.7(3) . . . . ? C2 C3 C4 O3 174.9(3) . . . . ? C2 C3 C4 N1 -3.8(4) . . . . ? N1 C5 C6 C7 -178.6(3) . . . . ? C10 C5 C6 C7 0.3(5) . . . . ? C5 C6 C7 C8 0.0(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? C8 C9 C10 C5 1.0(5) . . . . ? C8 C9 C10 C2 -179.0(3) . . . . ? N1 C5 C10 C9 178.1(3) . . . . ? C6 C5 C10 C9 -0.8(4) . . . . ? N1 C5 C10 C2 -1.9(4) . . . . ? C6 C5 C10 C2 179.2(3) . . . . ? C3 C2 C10 C9 179.7(3) . . . . ? C1 C2 C10 C9 -2.4(4) . . . . ? C3 C2 C10 C5 -0.3(4) . . . . ? C1 C2 C10 C5 177.6(3) . . . . ? N2 C11 C12 C13 0.6(5) . . . . ? C11 C12 C13 C14 0.8(4) . . . . ? C11 C12 C13 C13 -179.9(3) . . . 2_788 ? C12 C13 C14 C15 -1.1(5) . . . . ? C13 C13 C14 C15 179.6(3) 2_788 . . . ? C13 C14 C15 N2 0.2(5) . . . . ? O3 C4 N1 C5 -177.3(3) . . . . ? C3 C4 N1 C5 1.5(4) . . . . ? C6 C5 N1 C4 -179.8(3) . . . . ? C10 C5 N1 C4 1.3(4) . . . . ? C12 C11 N2 C15 -1.6(5) . . . . ? C12 C11 N2 Cd1 174.1(2) . . . . ? C14 C15 N2 C11 1.2(5) . . . . ? C14 C15 N2 Cd1 -174.5(2) . . . . ? O2 C1 O1 Cd1 -0.2(5) . . . . ? C2 C1 O1 Cd1 -178.12(17) . . . . ? C1 O1 Cd1 O1 35(100) . . . 2_777 ? C1 O1 Cd1 N2 78.3(2) . . . 2_777 ? C1 O1 Cd1 N2 -101.7(2) . . . . ? C1 O1 Cd1 O4 172.3(2) . . . 2_777 ? C1 O1 Cd1 O4 -7.7(2) . . . . ? C11 N2 Cd1 O1 168.5(2) . . . . ? C15 N2 Cd1 O1 -16.0(2) . . . . ? C11 N2 Cd1 O1 -11.5(2) . . . 2_777 ? C15 N2 Cd1 O1 164.0(2) . . . 2_777 ? C11 N2 Cd1 N2 -41(100) . . . 2_777 ? C15 N2 Cd1 N2 134(100) . . . 2_777 ? C11 N2 Cd1 O4 -100.6(2) . . . 2_777 ? C15 N2 Cd1 O4 74.9(2) . . . 2_777 ? C11 N2 Cd1 O4 79.4(2) . . . . ? C15 N2 Cd1 O4 -105.1(2) . . . . ? 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 O4 H4B O3 0.86 1.87 2.722(3) 174.6 2_677 N1 H1 O3 0.86 2.15 2.911(3) 147.8 2_576 O4 H4A O1 0.87 2.85 3.252(3) 109.6 . O4 H4A O2 0.87 1.85 2.692(3) 160.5 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.597 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.079 # Attachment '- 5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 853363' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 N4 O8 Zn' _chemical_formula_weight 661.95 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 9.160(3) _cell_length_b 13.013(4) _cell_length_c 13.708(4) _cell_angle_alpha 109.512(4) _cell_angle_beta 103.074(4) _cell_angle_gamma 91.406(4) _cell_volume 1491.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2090 _cell_measurement_theta_min 2.462 _cell_measurement_theta_max 23.195 _exptl_crystal_description block _exptl_crystal_colour courlorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8363 _exptl_absorpt_correction_T_max 0.9327 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 7839 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.49 _reflns_number_total 5438 _reflns_number_gt 4400 _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^)+(0.0730P)^2^+0.6503P] 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 5438 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4306(5) 0.3565(3) 0.2592(3) 0.0401(9) Uani 1 1 d . . . C2 C 0.3928(6) 0.4323(3) 0.2093(4) 0.0585(13) Uani 1 1 d . . . H2 H 0.3897 0.5050 0.2502 0.070 Uiso 1 1 calc R . . C3 C 0.3600(6) 0.4011(4) 0.0998(4) 0.0592(13) Uani 1 1 d . . . H3 H 0.3343 0.4522 0.0667 0.071 Uiso 1 1 calc R . . C4 C 0.3656(5) 0.2933(3) 0.0395(3) 0.0467(10) Uani 1 1 d . . . H4 H 0.3440 0.2717 -0.0346 0.056 Uiso 1 1 calc R . . C5 C 0.4028(4) 0.2179(3) 0.0882(3) 0.0338(8) Uani 1 1 d . . . H5 H 0.4078 0.1458 0.0464 0.041 Uiso 1 1 calc R . . C6 C 0.4332(4) 0.2463(3) 0.1988(3) 0.0312(8) Uani 1 1 d . . . C7 C 0.4739(4) 0.1633(3) 0.2542(3) 0.0276(8) Uani 1 1 d . . . C8 C 0.4595(4) 0.2089(3) 0.3707(3) 0.0313(8) Uani 1 1 d . . . H8 H 0.5195 0.1703 0.4133 0.038 Uiso 1 1 calc R . . C9 C 0.4834(5) 0.3307(3) 0.4313(3) 0.0405(9) Uani 1 1 d . . . C10 C 0.2935(4) 0.1578(3) 0.3308(3) 0.0319(8) Uani 1 1 d . . . H10 H 0.2298 0.2091 0.3080 0.038 Uiso 1 1 calc R . . C11 C 0.2266(5) 0.1177(3) 0.4027(3) 0.0403(9) Uani 1 1 d . . . C12 C 0.3330(4) -0.0542(3) 0.3349(3) 0.0365(9) Uani 1 1 d . . . C13 C 0.3659(5) -0.1510(4) 0.3534(4) 0.0521(12) Uani 1 1 d . . . H13 H 0.3356 -0.1661 0.4080 0.063 Uiso 1 1 calc R . . C14 C 0.4414(6) -0.2232(4) 0.2927(4) 0.0546(12) Uani 1 1 d . . . H14 H 0.4648 -0.2871 0.3063 0.065 Uiso 1 1 calc R . . C15 C 0.4837(5) -0.2018(3) 0.2106(4) 0.0509(11) Uani 1 1 d . . . H15 H 0.5339 -0.2521 0.1678 0.061 Uiso 1 1 calc R . . C16 C 0.4519(4) -0.1058(3) 0.1913(3) 0.0362(9) Uani 1 1 d . . . H16 H 0.4810 -0.0923 0.1355 0.043 Uiso 1 1 calc R . . C17 C 0.3771(4) -0.0293(3) 0.2541(3) 0.0290(8) Uani 1 1 d . . . C18 C 0.3336(4) 0.0746(3) 0.2325(3) 0.0285(8) Uani 1 1 d . . . C19 C 0.2130(4) 0.0478(3) 0.1261(3) 0.0280(8) Uani 1 1 d . . . C20 C 0.6268(4) 0.1262(3) 0.2390(3) 0.0315(8) Uani 1 1 d . . . C21 C 0.7741(5) 0.2678(3) 0.0804(4) 0.0496(11) Uani 1 1 d . . . H21 H 0.7132 0.2177 0.0178 0.060 Uiso 1 1 calc R . . C22 C 0.7687(6) 0.3776(4) 0.0975(4) 0.0604(13) Uani 1 1 d . . . H22 H 0.7064 0.4002 0.0466 0.072 Uiso 1 1 calc R . . C23 C 0.8549(6) 0.4537(4) 0.1892(5) 0.0625(14) Uani 1 1 d . . . C24 C 0.9459(7) 0.4141(4) 0.2617(5) 0.089(2) Uani 1 1 d . . . H24 H 1.0073 0.4624 0.3251 0.107 Uiso 1 1 calc R . . C25 C 0.9440(6) 0.3028(3) 0.2385(4) 0.0649(15) Uani 1 1 d . . . H25 H 1.0036 0.2776 0.2884 0.078 Uiso 1 1 calc R . . C26 C 0.8470(7) 0.5752(4) 0.2109(6) 0.089(2) Uani 1 1 d . . . H26A H 0.7782 0.5843 0.1500 0.107 Uiso 1 1 calc R . . H26B H 0.8049 0.6051 0.2722 0.107 Uiso 1 1 calc R . . C27 C 0.9949(5) 0.6403(4) 0.2320(4) 0.0595(13) Uani 1 1 d . . . H27A H 1.0552 0.5976 0.1866 0.071 Uiso 1 1 calc R . . H27B H 1.0496 0.6572 0.3058 0.071 Uiso 1 1 calc R . . C28 C 0.9694(5) 0.7453(3) 0.2100(4) 0.0445(10) Uani 1 1 d . . . C29 C 1.0084(5) 0.7624(3) 0.1258(4) 0.0495(11) Uani 1 1 d . . . H29 H 1.0607 0.7117 0.0852 0.059 Uiso 1 1 calc R . . C30 C 0.9715(5) 0.8534(3) 0.1000(4) 0.0431(10) Uani 1 1 d . . . H30 H 0.9983 0.8623 0.0416 0.052 Uiso 1 1 calc R . . C31 C 0.8609(5) 0.9146(3) 0.2393(3) 0.0392(9) Uani 1 1 d . . . H31 H 0.8108 0.9673 0.2798 0.047 Uiso 1 1 calc R . . C32 C 0.8937(5) 0.8241(3) 0.2676(3) 0.0461(10) Uani 1 1 d . . . H32 H 0.8646 0.8161 0.3257 0.055 Uiso 1 1 calc R . . N1 N 0.4641(4) 0.3940(3) 0.3710(3) 0.0483(9) Uani 1 1 d . . . H1 H 0.4729 0.4637 0.4037 0.058 Uiso 1 1 calc R . . N2 N 0.2506(4) 0.0158(3) 0.3998(3) 0.0433(8) Uani 1 1 d . . . H2A H 0.2129 -0.0088 0.4407 0.052 Uiso 1 1 calc R . . N3 N 0.8616(3) 0.2296(2) 0.1485(3) 0.0351(7) Uani 1 1 d . . . N4 N 0.8980(3) 0.9297(2) 0.1564(3) 0.0333(7) Uani 1 1 d . . . O1 O 0.7362(3) 0.1606(2) 0.3186(2) 0.0481(7) Uani 1 1 d . . . O2 O 0.6343(3) 0.0691(2) 0.1465(2) 0.0355(6) Uani 1 1 d . . . O3 O 0.2480(3) -0.01509(19) 0.04437(19) 0.0341(6) Uani 1 1 d . . . O4 O 0.0923(3) 0.0888(2) 0.1281(2) 0.0386(6) Uani 1 1 d . . . O5 O 0.5123(4) 0.3684(2) 0.5289(2) 0.0596(9) Uani 1 1 d . . . O6 O 0.1552(4) 0.1758(3) 0.4622(3) 0.0616(9) Uani 1 1 d . . . O7 O 0.1370(8) 0.6246(5) 0.5110(6) 0.071(2) Uani 0.50 1 d P . . H7A H 0.0418 0.6249 0.4978 0.107 Uiso 0.50 1 d PR . . H7B H 0.1853 0.5686 0.4986 0.107 Uiso 0.50 1 d PR . . O8 O 0.8757(4) 0.0971(3) 0.4860(3) 0.0723(11) Uani 1 1 d . . . H8A H 0.8225 0.1183 0.4384 0.108 Uiso 1 1 d R . . H8B H 0.9689 0.1041 0.4878 0.108 Uiso 1 1 d R . . O9 O 0.1691(9) 0.4168(6) 0.5234(8) 0.103(3) Uani 0.50 1 d P . . H9B H 0.2274 0.4192 0.5822 0.154 Uiso 0.50 1 d PR . . H9A H 0.0845 0.3785 0.5055 0.154 Uiso 0.50 1 d PR . . Zn1 Zn 0.84178(5) 0.06205(3) 0.11214(3) 0.02793(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.058(3) 0.0270(19) 0.035(2) 0.0096(17) 0.0125(19) 0.0061(18) C2 0.098(4) 0.029(2) 0.051(3) 0.016(2) 0.019(3) 0.015(2) C3 0.089(4) 0.048(3) 0.052(3) 0.034(2) 0.014(3) 0.012(2) C4 0.060(3) 0.048(3) 0.036(2) 0.021(2) 0.010(2) 0.003(2) C5 0.036(2) 0.036(2) 0.031(2) 0.0133(16) 0.0095(17) -0.0003(16) C6 0.036(2) 0.0274(19) 0.032(2) 0.0118(16) 0.0106(16) 0.0018(15) C7 0.034(2) 0.0207(17) 0.0247(18) 0.0051(14) 0.0060(15) -0.0020(14) C8 0.038(2) 0.0280(19) 0.0269(19) 0.0086(15) 0.0088(16) 0.0002(15) C9 0.057(3) 0.031(2) 0.030(2) 0.0057(17) 0.0116(19) -0.0012(18) C10 0.041(2) 0.0287(19) 0.0274(19) 0.0078(15) 0.0148(17) 0.0042(16) C11 0.049(2) 0.036(2) 0.039(2) 0.0099(18) 0.021(2) 0.0015(18) C12 0.043(2) 0.035(2) 0.033(2) 0.0152(17) 0.0080(18) -0.0009(17) C13 0.070(3) 0.051(3) 0.051(3) 0.035(2) 0.021(2) 0.007(2) C14 0.071(3) 0.037(2) 0.070(3) 0.032(2) 0.024(3) 0.015(2) C15 0.063(3) 0.036(2) 0.063(3) 0.021(2) 0.028(2) 0.015(2) C16 0.042(2) 0.030(2) 0.039(2) 0.0123(17) 0.0148(18) 0.0024(16) C17 0.033(2) 0.0250(18) 0.030(2) 0.0111(15) 0.0082(16) -0.0003(14) C18 0.034(2) 0.0263(18) 0.0290(19) 0.0108(15) 0.0134(16) 0.0020(15) C19 0.031(2) 0.0211(17) 0.032(2) 0.0105(15) 0.0075(16) -0.0037(14) C20 0.033(2) 0.0266(18) 0.039(2) 0.0180(17) 0.0079(18) 0.0024(15) C21 0.058(3) 0.035(2) 0.054(3) 0.018(2) 0.006(2) 0.002(2) C22 0.070(3) 0.041(3) 0.076(4) 0.032(3) 0.011(3) 0.010(2) C23 0.058(3) 0.029(2) 0.101(4) 0.027(3) 0.015(3) 0.007(2) C24 0.090(4) 0.030(3) 0.104(5) 0.004(3) -0.030(4) 0.000(3) C25 0.071(3) 0.030(2) 0.070(3) 0.009(2) -0.016(3) 0.010(2) C26 0.080(4) 0.030(3) 0.150(6) 0.034(3) 0.012(4) 0.004(3) C27 0.054(3) 0.042(3) 0.086(4) 0.037(3) 0.002(3) 0.005(2) C28 0.040(2) 0.029(2) 0.062(3) 0.023(2) -0.002(2) -0.0008(17) C29 0.050(3) 0.032(2) 0.077(3) 0.024(2) 0.027(2) 0.0131(19) C30 0.044(2) 0.035(2) 0.060(3) 0.022(2) 0.022(2) 0.0075(18) C31 0.052(3) 0.028(2) 0.037(2) 0.0122(17) 0.0093(19) 0.0048(17) C32 0.062(3) 0.036(2) 0.041(2) 0.0199(19) 0.005(2) 0.001(2) N1 0.086(3) 0.0220(16) 0.0324(19) 0.0046(14) 0.0137(18) -0.0017(17) N2 0.059(2) 0.043(2) 0.038(2) 0.0181(16) 0.0268(17) 0.0016(16) N3 0.0350(18) 0.0239(16) 0.048(2) 0.0126(14) 0.0128(15) 0.0044(13) N4 0.0361(18) 0.0236(15) 0.0430(19) 0.0158(14) 0.0091(15) 0.0035(13) O1 0.0358(16) 0.0585(19) 0.0449(18) 0.0185(14) -0.0002(14) 0.0049(13) O2 0.0376(15) 0.0300(14) 0.0396(16) 0.0082(12) 0.0168(12) 0.0055(11) O3 0.0403(15) 0.0304(14) 0.0287(14) 0.0071(11) 0.0077(12) 0.0030(11) O4 0.0346(15) 0.0312(14) 0.0457(17) 0.0093(12) 0.0077(13) 0.0053(11) O5 0.105(3) 0.0358(16) 0.0302(17) 0.0040(13) 0.0149(17) -0.0085(16) O6 0.081(2) 0.0523(19) 0.067(2) 0.0179(17) 0.053(2) 0.0140(17) O7 0.068(5) 0.048(4) 0.070(5) -0.004(3) 0.004(4) -0.011(3) O8 0.060(2) 0.116(3) 0.060(2) 0.057(2) 0.0133(18) -0.004(2) O9 0.080(6) 0.042(4) 0.176(10) 0.022(5) 0.034(6) 0.030(4) Zn1 0.0356(3) 0.0198(2) 0.0299(2) 0.00980(17) 0.00904(18) 0.00410(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.386(5) . ? C1 C6 1.399(5) . ? C1 N1 1.400(5) . ? C2 C3 1.375(6) . ? C2 H2 0.9300 . ? C3 C4 1.379(6) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4 0.9300 . ? C5 C6 1.394(5) . ? C5 H5 0.9300 . ? C6 C7 1.524(5) . ? C7 C20 1.528(5) . ? C7 C8 1.545(5) . ? C7 C18 1.612(5) . ? C8 C9 1.507(5) . ? C8 C10 1.545(5) . ? C8 H8 0.9800 . ? C9 O5 1.223(5) . ? C9 N1 1.338(5) . ? C10 C11 1.490(5) . ? C10 C18 1.546(5) . ? C10 H10 0.9800 . ? C11 O6 1.233(4) . ? C11 N2 1.338(5) . ? C12 C17 1.389(5) . ? C12 C13 1.393(5) . ? C12 N2 1.410(5) . ? C13 C14 1.351(6) . ? C13 H13 0.9300 . ? C14 C15 1.377(6) . ? C14 H14 0.9300 . ? C15 C16 1.386(5) . ? C15 H15 0.9300 . ? C16 C17 1.389(5) . ? C16 H16 0.9300 . ? C17 C18 1.522(5) . ? C18 C19 1.544(5) . ? C19 O4 1.240(4) . ? C19 O3 1.261(4) . ? C20 O1 1.246(5) . ? C20 O2 1.255(4) . ? C21 N3 1.323(5) . ? C21 C22 1.372(6) . ? C21 H21 0.9300 . ? C22 C23 1.366(7) . ? C22 H22 0.9300 . ? C23 C24 1.392(7) . ? C23 C26 1.514(6) . ? C24 C25 1.373(6) . ? C24 H24 0.9300 . ? C25 N3 1.326(5) . ? C25 H25 0.9300 . ? C26 C27 1.498(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.506(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.366(6) . ? C28 C32 1.378(6) . ? C29 C30 1.373(5) . ? C29 H29 0.9300 . ? C30 N4 1.339(5) . ? C30 H30 0.9300 . ? C31 N4 1.328(5) . ? C31 C32 1.379(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? N1 H1 0.8600 . ? N2 H2A 0.8600 . ? N3 Zn1 2.062(3) . ? N4 Zn1 2.049(3) 1_565 ? O2 Zn1 2.056(2) . ? O3 Zn1 1.988(3) 2_655 ? O4 Zn1 2.263(3) 1_455 ? O7 H7A 0.8500 . ? O7 H7B 0.8500 . ? O8 H8A 0.8500 . ? O8 H8B 0.8500 . ? O9 H9B 0.8500 . ? O9 H9A 0.8500 . ? Zn1 O3 1.988(3) 2_655 ? Zn1 N4 2.049(3) 1_545 ? Zn1 O4 2.263(3) 1_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.5(4) . . ? C2 C1 N1 117.7(3) . . ? C6 C1 N1 121.8(3) . . ? C3 C2 C1 120.7(4) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.7(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 117.4(3) . . ? C5 C6 C7 122.3(3) . . ? C1 C6 C7 120.2(3) . . ? C6 C7 C20 108.8(3) . . ? C6 C7 C8 110.5(3) . . ? C20 C7 C8 116.1(3) . . ? C6 C7 C18 112.7(3) . . ? C20 C7 C18 120.6(3) . . ? C8 C7 C18 86.4(2) . . ? C9 C8 C10 115.2(3) . . ? C9 C8 C7 120.4(3) . . ? C10 C8 C7 88.8(3) . . ? C9 C8 H8 110.2 . . ? C10 C8 H8 110.2 . . ? C7 C8 H8 110.2 . . ? O5 C9 N1 122.6(4) . . ? O5 C9 C8 121.9(3) . . ? N1 C9 C8 115.4(3) . . ? C11 C10 C8 118.5(3) . . ? C11 C10 C18 119.9(3) . . ? C8 C10 C18 88.8(3) . . ? C11 C10 H10 109.4 . . ? C8 C10 H10 109.4 . . ? C18 C10 H10 109.4 . . ? O6 C11 N2 122.2(3) . . ? O6 C11 C10 121.7(4) . . ? N2 C11 C10 116.0(3) . . ? C17 C12 C13 121.0(4) . . ? C17 C12 N2 121.6(3) . . ? C13 C12 N2 117.3(3) . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.6(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.5(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 120.8(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C12 117.4(3) . . ? C16 C17 C18 122.5(3) . . ? C12 C17 C18 119.9(3) . . ? C17 C18 C19 111.3(3) . . ? C17 C18 C10 110.6(3) . . ? C19 C18 C10 115.1(3) . . ? C17 C18 C7 114.6(3) . . ? C19 C18 C7 116.7(3) . . ? C10 C18 C7 86.3(2) . . ? O4 C19 O3 126.1(3) . . ? O4 C19 C18 118.2(3) . . ? O3 C19 C18 115.6(3) . . ? O1 C20 O2 125.1(3) . . ? O1 C20 C7 117.0(3) . . ? O2 C20 C7 117.7(3) . . ? N3 C21 C22 123.3(4) . . ? N3 C21 H21 118.3 . . ? C22 C21 H21 118.3 . . ? C23 C22 C21 120.1(5) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 116.8(4) . . ? C22 C23 C26 120.8(5) . . ? C24 C23 C26 122.3(5) . . ? C25 C24 C23 119.3(5) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? N3 C25 C24 123.3(5) . . ? N3 C25 H25 118.4 . . ? C24 C25 H25 118.4 . . ? C27 C26 C23 114.9(4) . . ? C27 C26 H26A 108.5 . . ? C23 C26 H26A 108.5 . . ? C27 C26 H26B 108.5 . . ? C23 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? C26 C27 C28 110.1(4) . . ? C26 C27 H27A 109.6 . . ? C28 C27 H27A 109.6 . . ? C26 C27 H27B 109.6 . . ? C28 C27 H27B 109.6 . . ? H27A C27 H27B 108.2 . . ? C29 C28 C32 116.7(4) . . ? C29 C28 C27 121.4(4) . . ? C32 C28 C27 121.7(4) . . ? C28 C29 C30 121.0(4) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? N4 C30 C29 122.0(4) . . ? N4 C30 H30 119.0 . . ? C29 C30 H30 119.0 . . ? N4 C31 C32 122.6(4) . . ? N4 C31 H31 118.7 . . ? C32 C31 H31 118.7 . . ? C28 C32 C31 120.1(4) . . ? C28 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C9 N1 C1 125.7(3) . . ? C9 N1 H1 117.2 . . ? C1 N1 H1 117.2 . . ? C11 N2 C12 125.1(3) . . ? C11 N2 H2A 117.5 . . ? C12 N2 H2A 117.5 . . ? C21 N3 C25 117.1(4) . . ? C21 N3 Zn1 117.0(3) . . ? C25 N3 Zn1 125.6(3) . . ? C31 N4 C30 117.6(3) . . ? C31 N4 Zn1 122.1(3) . 1_565 ? C30 N4 Zn1 120.3(3) . 1_565 ? C20 O2 Zn1 118.4(2) . . ? C19 O3 Zn1 134.6(2) . 2_655 ? C19 O4 Zn1 147.5(2) . 1_455 ? H7A O7 H7B 126.8 . . ? H8A O8 H8B 111.6 . . ? H9B O9 H9A 115.6 . . ? O3 Zn1 N4 110.80(11) 2_655 1_545 ? O3 Zn1 O2 92.87(10) 2_655 . ? N4 Zn1 O2 96.46(11) 1_545 . ? O3 Zn1 N3 99.24(12) 2_655 . ? N4 Zn1 N3 148.92(13) 1_545 . ? O2 Zn1 N3 89.63(11) . . ? O3 Zn1 O4 103.87(10) 2_655 1_655 ? N4 Zn1 O4 83.51(11) 1_545 1_655 ? O2 Zn1 O4 162.15(10) . 1_655 ? N3 Zn1 O4 81.70(10) . 1_655 ? 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 C6 C1 C2 C3 -1.2(7) . . . . ? N1 C1 C2 C3 179.4(5) . . . . ? C1 C2 C3 C4 -0.3(8) . . . . ? C2 C3 C4 C5 0.3(7) . . . . ? C3 C4 C5 C6 1.2(7) . . . . ? C4 C5 C6 C1 -2.6(6) . . . . ? C4 C5 C6 C7 179.7(3) . . . . ? C2 C1 C6 C5 2.6(6) . . . . ? N1 C1 C6 C5 -178.1(4) . . . . ? C2 C1 C6 C7 -179.6(4) . . . . ? N1 C1 C6 C7 -0.3(6) . . . . ? C5 C6 C7 C20 66.5(4) . . . . ? C1 C6 C7 C20 -111.1(4) . . . . ? C5 C6 C7 C8 -164.8(3) . . . . ? C1 C6 C7 C8 17.6(5) . . . . ? C5 C6 C7 C18 -70.0(4) . . . . ? C1 C6 C7 C18 112.4(4) . . . . ? C6 C7 C8 C9 -28.8(5) . . . . ? C20 C7 C8 C9 95.7(4) . . . . ? C18 C7 C8 C9 -141.8(3) . . . . ? C6 C7 C8 C10 89.9(3) . . . . ? C20 C7 C8 C10 -145.5(3) . . . . ? C18 C7 C8 C10 -23.0(2) . . . . ? C10 C8 C9 O5 95.3(5) . . . . ? C7 C8 C9 O5 -160.3(4) . . . . ? C10 C8 C9 N1 -81.9(4) . . . . ? C7 C8 C9 N1 22.5(5) . . . . ? C9 C8 C10 C11 -89.0(4) . . . . ? C7 C8 C10 C11 147.7(3) . . . . ? C9 C8 C10 C18 147.3(3) . . . . ? C7 C8 C10 C18 24.0(2) . . . . ? C8 C10 C11 O6 94.3(5) . . . . ? C18 C10 C11 O6 -159.3(4) . . . . ? C8 C10 C11 N2 -84.8(4) . . . . ? C18 C10 C11 N2 21.6(6) . . . . ? C17 C12 C13 C14 -0.2(7) . . . . ? N2 C12 C13 C14 178.5(4) . . . . ? C12 C13 C14 C15 -1.2(8) . . . . ? C13 C14 C15 C16 1.3(8) . . . . ? C14 C15 C16 C17 0.0(7) . . . . ? C15 C16 C17 C12 -1.4(6) . . . . ? C15 C16 C17 C18 -177.1(4) . . . . ? C13 C12 C17 C16 1.5(6) . . . . ? N2 C12 C17 C16 -177.2(4) . . . . ? C13 C12 C17 C18 177.3(4) . . . . ? N2 C12 C17 C18 -1.3(6) . . . . ? C16 C17 C18 C19 66.5(4) . . . . ? C12 C17 C18 C19 -109.1(4) . . . . ? C16 C17 C18 C10 -164.2(3) . . . . ? C12 C17 C18 C10 20.2(5) . . . . ? C16 C17 C18 C7 -68.6(4) . . . . ? C12 C17 C18 C7 115.8(4) . . . . ? C11 C10 C18 C17 -30.6(5) . . . . ? C8 C10 C18 C17 92.0(3) . . . . ? C11 C10 C18 C19 96.7(4) . . . . ? C8 C10 C18 C19 -140.8(3) . . . . ? C11 C10 C18 C7 -145.5(4) . . . . ? C8 C10 C18 C7 -23.0(2) . . . . ? C6 C7 C18 C17 161.2(3) . . . . ? C20 C7 C18 C17 30.3(4) . . . . ? C8 C7 C18 C17 -88.0(3) . . . . ? C6 C7 C18 C19 28.5(4) . . . . ? C20 C7 C18 C19 -102.3(4) . . . . ? C8 C7 C18 C19 139.3(3) . . . . ? C6 C7 C18 C10 -87.7(3) . . . . ? C20 C7 C18 C10 141.4(3) . . . . ? C8 C7 C18 C10 23.0(3) . . . . ? C17 C18 C19 O4 122.8(3) . . . . ? C10 C18 C19 O4 -4.1(4) . . . . ? C7 C18 C19 O4 -103.1(3) . . . . ? C17 C18 C19 O3 -57.0(4) . . . . ? C10 C18 C19 O3 176.2(3) . . . . ? C7 C18 C19 O3 77.2(4) . . . . ? C6 C7 C20 O1 107.4(4) . . . . ? C8 C7 C20 O1 -18.0(4) . . . . ? C18 C7 C20 O1 -120.1(4) . . . . ? C6 C7 C20 O2 -68.6(4) . . . . ? C8 C7 C20 O2 165.9(3) . . . . ? C18 C7 C20 O2 63.9(4) . . . . ? N3 C21 C22 C23 -1.0(8) . . . . ? C21 C22 C23 C24 0.2(8) . . . . ? C21 C22 C23 C26 -178.2(5) . . . . ? C22 C23 C24 C25 -0.5(9) . . . . ? C26 C23 C24 C25 177.9(6) . . . . ? C23 C24 C25 N3 1.5(10) . . . . ? C22 C23 C26 C27 -124.1(6) . . . . ? C24 C23 C26 C27 57.6(9) . . . . ? C23 C26 C27 C28 158.0(5) . . . . ? C26 C27 C28 C29 -111.3(6) . . . . ? C26 C27 C28 C32 62.8(6) . . . . ? C32 C28 C29 C30 -0.8(7) . . . . ? C27 C28 C29 C30 173.6(4) . . . . ? C28 C29 C30 N4 0.9(7) . . . . ? C29 C28 C32 C31 0.0(6) . . . . ? C27 C28 C32 C31 -174.3(4) . . . . ? N4 C31 C32 C28 0.8(7) . . . . ? O5 C9 N1 C1 -179.9(4) . . . . ? C8 C9 N1 C1 -2.8(6) . . . . ? C2 C1 N1 C9 170.8(4) . . . . ? C6 C1 N1 C9 -8.5(7) . . . . ? O6 C11 N2 C12 -179.1(4) . . . . ? C10 C11 N2 C12 0.0(6) . . . . ? C17 C12 N2 C11 -10.6(6) . . . . ? C13 C12 N2 C11 170.7(4) . . . . ? C22 C21 N3 C25 1.9(7) . . . . ? C22 C21 N3 Zn1 176.0(4) . . . . ? C24 C25 N3 C21 -2.2(8) . . . . ? C24 C25 N3 Zn1 -175.7(5) . . . . ? C32 C31 N4 C30 -0.7(6) . . . . ? C32 C31 N4 Zn1 177.8(3) . . . 1_565 ? C29 C30 N4 C31 -0.1(6) . . . . ? C29 C30 N4 Zn1 -178.6(3) . . . 1_565 ? O1 C20 O2 Zn1 -16.2(5) . . . . ? C7 C20 O2 Zn1 159.5(2) . . . . ? O4 C19 O3 Zn1 10.4(5) . . . 2_655 ? C18 C19 O3 Zn1 -169.9(2) . . . 2_655 ? O3 C19 O4 Zn1 70.4(6) . . . 1_455 ? C18 C19 O4 Zn1 -109.3(4) . . . 1_455 ? C20 O2 Zn1 O3 -159.1(2) . . . 2_655 ? C20 O2 Zn1 N4 89.6(3) . . . 1_545 ? C20 O2 Zn1 N3 -59.9(3) . . . . ? C20 O2 Zn1 O4 0.7(5) . . . 1_655 ? C21 N3 Zn1 O3 21.6(3) . . . 2_655 ? C25 N3 Zn1 O3 -164.9(4) . . . 2_655 ? C21 N3 Zn1 N4 -173.2(3) . . . 1_545 ? C25 N3 Zn1 N4 0.3(5) . . . 1_545 ? C21 N3 Zn1 O2 -71.2(3) . . . . ? C25 N3 Zn1 O2 102.3(4) . . . . ? C21 N3 Zn1 O4 124.4(3) . . . 1_655 ? C25 N3 Zn1 O4 -62.1(4) . . . 1_655 ? 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 O8 H8B O6 0.85 2.08 2.860(4) 152.7 1_655 N1 H1 O5 0.86 2.06 2.914(4) 175.8 2_666 N2 H2A O8 0.86 2.02 2.868(4) 168.2 2_656 O8 H8A O1 0.85 1.91 2.752(4) 168.6 . O7 H7B O9 0.85 2.12 2.783(10) 134.6 . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.550 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.085 # Attachment '- 6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 853364' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H46.50 Co N4 O17.25' _chemical_formula_weight 822.16 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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.738(2) _cell_length_b 11.204(3) _cell_length_c 17.566(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.186(3) _cell_angle_gamma 90.00 _cell_volume 1873.3(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2172 _cell_measurement_theta_min 2.171 _cell_measurement_theta_max 25.281 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 863 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8423 _exptl_absorpt_correction_T_max 0.9046 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9534 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3490 _reflns_number_gt 2875 _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^)+(0.0548P)^2^+0.9498P] 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 3490 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0927(3) -0.1128(3) 0.11748(17) 0.0255(7) Uani 1 1 d . . . H1 H -0.0673 -0.1727 0.1544 0.031 Uiso 1 1 calc R . . C2 C -0.1736(3) -0.1409(3) 0.04486(18) 0.0335(8) Uani 1 1 d . . . H2 H -0.2034 -0.2190 0.0336 0.040 Uiso 1 1 calc R . . C3 C -0.2097(3) -0.0530(3) -0.01053(18) 0.0333(8) Uani 1 1 d . . . H3 H -0.2650 -0.0718 -0.0590 0.040 Uiso 1 1 calc R . . C4 C -0.1648(3) 0.0619(3) 0.00524(16) 0.0274(7) Uani 1 1 d . . . H4A H -0.1877 0.1206 -0.0327 0.033 Uiso 1 1 calc R . . C5 C -0.0840(3) 0.0905(3) 0.07891(16) 0.0208(6) Uani 1 1 d . . . C6 C -0.0491(3) 0.0036(3) 0.13596(16) 0.0193(6) Uani 1 1 d . . . C7 C 0.0413(3) 0.0348(2) 0.21483(15) 0.0163(6) Uani 1 1 d . . . C8 C 0.1833(3) -0.0297(3) 0.22469(15) 0.0177(6) Uani 1 1 d . . . C9 C 0.0596(3) 0.1709(2) 0.22659(15) 0.0171(6) Uani 1 1 d . . . H9 H 0.1501 0.1884 0.2613 0.021 Uiso 1 1 calc R . . C10 C 0.0359(3) 0.2529(3) 0.15860(16) 0.0203(6) Uani 1 1 d . . . C11 C 0.4093(3) 0.2649(3) 0.15800(16) 0.0218(6) Uani 1 1 d . . . H11 H 0.3543 0.2711 0.1951 0.026 Uiso 1 1 calc R . . C12 C 0.3959(3) 0.3514(3) 0.10142(17) 0.0261(7) Uani 1 1 d . . . H12 H 0.3319 0.4132 0.1004 0.031 Uiso 1 1 calc R . . C13 C 0.4777(3) 0.3465(3) 0.04599(16) 0.0256(7) Uani 1 1 d . . . C14 C 0.4688(4) 0.4412(3) -0.01592(18) 0.0343(8) Uani 1 1 d . . . H14A H 0.3710 0.4533 -0.0408 0.041 Uiso 1 1 calc R . . H14B H 0.5176 0.4133 -0.0553 0.041 Uiso 1 1 calc R . . C15 C 0.5682(3) 0.2504(3) 0.05017(18) 0.0315(7) Uani 1 1 d . . . H15 H 0.6243 0.2425 0.0137 0.038 Uiso 1 1 calc R . . C16 C 0.5755(3) 0.1661(3) 0.10824(17) 0.0248(7) Uani 1 1 d . . . H16 H 0.6373 0.1025 0.1098 0.030 Uiso 1 1 calc R . . Co1 Co 0.5000 0.03716(5) 0.2500 0.01547(16) Uani 1 2 d S . . N1 N 0.4977(2) 0.1720(2) 0.16237(13) 0.0192(5) Uani 1 1 d . . . N2 N -0.0371(2) 0.2095(2) 0.09175(13) 0.0232(6) Uani 1 1 d . . . H2A H -0.0575 0.2581 0.0531 0.028 Uiso 1 1 calc R . . O1 O 0.28448(19) 0.03677(18) 0.21904(12) 0.0242(5) Uani 1 1 d . . . O2 O 0.1901(2) -0.13966(18) 0.23548(12) 0.0284(5) Uani 1 1 d . . . O3 O 0.0768(2) 0.35773(18) 0.16524(12) 0.0285(5) Uani 1 1 d . . . O4 O 0.5284(2) -0.09547(18) 0.16642(12) 0.0284(5) Uani 1 1 d . . . H4C H 0.4772 -0.1574 0.1636 0.034 Uiso 1 1 d R . . H4D H 0.6072 -0.1291 0.1834 0.034 Uiso 1 1 d R . . O5 O 0.2739(3) 0.4538(3) 0.28920(16) 0.0633(9) Uani 1 1 d . . . O6 O 0.5000 0.5642(3) 0.2500 0.0416(8) Uani 1 2 d S . . O7 O 0.6670(2) 0.7225(2) 0.34787(12) 0.0327(5) Uani 1 1 d . . . O8 O 0.8995(3) 0.5330(3) 0.0943(2) 0.0737(10) Uani 1 1 d . . . H8A H 0.9509 0.4794 0.1186 0.088 Uiso 1 1 d R . . H8B H 0.8627 0.5296 0.0468 0.088 Uiso 1 1 d R . . O9 O 0.8750(3) 0.6278(2) 0.46359(13) 0.0445(6) Uani 1 1 d . . . H7B H 0.7165 0.7617 0.3221 0.053 Uiso 1 1 d R . . H7A H 0.6118 0.6724 0.3207 0.053 Uiso 1 1 d R . . H5A H 0.2174 0.4309 0.2482 0.053 Uiso 1 1 d R . . H9B H 0.9474 0.6078 0.4467 0.053 Uiso 1 1 d R . . H6A H 0.4423 0.5229 0.2691 0.053 Uiso 1 1 d R . . H5B H 0.2332 0.4935 0.3193 0.053 Uiso 1 1 d R . . H9A H 0.8100 0.6506 0.4262 0.053 Uiso 1 1 d R . . O10 O 1.0000 0.6599(14) 0.2500 0.096(8) Uani 0.25 2 d SP . . H10 H 0.9242 0.6210 0.2349 0.115 Uiso 0.25 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0243(15) 0.0279(17) 0.0252(15) -0.0031(14) 0.0074(12) -0.0061(14) C2 0.0324(17) 0.037(2) 0.0308(17) -0.0118(16) 0.0063(14) -0.0135(15) C3 0.0227(16) 0.051(2) 0.0233(16) -0.0145(16) -0.0006(12) -0.0033(16) C4 0.0213(15) 0.043(2) 0.0172(14) -0.0030(14) 0.0014(12) 0.0037(14) C5 0.0164(14) 0.0281(16) 0.0195(14) -0.0027(13) 0.0073(11) 0.0010(12) C6 0.0119(13) 0.0285(16) 0.0180(14) -0.0032(12) 0.0043(10) -0.0009(12) C7 0.0120(12) 0.0195(15) 0.0183(13) 0.0003(12) 0.0047(10) -0.0007(12) C8 0.0169(13) 0.0219(16) 0.0146(13) -0.0008(12) 0.0041(10) 0.0007(12) C9 0.0114(13) 0.0214(15) 0.0182(14) -0.0006(12) 0.0021(11) -0.0009(11) C10 0.0169(14) 0.0240(16) 0.0212(15) 0.0024(13) 0.0067(11) 0.0002(13) C11 0.0209(15) 0.0220(16) 0.0241(15) 0.0001(13) 0.0084(12) -0.0009(12) C12 0.0258(16) 0.0220(16) 0.0299(16) 0.0037(14) 0.0046(13) 0.0028(13) C13 0.0312(16) 0.0228(16) 0.0211(15) 0.0020(13) 0.0018(12) -0.0053(13) C14 0.045(2) 0.0311(18) 0.0268(16) 0.0094(15) 0.0081(14) -0.0026(16) C15 0.0324(17) 0.0373(19) 0.0294(17) 0.0049(15) 0.0171(14) 0.0000(15) C16 0.0225(15) 0.0253(16) 0.0289(16) 0.0025(13) 0.0106(12) 0.0033(13) Co1 0.0114(3) 0.0171(3) 0.0180(3) 0.000 0.00344(19) 0.000 N1 0.0148(11) 0.0222(13) 0.0204(12) 0.0014(10) 0.0030(9) -0.0008(10) N2 0.0252(13) 0.0270(14) 0.0169(12) 0.0039(11) 0.0029(10) 0.0036(11) O1 0.0132(9) 0.0258(11) 0.0332(11) 0.0042(10) 0.0041(8) -0.0013(9) O2 0.0238(11) 0.0196(12) 0.0447(13) 0.0031(10) 0.0141(9) 0.0036(9) O3 0.0335(12) 0.0193(11) 0.0315(12) 0.0045(9) 0.0039(9) -0.0035(10) O4 0.0252(11) 0.0247(12) 0.0353(12) -0.0045(10) 0.0065(9) -0.0014(9) O5 0.0404(15) 0.092(2) 0.0555(17) -0.0212(17) 0.0059(13) -0.0163(16) O6 0.0390(19) 0.036(2) 0.048(2) 0.000 0.0057(16) 0.000 O7 0.0302(12) 0.0314(13) 0.0367(12) 0.0036(10) 0.0076(10) -0.0038(10) O8 0.0611(19) 0.069(2) 0.091(2) 0.0338(19) 0.0151(17) 0.0249(17) O9 0.0479(15) 0.0476(16) 0.0346(13) -0.0051(12) 0.0010(11) 0.0084(13) O10 0.23(3) 0.035(9) 0.032(9) 0.000 0.039(12) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.387(4) . ? C1 C6 1.389(4) . ? C1 H1 0.9300 . ? C2 C3 1.377(5) . ? C2 H2 0.9300 . ? C3 C4 1.368(5) . ? C3 H3 0.9300 . ? C4 C5 1.402(4) . ? C4 H4A 0.9300 . ? C5 C6 1.387(4) . ? C5 N2 1.412(4) . ? C6 C7 1.517(4) . ? C7 C8 1.537(4) . ? C7 C9 1.544(4) . ? C7 C7 1.611(5) 2 ? C8 O2 1.246(3) . ? C8 O1 1.256(3) . ? C9 C10 1.486(4) . ? C9 C9 1.558(5) 2 ? C9 H9 0.9800 . ? C10 O3 1.238(3) . ? C10 N2 1.330(4) . ? C11 N1 1.342(4) . ? C11 C12 1.374(4) . ? C11 H11 0.9300 . ? C12 C13 1.383(4) . ? C12 H12 0.9300 . ? C13 C15 1.383(4) . ? C13 C14 1.509(4) . ? C14 C14 1.509(6) 3_665 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.381(4) . ? C15 H15 0.9300 . ? C16 N1 1.337(3) . ? C16 H16 0.9300 . ? Co1 O1 2.0539(19) 2_655 ? Co1 O1 2.0539(19) . ? Co1 O4 2.148(2) . ? Co1 O4 2.148(2) 2_655 ? Co1 N1 2.154(2) . ? Co1 N1 2.154(2) 2_655 ? N2 H2A 0.8600 . ? O4 H4C 0.8500 . ? O4 H4D 0.8500 . ? O5 H5A 0.8494 . ? O5 H5B 0.8504 . ? O6 H6A 0.8499 . ? O7 H7B 0.8502 . ? O7 H7A 0.8505 . ? O8 H8A 0.8388 . ? O8 H8B 0.8362 . ? O9 H9B 0.8500 . ? O9 H9A 0.8500 . ? O10 H10 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.0(3) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C6 C5 C4 120.7(3) . . ? C6 C5 N2 121.7(2) . . ? C4 C5 N2 117.6(3) . . ? C5 C6 C1 118.3(3) . . ? C5 C6 C7 120.3(3) . . ? C1 C6 C7 121.3(3) . . ? C6 C7 C8 109.3(2) . . ? C6 C7 C9 112.2(2) . . ? C8 C7 C9 111.9(2) . . ? C6 C7 C7 114.4(2) . 2 ? C8 C7 C7 119.8(2) . 2 ? C9 C7 C7 87.67(13) . 2 ? O2 C8 O1 125.5(2) . . ? O2 C8 C7 120.0(2) . . ? O1 C8 C7 114.5(2) . . ? C10 C9 C7 120.6(2) . . ? C10 C9 C9 114.7(2) . 2 ? C7 C9 C9 89.61(13) . 2 ? C10 C9 H9 110.1 . . ? C7 C9 H9 110.1 . . ? C9 C9 H9 110.1 2 . ? O3 C10 N2 122.1(3) . . ? O3 C10 C9 121.3(2) . . ? N2 C10 C9 116.6(3) . . ? N1 C11 C12 123.3(3) . . ? N1 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C15 C13 C12 116.7(3) . . ? C15 C13 C14 121.6(3) . . ? C12 C13 C14 121.7(3) . . ? C13 C14 C14 112.9(3) . 3_665 ? C13 C14 H14A 109.0 . . ? C14 C14 H14A 109.0 3_665 . ? C13 C14 H14B 109.0 . . ? C14 C14 H14B 109.0 3_665 . ? H14A C14 H14B 107.8 . . ? C16 C15 C13 120.3(3) . . ? C16 C15 H15 119.9 . . ? C13 C15 H15 119.9 . . ? N1 C16 C15 122.9(3) . . ? N1 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? O1 Co1 O1 179.76(12) 2_655 . ? O1 Co1 O4 84.69(8) 2_655 . ? O1 Co1 O4 95.14(8) . . ? O1 Co1 O4 95.14(8) 2_655 2_655 ? O1 Co1 O4 84.69(8) . 2_655 ? O4 Co1 O4 92.43(11) . 2_655 ? O1 Co1 N1 92.68(8) 2_655 . ? O1 Co1 N1 87.49(8) . . ? O4 Co1 N1 88.87(8) . . ? O4 Co1 N1 172.16(8) 2_655 . ? O1 Co1 N1 87.49(8) 2_655 2_655 ? O1 Co1 N1 92.68(8) . 2_655 ? O4 Co1 N1 172.16(8) . 2_655 ? O4 Co1 N1 88.87(8) 2_655 2_655 ? N1 Co1 N1 90.89(13) . 2_655 ? C16 N1 C11 116.8(2) . . ? C16 N1 Co1 123.5(2) . . ? C11 N1 Co1 119.65(18) . . ? C10 N2 C5 125.5(2) . . ? C10 N2 H2A 117.3 . . ? C5 N2 H2A 117.3 . . ? C8 O1 Co1 139.06(18) . . ? Co1 O4 H4C 116.5 . . ? Co1 O4 H4D 107.7 . . ? H4C O4 H4D 97.7 . . ? H5A O5 H5B 112.5 . . ? H7B O7 H7A 113.9 . . ? H8A O8 H8B 124.0 . . ? H9B O9 H9A 110.2 . . ? 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 C6 C1 C2 C3 1.1(4) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C2 C3 C4 C5 -1.4(4) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? C3 C4 C5 N2 178.4(3) . . . . ? C4 C5 C6 C1 1.8(4) . . . . ? N2 C5 C6 C1 -176.5(2) . . . . ? C4 C5 C6 C7 178.5(2) . . . . ? N2 C5 C6 C7 0.2(4) . . . . ? C2 C1 C6 C5 -2.4(4) . . . . ? C2 C1 C6 C7 -179.0(3) . . . . ? C5 C6 C7 C8 -113.3(3) . . . . ? C1 C6 C7 C8 63.3(3) . . . . ? C5 C6 C7 C9 11.4(3) . . . . ? C1 C6 C7 C9 -172.0(2) . . . . ? C5 C6 C7 C7 109.3(2) . . . 2 ? C1 C6 C7 C7 -74.1(3) . . . 2 ? C6 C7 C8 O2 -72.1(3) . . . . ? C9 C7 C8 O2 163.0(2) . . . . ? C7 C7 C8 O2 62.6(3) 2 . . . ? C6 C7 C8 O1 106.3(3) . . . . ? C9 C7 C8 O1 -18.6(3) . . . . ? C7 C7 C8 O1 -118.9(2) 2 . . . ? C6 C7 C9 C10 -20.6(3) . . . . ? C8 C7 C9 C10 102.6(3) . . . . ? C7 C7 C9 C10 -136.1(2) 2 . . . ? C6 C7 C9 C9 98.2(3) . . . 2 ? C8 C7 C9 C9 -138.6(2) . . . 2 ? C7 C7 C9 C9 -17.3(3) 2 . . 2 ? C7 C9 C10 O3 -165.1(2) . . . . ? C9 C9 C10 O3 89.6(3) 2 . . . ? C7 C9 C10 N2 18.1(3) . . . . ? C9 C9 C10 N2 -87.2(3) 2 . . . ? N1 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C15 1.5(4) . . . . ? C11 C12 C13 C14 -178.5(3) . . . . ? C15 C13 C14 C14 -108.8(4) . . . 3_665 ? C12 C13 C14 C14 71.1(5) . . . 3_665 ? C12 C13 C15 C16 -1.0(5) . . . . ? C14 C13 C15 C16 179.0(3) . . . . ? C13 C15 C16 N1 0.1(5) . . . . ? C15 C16 N1 C11 0.3(4) . . . . ? C15 C16 N1 Co1 176.9(2) . . . . ? C12 C11 N1 C16 0.2(4) . . . . ? C12 C11 N1 Co1 -176.5(2) . . . . ? O1 Co1 N1 C16 49.7(2) 2_655 . . . ? O1 Co1 N1 C16 -130.1(2) . . . . ? O4 Co1 N1 C16 -34.9(2) . . . . ? O4 Co1 N1 C16 -134.6(6) 2_655 . . . ? N1 Co1 N1 C16 137.2(2) 2_655 . . . ? O1 Co1 N1 C11 -133.8(2) 2_655 . . . ? O1 Co1 N1 C11 46.4(2) . . . . ? O4 Co1 N1 C11 141.6(2) . . . . ? O4 Co1 N1 C11 41.9(7) 2_655 . . . ? N1 Co1 N1 C11 -46.26(18) 2_655 . . . ? O3 C10 N2 C5 178.1(3) . . . . ? C9 C10 N2 C5 -5.1(4) . . . . ? C6 C5 N2 C10 -4.1(4) . . . . ? C4 C5 N2 C10 177.5(3) . . . . ? O2 C8 O1 Co1 -21.7(5) . . . . ? C7 C8 O1 Co1 159.98(19) . . . . ? O1 Co1 O1 C8 25.5(3) 2_655 . . . ? O4 Co1 O1 C8 71.5(3) . . . . ? O4 Co1 O1 C8 -20.5(3) 2_655 . . . ? N1 Co1 O1 C8 160.1(3) . . . . ? N1 Co1 O1 C8 -109.1(3) 2_655 . . . ? 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 N2 H2A O9 0.86 2.03 2.882(3) 174.4 4_465 O4 H4C O7 0.85 1.92 2.765(3) 169.5 2_645 O4 H4D O2 0.85 2.18 2.955(3) 151.5 2_655 O8 H8A O3 0.84 1.90 2.735(3) 174.2 1_655 O8 H8B O9 0.84 2.31 2.888(4) 126.7 4_565 O7 H7B O2 0.85 1.86 2.707(3) 173.8 2_665 O7 H7A O6 0.85 1.90 2.750(3) 173.0 . O5 H5A O3 0.85 1.96 2.796(3) 170.2 . O9 H9B O8 0.85 1.97 2.815(4) 169.9 2_755 O6 H6A O5 0.85 1.91 2.737(3) 163.2 . O5 H5B O8 0.85 2.24 3.047(4) 159.7 2_655 O9 H9A O7 0.85 1.92 2.761(3) 172.5 . O10 H10 O8 0.85 2.62 3.055(8) 112.8 . O10 H10 O5 0.85 2.66 3.485(11) 164.7 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.553 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.072 # Attachment '- 7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 853365' #TrackingRef '- 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 Mn N4 O12' _chemical_formula_weight 723.59 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.367(3) _cell_length_b 17.381(2) _cell_length_c 18.152(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.306(2) _cell_angle_gamma 90.00 _cell_volume 6322.2(15) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3560 _cell_measurement_theta_min 2.392 _cell_measurement_theta_max 25.611 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3016 _exptl_absorpt_coefficient_mu 0.491 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8955 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 16374 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5879 _reflns_number_gt 4399 _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^)+(0.0648P)^2^+6.3335P] 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 5879 _refine_ls_number_parameters 447 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.87593(16) 0.21487(18) 0.8289(2) 0.0337(7) Uani 1 1 d . . . H1 H 0.8325 0.2211 0.7942 0.040 Uiso 1 1 calc R . . C2 C 0.92708(18) 0.2570(2) 0.8177(2) 0.0471(9) Uani 1 1 d . . . H2 H 0.9178 0.2902 0.7750 0.057 Uiso 1 1 calc R . . C3 C 0.99133(19) 0.2499(2) 0.8692(3) 0.0501(10) Uani 1 1 d . . . H3 H 1.0255 0.2787 0.8620 0.060 Uiso 1 1 calc R . . C4 C 1.00481(17) 0.20007(19) 0.9315(2) 0.0409(9) Uani 1 1 d . . . H4 H 1.0482 0.1952 0.9667 0.049 Uiso 1 1 calc R . . C5 C 0.95419(15) 0.15712(17) 0.94230(19) 0.0300(7) Uani 1 1 d . . . C6 C 0.88839(15) 0.16375(16) 0.89068(18) 0.0263(7) Uani 1 1 d . . . C7 C 0.83396(14) 0.11713(16) 0.90622(17) 0.0237(6) Uani 1 1 d . . . C8 C 0.86460(14) 0.04541(16) 0.95535(17) 0.0246(6) Uani 1 1 d . . . H8 H 0.8332 0.0249 0.9789 0.030 Uiso 1 1 calc R . . C9 C 0.93254(15) 0.05030(17) 1.01681(19) 0.0296(7) Uani 1 1 d . . . C10 C 0.79021(14) 0.16811(15) 0.93786(17) 0.0211(6) Uani 1 1 d . . . C11 C 0.85436(15) 0.00265(16) 0.87623(18) 0.0267(7) Uani 1 1 d . . . H11 H 0.8917 0.0133 0.8582 0.032 Uiso 1 1 calc R . . C12 C 0.79580(14) 0.05860(15) 0.83662(17) 0.0228(6) Uani 1 1 d . . . C13 C 0.78327(15) 0.08454(16) 0.75147(18) 0.0269(7) Uani 1 1 d . . . C14 C 0.84216(15) -0.08187(16) 0.87590(18) 0.0283(7) Uani 1 1 d . . . C15 C 0.72681(15) -0.05190(17) 0.85999(18) 0.0296(7) Uani 1 1 d . . . C16 C 0.66841(17) -0.08189(19) 0.8644(2) 0.0380(8) Uani 1 1 d . . . H16 H 0.6663 -0.1337 0.8761 0.046 Uiso 1 1 calc R . . C17 C 0.61331(17) -0.0359(2) 0.8517(2) 0.0406(8) Uani 1 1 d . . . H17 H 0.5742 -0.0566 0.8549 0.049 Uiso 1 1 calc R . . C18 C 0.61605(16) 0.0413(2) 0.8340(2) 0.0393(8) Uani 1 1 d . . . H18 H 0.5787 0.0725 0.8243 0.047 Uiso 1 1 calc R . . C19 C 0.67506(15) 0.07130(18) 0.83092(18) 0.0312(7) Uani 1 1 d . . . H19 H 0.6769 0.1233 0.8197 0.037 Uiso 1 1 calc R . . C20 C 0.73166(15) 0.02655(16) 0.84395(17) 0.0258(6) Uani 1 1 d . . . C21 C 0.68483(16) 0.10090(18) 1.1588(2) 0.0336(7) Uani 1 1 d . . . H21 H 0.6939 0.1426 1.1930 0.040 Uiso 1 1 calc R . . C22 C 0.63544(18) 0.0506(2) 1.1594(2) 0.0425(9) Uani 1 1 d . . . H22 H 0.6117 0.0593 1.1929 0.051 Uiso 1 1 calc R . . C23 C 0.62089(17) -0.0118(2) 1.1112(2) 0.0398(8) Uani 1 1 d . . . C24 C 0.65799(18) -0.0212(2) 1.0632(2) 0.0427(9) Uani 1 1 d . . . H24 H 0.6505 -0.0632 1.0295 0.051 Uiso 1 1 calc R . . C25 C 0.70641(16) 0.03214(18) 1.0652(2) 0.0366(8) Uani 1 1 d . . . H25 H 0.7307 0.0250 1.0320 0.044 Uiso 1 1 calc R . . C26 C 0.5658(2) -0.0654(3) 1.1133(3) 0.0773(16) Uani 1 1 d . . . H26A H 0.5746 -0.0786 1.1679 0.093 Uiso 1 1 calc R . . H26B H 0.5246 -0.0360 1.0960 0.093 Uiso 1 1 calc R . . C27 C 0.5531(2) -0.1354(2) 1.0700(3) 0.0638(13) Uani 1 1 d . . . H27A H 0.5931 -0.1669 1.0868 0.077 Uiso 1 1 calc R . . H27B H 0.5423 -0.1242 1.0146 0.077 Uiso 1 1 calc R . . C28 C 0.49632(18) -0.17959(19) 1.0815(3) 0.0457(10) Uani 1 1 d . . . C29 C 0.50675(19) -0.2335(2) 1.1397(3) 0.0726(15) Uani 1 1 d . . . H29 H 0.5499 -0.2456 1.1721 0.087 Uiso 1 1 calc R . . C30 C 0.45323(18) -0.2696(2) 1.1497(3) 0.0637(13) Uani 1 1 d . . . H30 H 0.4619 -0.3075 1.1882 0.076 Uiso 1 1 calc R . . C31 C 0.38084(16) -0.20207(18) 1.05312(19) 0.0330(7) Uani 1 1 d . . . H31 H 0.3371 -0.1900 1.0225 0.040 Uiso 1 1 calc R . . C32 C 0.43127(18) -0.16463(19) 1.0379(2) 0.0418(9) Uani 1 1 d . . . H32 H 0.4212 -0.1287 0.9975 0.050 Uiso 1 1 calc R . . Mn1 Mn 0.80231(2) 0.18017(2) 1.12052(3) 0.02128(14) Uani 1 1 d . . . N1 N 0.97142(13) 0.10708(14) 1.00768(16) 0.0338(6) Uani 1 1 d . . . H1A H 1.0095 0.1136 1.0441 0.041 Uiso 1 1 calc R . . N2 N 0.78050(13) -0.10262(14) 0.86968(15) 0.0314(6) Uani 1 1 d . . . H2A H 0.7728 -0.1510 0.8717 0.038 Uiso 1 1 calc R . . N3 N 0.72012(12) 0.09311(13) 1.11228(15) 0.0272(6) Uani 1 1 d . . . N4 N 0.39038(12) -0.25447(14) 1.10879(15) 0.0285(6) Uani 1 1 d . . . O1 O 0.95180(12) 0.00520(13) 1.07230(14) 0.0425(6) Uani 1 1 d . . . O3 O 0.88603(11) -0.12989(12) 0.88088(14) 0.0386(6) Uani 1 1 d . . . O4 O 0.81581(12) 0.05113(13) 0.71616(14) 0.0418(6) Uani 1 1 d . . . O5 O 0.74198(11) 0.13734(12) 0.72497(12) 0.0358(5) Uani 1 1 d . . . O6 O 0.78472(10) 0.14859(11) 1.00105(12) 0.0297(5) Uani 1 1 d . . . O7 O 0.76433(10) 0.22555(11) 0.89792(12) 0.0302(5) Uani 1 1 d . . . O8 O 0.82087(12) 0.22539(13) 1.24279(13) 0.0385(6) Uani 1 1 d . . . O9 O 0.86491(11) 0.08564(12) 1.18405(15) 0.0417(6) Uani 1 1 d . . . O11 O 0.5000 0.4111(5) 0.2500 0.165(7) Uani 0.50 2 d SPU . . H15A H 0.2415 0.2843 0.1531 0.198 Uiso 1 1 d R . . H13A H 0.3217 0.4244 0.1012 0.198 Uiso 1 1 d R . . H11A H 0.5337 0.3822 0.2697 0.198 Uiso 0.50 1 d PR . . H11B H 0.4752 0.4063 0.2776 0.198 Uiso 0.50 1 d PR . . O12 O 0.4961(4) 0.5552(3) 0.2712(3) 0.0527(17) Uani 0.50 1 d P . . O13 O 0.3523(2) 0.4050(2) 0.0870(2) 0.1002(13) Uani 1 1 d . . . O14 O 0.34126(15) 0.25321(16) 0.05152(19) 0.0678(8) Uani 1 1 d . . . O15 O 0.23824(14) 0.26308(14) 0.10972(16) 0.0584(8) Uani 1 1 d . . . H13B H 0.3845 0.3888 0.1265 0.070 Uiso 1 1 d R . . H15B H 0.2735 0.2689 0.0987 0.070 Uiso 1 1 d R . . H14B H 0.3431 0.3019 0.0566 0.070 Uiso 1 1 d R . . H14A H 0.3180 0.2455 0.0036 0.070 Uiso 1 1 d R . . H8A H 0.8416 0.2030 1.2861 0.070 Uiso 1 1 d R . . H9B H 0.8486 0.0442 1.1947 0.070 Uiso 1 1 d R . . H9A H 0.9070 0.0832 1.2074 0.070 Uiso 1 1 d R . . H8B H 0.8022 0.2668 1.2492 0.070 Uiso 1 1 d R . . H12A H 0.5000 0.5110 0.2500 0.070 Uiso 1 2 d SR . . H12B H 0.5049 0.5432 0.3192 0.070 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0330(18) 0.0295(16) 0.0403(19) 0.0059(15) 0.0150(16) 0.0024(14) C2 0.048(2) 0.039(2) 0.061(3) 0.0149(18) 0.027(2) -0.0030(17) C3 0.039(2) 0.047(2) 0.073(3) 0.007(2) 0.031(2) -0.0076(17) C4 0.0262(18) 0.041(2) 0.056(2) -0.0022(18) 0.0156(17) -0.0050(15) C5 0.0273(17) 0.0279(16) 0.0354(18) -0.0049(14) 0.0117(15) 0.0020(13) C6 0.0269(17) 0.0210(15) 0.0341(17) -0.0022(13) 0.0145(14) 0.0014(12) C7 0.0242(16) 0.0216(14) 0.0243(15) -0.0006(12) 0.0072(13) -0.0006(12) C8 0.0254(16) 0.0225(15) 0.0266(16) 0.0006(12) 0.0100(13) 0.0003(12) C9 0.0281(17) 0.0276(16) 0.0328(18) -0.0068(14) 0.0102(14) 0.0033(13) C10 0.0196(15) 0.0215(15) 0.0221(15) -0.0035(12) 0.0069(12) -0.0031(11) C11 0.0255(16) 0.0227(15) 0.0333(17) 0.0016(13) 0.0119(14) 0.0031(12) C12 0.0239(15) 0.0204(14) 0.0242(15) -0.0011(12) 0.0084(13) 0.0035(12) C13 0.0301(17) 0.0219(15) 0.0289(17) -0.0049(13) 0.0106(14) -0.0037(13) C14 0.0324(18) 0.0246(16) 0.0247(16) -0.0028(13) 0.0060(14) 0.0014(14) C15 0.0312(17) 0.0267(16) 0.0301(17) -0.0037(13) 0.0095(14) -0.0014(13) C16 0.040(2) 0.0330(18) 0.043(2) -0.0004(15) 0.0184(17) -0.0061(15) C17 0.0315(19) 0.049(2) 0.046(2) -0.0056(17) 0.0188(17) -0.0101(16) C18 0.0285(18) 0.045(2) 0.044(2) -0.0095(17) 0.0121(16) -0.0003(15) C19 0.0304(18) 0.0288(16) 0.0335(18) -0.0072(14) 0.0100(15) -0.0020(13) C20 0.0290(17) 0.0264(15) 0.0202(15) -0.0014(13) 0.0062(13) -0.0015(13) C21 0.0371(19) 0.0298(17) 0.0362(18) -0.0026(14) 0.0156(16) -0.0082(14) C22 0.044(2) 0.047(2) 0.046(2) -0.0054(17) 0.0268(18) -0.0119(17) C23 0.039(2) 0.044(2) 0.039(2) -0.0032(16) 0.0169(17) -0.0183(16) C24 0.049(2) 0.0374(19) 0.044(2) -0.0114(16) 0.0204(19) -0.0191(17) C25 0.0369(19) 0.0370(18) 0.041(2) -0.0026(16) 0.0203(17) -0.0094(15) C26 0.090(4) 0.080(3) 0.084(3) -0.038(3) 0.059(3) -0.060(3) C27 0.048(2) 0.048(2) 0.115(4) -0.019(2) 0.053(3) -0.0202(19) C28 0.037(2) 0.0294(18) 0.082(3) -0.0105(19) 0.034(2) -0.0100(15) C29 0.021(2) 0.052(2) 0.131(4) 0.034(3) 0.009(2) -0.0024(18) C30 0.033(2) 0.049(2) 0.091(3) 0.038(2) -0.001(2) -0.0096(18) C31 0.0282(17) 0.0336(17) 0.0327(18) 0.0026(14) 0.0051(15) -0.0066(14) C32 0.048(2) 0.0383(19) 0.040(2) 0.0030(16) 0.0167(18) -0.0152(16) Mn1 0.0200(2) 0.0190(2) 0.0256(2) 0.00093(18) 0.00897(19) -0.00203(18) N1 0.0230(14) 0.0365(15) 0.0363(15) -0.0017(13) 0.0031(12) -0.0016(12) N2 0.0357(16) 0.0183(12) 0.0401(16) 0.0002(12) 0.0131(13) -0.0004(11) N3 0.0256(13) 0.0232(13) 0.0341(15) 0.0023(11) 0.0121(12) -0.0044(10) N4 0.0210(14) 0.0282(13) 0.0343(15) 0.0018(11) 0.0071(12) -0.0051(10) O1 0.0400(14) 0.0406(13) 0.0383(14) 0.0119(11) 0.0026(11) 0.0044(11) O3 0.0351(13) 0.0250(11) 0.0513(15) -0.0053(10) 0.0095(12) 0.0065(10) O4 0.0599(16) 0.0376(13) 0.0378(14) 0.0000(11) 0.0293(13) 0.0101(11) O5 0.0423(14) 0.0338(12) 0.0308(12) 0.0047(10) 0.0120(11) 0.0091(11) O6 0.0351(13) 0.0290(11) 0.0292(12) -0.0051(9) 0.0165(10) -0.0043(9) O7 0.0324(12) 0.0249(11) 0.0335(12) 0.0004(10) 0.0119(10) 0.0079(9) O8 0.0484(14) 0.0383(13) 0.0267(12) 0.0024(10) 0.0104(11) 0.0109(11) O9 0.0289(12) 0.0302(12) 0.0616(16) 0.0179(11) 0.0101(12) 0.0022(10) O11 0.221(14) 0.026(4) 0.125(9) 0.000 -0.096(9) 0.000 O12 0.043(3) 0.053(3) 0.053(5) 0.005(2) 0.005(4) -0.002(3) O13 0.141(3) 0.079(2) 0.114(3) -0.036(2) 0.086(3) -0.034(2) O14 0.0605(19) 0.0618(18) 0.081(2) 0.0031(16) 0.0246(17) -0.0090(15) O15 0.082(2) 0.0423(15) 0.0667(19) -0.0112(13) 0.0460(17) -0.0158(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 C1 C6 1.382(4) . ? C1 C2 1.388(4) . ? C1 H1 0.9300 . ? C2 C3 1.372(5) . ? C2 H2 0.9300 . ? C3 C4 1.374(5) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.398(4) . ? C5 N1 1.413(4) . ? C6 C7 1.522(4) . ? C7 C10 1.537(4) . ? C7 C8 1.540(4) . ? C7 C12 1.607(4) . ? C8 C9 1.495(4) . ? C8 C11 1.564(4) . ? C8 H8 0.9800 . ? C9 O1 1.229(4) . ? C9 N1 1.337(4) . ? C10 O6 1.240(3) . ? C10 O7 1.245(3) . ? C11 C14 1.492(4) . ? C11 C12 1.550(4) . ? C11 H11 0.9800 . ? C12 C20 1.527(4) . ? C12 C13 1.542(4) . ? C13 O4 1.241(3) . ? C13 O5 1.248(4) . ? C14 O3 1.235(3) . ? C14 N2 1.332(4) . ? C15 C16 1.380(4) . ? C15 C20 1.406(4) . ? C15 N2 1.409(4) . ? C16 C17 1.374(5) . ? C16 H16 0.9300 . ? C17 C18 1.386(5) . ? C17 H17 0.9300 . ? C18 C19 1.383(4) . ? C18 H18 0.9300 . ? C19 C20 1.387(4) . ? C19 H19 0.9300 . ? C21 N3 1.320(4) . ? C21 C22 1.373(4) . ? C21 H21 0.9300 . ? C22 C23 1.360(5) . ? C22 H22 0.9300 . ? C23 C24 1.377(5) . ? C23 C26 1.511(5) . ? C24 C25 1.380(4) . ? C24 H24 0.9300 . ? C25 N3 1.328(4) . ? C25 H25 0.9300 . ? C26 C27 1.424(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.511(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C32 1.365(5) . ? C28 C29 1.371(6) . ? C29 C30 1.371(5) . ? C29 H29 0.9300 . ? C30 N4 1.316(4) . ? C30 H30 0.9300 . ? C31 N4 1.323(4) . ? C31 C32 1.367(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? Mn1 O7 2.120(2) 7_657 ? Mn1 O6 2.140(2) . ? Mn1 O9 2.179(2) . ? Mn1 O8 2.256(2) . ? Mn1 N4 2.271(2) 3 ? Mn1 N3 2.283(2) . ? N1 H1A 0.8600 . ? N2 H2A 0.8600 . ? N4 Mn1 2.271(2) 3_445 ? O7 Mn1 2.120(2) 7_657 ? O8 H8A 0.8512 . ? O8 H8B 0.8510 . ? O9 H9B 0.8513 . ? O9 H9A 0.8518 . ? O11 H11A 0.8499 . ? O11 H11B 0.8501 . ? O12 O12 0.842(9) 2_655 ? O12 H12A 0.8762 . ? O12 H12B 0.8507 . ? O13 H13A 0.8506 . ? O13 H13B 0.8510 . ? O14 H14B 0.8499 . ? O14 H14A 0.8490 . ? O15 H15A 0.8504 . ? O15 H15B 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.2(3) . . ? C6 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 121.0(3) . . ? C4 C5 N1 117.5(3) . . ? C6 C5 N1 121.5(3) . . ? C1 C6 C5 117.6(3) . . ? C1 C6 C7 123.2(3) . . ? C5 C6 C7 119.2(3) . . ? C6 C7 C10 111.4(2) . . ? C6 C7 C8 109.9(2) . . ? C10 C7 C8 116.2(2) . . ? C6 C7 C12 113.8(2) . . ? C10 C7 C12 116.8(2) . . ? C8 C7 C12 86.6(2) . . ? C9 C8 C7 119.6(2) . . ? C9 C8 C11 120.2(2) . . ? C7 C8 C11 87.5(2) . . ? C9 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? C11 C8 H8 109.2 . . ? O1 C9 N1 121.8(3) . . ? O1 C9 C8 122.5(3) . . ? N1 C9 C8 115.7(3) . . ? O6 C10 O7 126.3(3) . . ? O6 C10 C7 116.9(2) . . ? O7 C10 C7 116.7(2) . . ? C14 C11 C12 120.3(3) . . ? C14 C11 C8 116.1(2) . . ? C12 C11 C8 87.8(2) . . ? C14 C11 H11 110.3 . . ? C12 C11 H11 110.3 . . ? C8 C11 H11 110.3 . . ? C20 C12 C13 110.2(2) . . ? C20 C12 C11 109.6(2) . . ? C13 C12 C11 118.7(2) . . ? C20 C12 C7 112.8(2) . . ? C13 C12 C7 117.9(2) . . ? C11 C12 C7 85.7(2) . . ? O4 C13 O5 126.4(3) . . ? O4 C13 C12 116.6(3) . . ? O5 C13 C12 117.1(2) . . ? O3 C14 N2 121.8(3) . . ? O3 C14 C11 122.6(3) . . ? N2 C14 C11 115.7(3) . . ? C16 C15 C20 120.8(3) . . ? C16 C15 N2 118.0(3) . . ? C20 C15 N2 121.2(3) . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 120.0(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 122.3(3) . . ? C18 C19 H19 118.8 . . ? C20 C19 H19 118.8 . . ? C19 C20 C15 117.2(3) . . ? C19 C20 C12 122.4(3) . . ? C15 C20 C12 120.3(3) . . ? N3 C21 C22 123.4(3) . . ? N3 C21 H21 118.3 . . ? C22 C21 H21 118.3 . . ? C23 C22 C21 120.6(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 116.6(3) . . ? C22 C23 C26 118.8(3) . . ? C24 C23 C26 124.6(3) . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? N3 C25 C24 123.3(3) . . ? N3 C25 H25 118.3 . . ? C24 C25 H25 118.3 . . ? C27 C26 C23 120.8(3) . . ? C27 C26 H26A 107.1 . . ? C23 C26 H26A 107.1 . . ? C27 C26 H26B 107.1 . . ? C23 C26 H26B 107.1 . . ? H26A C26 H26B 106.8 . . ? C26 C27 C28 111.4(3) . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C32 C28 C29 116.0(3) . . ? C32 C28 C27 121.9(4) . . ? C29 C28 C27 122.0(4) . . ? C30 C29 C28 119.7(4) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? N4 C30 C29 124.6(4) . . ? N4 C30 H30 117.7 . . ? C29 C30 H30 117.7 . . ? N4 C31 C32 124.0(3) . . ? N4 C31 H31 118.0 . . ? C32 C31 H31 118.0 . . ? C28 C32 C31 120.5(3) . . ? C28 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? O7 Mn1 O6 99.56(8) 7_657 . ? O7 Mn1 O9 157.19(9) 7_657 . ? O6 Mn1 O9 101.69(9) . . ? O7 Mn1 O8 76.42(8) 7_657 . ? O6 Mn1 O8 174.47(8) . . ? O9 Mn1 O8 82.88(9) . . ? O7 Mn1 N4 97.56(9) 7_657 3 ? O6 Mn1 N4 83.86(9) . 3 ? O9 Mn1 N4 92.89(9) . 3 ? O8 Mn1 N4 92.84(9) . 3 ? O7 Mn1 N3 92.45(8) 7_657 . ? O6 Mn1 N3 84.43(8) . . ? O9 Mn1 N3 81.48(8) . . ? O8 Mn1 N3 99.44(9) . . ? N4 Mn1 N3 165.70(9) 3 . ? C9 N1 C5 124.5(3) . . ? C9 N1 H1A 117.8 . . ? C5 N1 H1A 117.8 . . ? C14 N2 C15 125.4(2) . . ? C14 N2 H2A 117.3 . . ? C15 N2 H2A 117.3 . . ? C21 N3 C25 116.5(3) . . ? C21 N3 Mn1 119.2(2) . . ? C25 N3 Mn1 124.3(2) . . ? C30 N4 C31 115.2(3) . . ? C30 N4 Mn1 124.3(2) . 3_445 ? C31 N4 Mn1 120.2(2) . 3_445 ? C10 O6 Mn1 145.83(19) . . ? C10 O7 Mn1 148.23(19) . 7_657 ? Mn1 O8 H8A 127.3 . . ? Mn1 O8 H8B 120.0 . . ? H8A O8 H8B 112.3 . . ? Mn1 O9 H9B 122.3 . . ? Mn1 O9 H9A 130.5 . . ? H9B O9 H9A 106.8 . . ? H11A O11 H11B 107.7 . . ? O12 O12 H12A 61.3 2_655 . ? O12 O12 H12B 153.0 2_655 . ? H12A O12 H12B 102.4 . . ? H13A O13 H13B 110.9 . . ? H14B O14 H14A 104.9 . . ? H15A O15 H15B 111.9 . . ? 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 C6 C1 C2 C3 -1.5(5) . . . . ? C1 C2 C3 C4 0.8(6) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C3 C4 C5 N1 -179.8(3) . . . . ? C2 C1 C6 C5 1.2(5) . . . . ? C2 C1 C6 C7 179.0(3) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? N1 C5 C6 C1 179.2(3) . . . . ? C4 C5 C6 C7 -178.2(3) . . . . ? N1 C5 C6 C7 1.2(4) . . . . ? C1 C6 C7 C10 -72.2(4) . . . . ? C5 C6 C7 C10 105.7(3) . . . . ? C1 C6 C7 C8 157.6(3) . . . . ? C5 C6 C7 C8 -24.6(4) . . . . ? C1 C6 C7 C12 62.4(4) . . . . ? C5 C6 C7 C12 -119.7(3) . . . . ? C6 C7 C8 C9 35.5(3) . . . . ? C10 C7 C8 C9 -92.2(3) . . . . ? C12 C7 C8 C9 149.6(3) . . . . ? C6 C7 C8 C11 -88.2(2) . . . . ? C10 C7 C8 C11 144.2(2) . . . . ? C12 C7 C8 C11 25.9(2) . . . . ? C7 C8 C9 O1 157.9(3) . . . . ? C11 C8 C9 O1 -96.3(4) . . . . ? C7 C8 C9 N1 -22.2(4) . . . . ? C11 C8 C9 N1 83.7(3) . . . . ? C6 C7 C10 O6 -124.9(3) . . . . ? C8 C7 C10 O6 1.9(4) . . . . ? C12 C7 C10 O6 102.0(3) . . . . ? C6 C7 C10 O7 54.3(3) . . . . ? C8 C7 C10 O7 -178.9(2) . . . . ? C12 C7 C10 O7 -78.8(3) . . . . ? C9 C8 C11 C14 87.1(3) . . . . ? C7 C8 C11 C14 -149.8(3) . . . . ? C9 C8 C11 C12 -150.0(3) . . . . ? C7 C8 C11 C12 -26.9(2) . . . . ? C14 C11 C12 C20 32.2(4) . . . . ? C8 C11 C12 C20 -87.0(2) . . . . ? C14 C11 C12 C13 -95.5(3) . . . . ? C8 C11 C12 C13 145.3(3) . . . . ? C14 C11 C12 C7 144.9(3) . . . . ? C8 C11 C12 C7 25.77(19) . . . . ? C6 C7 C12 C20 -166.6(2) . . . . ? C10 C7 C12 C20 -34.5(3) . . . . ? C8 C7 C12 C20 83.2(2) . . . . ? C6 C7 C12 C13 -36.3(3) . . . . ? C10 C7 C12 C13 95.7(3) . . . . ? C8 C7 C12 C13 -146.5(2) . . . . ? C6 C7 C12 C11 84.0(3) . . . . ? C10 C7 C12 C11 -144.0(2) . . . . ? C8 C7 C12 C11 -26.2(2) . . . . ? C20 C12 C13 O4 -118.5(3) . . . . ? C11 C12 C13 O4 9.0(4) . . . . ? C7 C12 C13 O4 110.0(3) . . . . ? C20 C12 C13 O5 62.1(3) . . . . ? C11 C12 C13 O5 -170.5(3) . . . . ? C7 C12 C13 O5 -69.4(3) . . . . ? C12 C11 C14 O3 154.4(3) . . . . ? C8 C11 C14 O3 -101.9(3) . . . . ? C12 C11 C14 N2 -25.4(4) . . . . ? C8 C11 C14 N2 78.2(3) . . . . ? C20 C15 C16 C17 1.3(5) . . . . ? N2 C15 C16 C17 -176.8(3) . . . . ? C15 C16 C17 C18 0.1(5) . . . . ? C16 C17 C18 C19 -1.2(5) . . . . ? C17 C18 C19 C20 0.8(5) . . . . ? C18 C19 C20 C15 0.6(5) . . . . ? C18 C19 C20 C12 176.9(3) . . . . ? C16 C15 C20 C19 -1.6(5) . . . . ? N2 C15 C20 C19 176.4(3) . . . . ? C16 C15 C20 C12 -178.1(3) . . . . ? N2 C15 C20 C12 0.0(4) . . . . ? C13 C12 C20 C19 -63.2(3) . . . . ? C11 C12 C20 C19 164.5(3) . . . . ? C7 C12 C20 C19 70.9(3) . . . . ? C13 C12 C20 C15 113.1(3) . . . . ? C11 C12 C20 C15 -19.3(4) . . . . ? C7 C12 C20 C15 -112.9(3) . . . . ? N3 C21 C22 C23 0.9(6) . . . . ? C21 C22 C23 C24 0.0(6) . . . . ? C21 C22 C23 C26 -179.5(4) . . . . ? C22 C23 C24 C25 -0.7(5) . . . . ? C26 C23 C24 C25 178.8(4) . . . . ? C23 C24 C25 N3 0.5(6) . . . . ? C22 C23 C26 C27 -173.7(5) . . . . ? C24 C23 C26 C27 6.8(8) . . . . ? C23 C26 C27 C28 179.5(4) . . . . ? C26 C27 C28 C32 84.5(6) . . . . ? C26 C27 C28 C29 -91.2(5) . . . . ? C32 C28 C29 C30 1.3(7) . . . . ? C27 C28 C29 C30 177.2(4) . . . . ? C28 C29 C30 N4 -2.6(8) . . . . ? C29 C28 C32 C31 0.2(6) . . . . ? C27 C28 C32 C31 -175.7(3) . . . . ? N4 C31 C32 C28 -0.6(5) . . . . ? O1 C9 N1 C5 175.1(3) . . . . ? C8 C9 N1 C5 -4.9(4) . . . . ? C4 C5 N1 C9 -164.6(3) . . . . ? C6 C5 N1 C9 16.0(4) . . . . ? O3 C14 N2 C15 -176.8(3) . . . . ? C11 C14 N2 C15 3.0(4) . . . . ? C16 C15 N2 C14 -172.0(3) . . . . ? C20 C15 N2 C14 9.9(5) . . . . ? C22 C21 N3 C25 -1.1(5) . . . . ? C22 C21 N3 Mn1 -178.6(3) . . . . ? C24 C25 N3 C21 0.3(5) . . . . ? C24 C25 N3 Mn1 177.7(3) . . . . ? O7 Mn1 N3 C21 -55.0(2) 7_657 . . . ? O6 Mn1 N3 C21 -154.4(2) . . . . ? O9 Mn1 N3 C21 102.9(2) . . . . ? O8 Mn1 N3 C21 21.7(2) . . . . ? N4 Mn1 N3 C21 170.5(3) 3 . . . ? O7 Mn1 N3 C25 127.7(3) 7_657 . . . ? O6 Mn1 N3 C25 28.3(3) . . . . ? O9 Mn1 N3 C25 -74.4(3) . . . . ? O8 Mn1 N3 C25 -155.6(3) . . . . ? N4 Mn1 N3 C25 -6.8(5) 3 . . . ? C29 C30 N4 C31 2.2(6) . . . . ? C29 C30 N4 Mn1 175.9(4) . . . 3_445 ? C32 C31 N4 C30 -0.6(5) . . . . ? C32 C31 N4 Mn1 -174.5(3) . . . 3_445 ? O7 C10 O6 Mn1 -61.0(5) . . . . ? C7 C10 O6 Mn1 118.1(3) . . . . ? O7 Mn1 O6 C10 66.5(3) 7_657 . . . ? O9 Mn1 O6 C10 -121.9(3) . . . . ? O8 Mn1 O6 C10 23.4(11) . . . . ? N4 Mn1 O6 C10 -30.2(3) 3 . . . ? N3 Mn1 O6 C10 158.0(4) . . . . ? O6 C10 O7 Mn1 -7.9(6) . . . 7_657 ? C7 C10 O7 Mn1 173.0(3) . . . 7_657 ? 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 O8 H8A O3 0.85 2.08 2.925(3) 169.7 6_556 O9 H9B O4 0.85 1.89 2.742(3) 176.7 6_556 N2 H2A O15 0.86 2.00 2.860(3) 173.1 5_656 N1 H1A O3 0.86 2.19 3.041(3) 169.4 5_757 O8 H8B O5 0.85 2.05 2.896(3) 174.6 7_657 O9 H9A O12 0.85 1.92 2.749(8) 165.8 3_546 O9 H9A O12 0.85 2.03 2.844(8) 159.8 4_646 O15 H15B O14 0.85 1.94 2.758(4) 161.0 . O15 H15A O5 0.85 1.88 2.695(3) 159.1 8_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.837 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.065 # Attachment '- 8.cif' data_8 _database_code_depnum_ccdc_archive 'CCDC 853366' #TrackingRef '- 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H44 Cd N5 O13' _chemical_formula_weight 891.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.461(5) _cell_length_b 12.371(6) _cell_length_c 16.497(8) _cell_angle_alpha 78.244(6) _cell_angle_beta 77.713(6) _cell_angle_gamma 74.766(6) _cell_volume 1987.8(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5119 _cell_measurement_theta_min 2.223 _cell_measurement_theta_max 27.737 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 918 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8262 _exptl_absorpt_correction_T_max 0.8756 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 10484 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7250 _reflns_number_gt 6493 _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^)+(0.0489P)^2^+0.8736P] 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 7250 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6115(3) 0.5911(3) 0.45419(18) 0.0416(7) Uani 1 1 d . . . C2 C 0.6901(4) 0.4857(3) 0.4357(2) 0.0546(8) Uani 1 1 d . . . H2 H 0.6696 0.4513 0.3965 0.065 Uiso 1 1 calc R . . C3 C 0.7973(4) 0.4339(3) 0.4758(2) 0.0668(10) Uani 1 1 d . . . H3 H 0.8496 0.3639 0.4636 0.080 Uiso 1 1 calc R . . C4 C 0.8288(4) 0.4843(4) 0.5342(3) 0.0708(11) Uani 1 1 d . . . H4 H 0.9018 0.4480 0.5611 0.085 Uiso 1 1 calc R . . C5 C 0.7533(4) 0.5867(3) 0.5524(2) 0.0605(9) Uani 1 1 d . . . H5 H 0.7759 0.6201 0.5914 0.073 Uiso 1 1 calc R . . C6 C 0.6417(3) 0.6429(3) 0.51329(18) 0.0439(7) Uani 1 1 d . . . C7 C 0.5556(3) 0.7488(3) 0.53119(19) 0.0450(7) Uani 1 1 d . . . C8 C 0.4494(3) 0.7970(3) 0.4912(2) 0.0489(8) Uani 1 1 d . . . H8 H 0.3931 0.8651 0.5047 0.059 Uiso 1 1 calc R . . C9 C 0.4214(3) 0.7452(3) 0.42804(19) 0.0440(7) Uani 1 1 d . . . C10 C 0.5858(4) 0.8089(3) 0.5942(3) 0.0642(10) Uani 1 1 d . . . C11 C 0.8086(3) 1.0205(3) 1.08617(18) 0.0445(7) Uani 1 1 d . . . C12 C 0.7309(3) 1.0034(3) 1.02863(18) 0.0453(7) Uani 1 1 d . . . H12 H 0.6532 1.0574 1.0181 0.054 Uiso 1 1 calc R . . C13 C 0.7686(3) 0.9110(3) 0.98992(17) 0.0422(7) Uani 1 1 d . . . C14 C 0.6793(3) 0.8900(3) 0.93584(19) 0.0433(7) Uani 1 1 d . . . C15 C 0.8899(3) 0.8276(3) 1.00315(19) 0.0470(7) Uani 1 1 d . . . C16 C 0.9682(3) 0.8465(3) 1.05607(18) 0.0464(7) Uani 1 1 d . . . C17 C 1.0880(3) 0.7699(3) 1.0696(2) 0.0615(9) Uani 1 1 d . . . H17 H 1.1397 0.7825 1.1047 0.074 Uiso 1 1 calc R . . C18 C 1.1294(4) 0.6754(4) 1.0308(3) 0.0793(12) Uani 1 1 d . . . H18 H 1.2099 0.6242 1.0395 0.095 Uiso 1 1 calc R . . C19 C 0.9357(4) 0.7301(3) 0.9653(2) 0.0641(10) Uani 1 1 d . . . H19 H 0.8853 0.7158 0.9302 0.077 Uiso 1 1 calc R . . C20 C 0.4289(3) 1.1196(3) 0.7919(2) 0.0471(7) Uani 1 1 d . . . H20 H 0.4859 1.1059 0.8309 0.057 Uiso 1 1 calc R . . C21 C 0.3238(3) 1.2144(3) 0.7924(2) 0.0477(7) Uani 1 1 d . . . H21 H 0.3105 1.2621 0.8318 0.057 Uiso 1 1 calc R . . C22 C 0.2378(3) 1.2383(2) 0.73422(19) 0.0423(7) Uani 1 1 d . . . C23 C 0.2622(3) 1.1635(3) 0.6792(2) 0.0516(8) Uani 1 1 d . . . H23 H 0.2072 1.1755 0.6392 0.062 Uiso 1 1 calc R . . C24 C 0.3678(3) 1.0710(3) 0.6830(2) 0.0489(8) Uani 1 1 d . . . H24 H 0.3818 1.0215 0.6448 0.059 Uiso 1 1 calc R . . C25 C 0.1197(3) 1.3392(3) 0.7301(2) 0.0502(8) Uani 1 1 d . . . H25A H 0.1218 1.3758 0.6721 0.060 Uiso 1 1 calc R . . H25B H 0.0376 1.3120 0.7476 0.060 Uiso 1 1 calc R . . C26 C 0.1146(3) 1.4264(3) 0.7830(2) 0.0552(8) Uani 1 1 d . . . H26A H 0.1996 1.4491 0.7691 0.066 Uiso 1 1 calc R . . H26B H 0.1036 1.3921 0.8417 0.066 Uiso 1 1 calc R . . C27 C 0.0023(3) 1.5306(3) 0.7712(2) 0.0466(7) Uani 1 1 d . . . C28 C 0.0255(3) 1.6377(3) 0.7563(2) 0.0539(8) Uani 1 1 d . . . H28 H 0.1124 1.6470 0.7509 0.065 Uiso 1 1 calc R . . C29 C -0.0785(3) 1.7304(3) 0.7495(2) 0.0519(8) Uani 1 1 d . . . H29 H -0.0591 1.8015 0.7399 0.062 Uiso 1 1 calc R . . C30 C -0.2299(3) 1.6230(3) 0.7688(2) 0.0503(8) Uani 1 1 d . . . H30 H -0.3179 1.6167 0.7735 0.060 Uiso 1 1 calc R . . C31 C -0.1304(3) 1.5252(3) 0.7758(3) 0.0586(9) Uani 1 1 d . . . H31 H -0.1519 1.4550 0.7838 0.070 Uiso 1 1 calc R . . C32 C 0.4215(4) 0.6496(4) 0.2179(2) 0.0710(11) Uani 1 1 d . . . H32 H 0.3704 0.7147 0.2392 0.085 Uiso 1 1 calc R . . C33 C 0.4370(4) 0.6494(3) 0.1323(2) 0.0613(9) Uani 1 1 d . . . H33 H 0.3985 0.7134 0.0974 0.074 Uiso 1 1 calc R . . C34 C 0.5101(4) 0.5533(3) 0.0997(2) 0.0540(8) Uani 1 1 d . . . C35 C 0.5256(4) 0.5472(3) 0.0081(2) 0.0634(10) Uani 1 1 d . . . H35A H 0.4777 0.6186 -0.0196 0.076 Uiso 1 1 calc R . . H35B H 0.6200 0.5373 -0.0165 0.076 Uiso 1 1 calc R . . C36 C 0.5681(4) 0.4614(3) 0.1556(2) 0.0632(10) Uani 1 1 d . . . H36 H 0.6197 0.3952 0.1363 0.076 Uiso 1 1 calc R . . C37 C 0.5475(4) 0.4704(3) 0.2398(2) 0.0651(10) Uani 1 1 d . . . H37 H 0.5864 0.4085 0.2761 0.078 Uiso 1 1 calc R . . C43 C 1.0540(4) 0.6552(4) 0.9792(3) 0.0797(12) Uani 1 1 d . . . H43 H 1.0833 0.5906 0.9536 0.096 Uiso 1 1 calc R . . Cd1 Cd 0.62110(2) 0.885109(16) 0.745305(13) 0.03727(9) Uani 1 1 d . . . N1 N 0.9242(2) 0.9413(2) 1.09485(15) 0.0470(6) Uani 1 1 d . . . H1 H 0.9738 0.9510 1.1270 0.056 Uiso 1 1 calc R . . N2 N 0.4522(2) 1.0471(2) 0.73805(16) 0.0410(6) Uani 1 1 d . . . N3 N -0.2061(2) 1.7259(2) 0.75559(15) 0.0402(5) Uani 1 1 d . . . N4 N 0.5039(3) 0.6450(2) 0.41414(15) 0.0447(6) Uani 1 1 d . . . H4A H 0.4883 0.6120 0.3774 0.054 Uiso 1 1 calc R . . N5 N 0.4759(3) 0.5619(3) 0.27169(18) 0.0645(8) Uani 1 1 d . . . O1 O 0.6944(2) 0.93426(18) 0.85980(12) 0.0461(5) Uani 1 1 d . . . O2 O 0.6009(3) 0.8298(3) 0.97154(15) 0.0707(8) Uani 1 1 d . . . O3 O 0.7733(2) 1.1014(2) 1.12651(14) 0.0561(6) Uani 1 1 d . . . O4 O 0.3282(2) 0.7891(2) 0.38728(15) 0.0593(6) Uani 1 1 d . . . O5 O 0.5173(3) 0.8088(2) 0.66274(17) 0.0741(8) Uani 1 1 d . . . O6 O 0.0890(3) 0.7797(3) 0.3418(2) 0.0925(10) Uani 1 1 d . . . O7 O 0.7690(3) 0.1790(3) 0.28060(19) 0.0870(9) Uani 1 1 d . . . O8 O 0.0652(4) 0.9207(4) 0.5975(3) 0.1246(14) Uani 1 1 d . . . O9 O 0.9318(4) 0.8617(4) 0.4896(2) 0.1223(13) Uani 1 1 d . . . O10 O 0.6801(4) 0.8552(4) 0.5724(3) 0.1375(17) Uani 1 1 d . . . H13A H 0.5119 0.7670 0.9022 0.165 Uiso 1 1 d R . . H13B H 0.4079 0.8250 0.8602 0.165 Uiso 1 1 d R . . H1O7 H 0.6846 0.1957 0.2990 0.165 Uiso 1 1 d R . . H2O7 H 0.7784 0.1663 0.2304 0.165 Uiso 1 1 d R . . H2O8 H 0.0560 0.9828 0.6176 0.165 Uiso 1 1 d R . . H1O9 H 0.8619 0.8420 0.4834 0.165 Uiso 1 1 d R . . H2O9 H 0.9839 0.7979 0.5094 0.165 Uiso 1 1 d R . . H12B H 0.7272 1.0554 0.6463 0.165 Uiso 1 1 d R . . H12A H 0.8487 0.9777 0.6568 0.165 Uiso 1 1 d R . . H6A H 0.1704 0.7629 0.3508 0.165 Uiso 1 1 d R . . H6B H 0.0340 0.8034 0.3840 0.165 Uiso 1 1 d R . . H11B H 0.9282 0.0777 0.7521 0.165 Uiso 1 1 d R . . H11A H 0.8560 0.0058 0.8165 0.165 Uiso 1 1 d R . . H1O8 H 0.1298 0.8738 0.6193 0.165 Uiso 1 1 d R . . O11 O 0.9011(4) 0.0549(4) 0.8017(2) 0.1213(15) Uani 1 1 d . . . O12 O 0.7707(2) 0.9910(2) 0.66647(16) 0.0632(6) Uani 1 1 d . . . O13 O 0.4901(2) 0.78963(18) 0.85326(13) 0.0483(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0456(17) 0.0398(16) 0.0380(15) -0.0037(12) -0.0080(13) -0.0084(14) C2 0.064(2) 0.0440(19) 0.0534(19) -0.0111(15) -0.0073(17) -0.0072(17) C3 0.064(2) 0.047(2) 0.075(3) -0.0044(18) -0.006(2) 0.0044(18) C4 0.060(2) 0.069(3) 0.076(3) 0.002(2) -0.026(2) -0.001(2) C5 0.058(2) 0.067(2) 0.057(2) -0.0065(17) -0.0229(17) -0.0065(19) C6 0.0447(17) 0.0487(18) 0.0379(15) -0.0050(13) -0.0100(13) -0.0092(14) C7 0.0479(17) 0.0516(19) 0.0399(16) -0.0122(14) -0.0101(13) -0.0128(15) C8 0.0506(18) 0.0454(18) 0.0532(19) -0.0183(15) -0.0120(15) -0.0047(15) C9 0.0494(18) 0.0411(17) 0.0444(17) -0.0035(13) -0.0174(14) -0.0106(14) C10 0.066(2) 0.064(2) 0.071(3) -0.031(2) -0.033(2) 0.002(2) C11 0.0407(16) 0.060(2) 0.0351(15) -0.0042(14) -0.0103(13) -0.0145(15) C12 0.0373(15) 0.057(2) 0.0419(16) -0.0067(14) -0.0159(13) -0.0050(14) C13 0.0369(15) 0.0569(19) 0.0331(14) -0.0058(13) -0.0117(12) -0.0077(14) C14 0.0357(15) 0.0496(18) 0.0439(17) -0.0112(14) -0.0144(13) 0.0002(14) C15 0.0409(16) 0.059(2) 0.0395(16) -0.0080(14) -0.0130(13) -0.0040(15) C16 0.0361(15) 0.062(2) 0.0385(16) -0.0014(14) -0.0120(13) -0.0075(15) C17 0.0449(19) 0.078(3) 0.058(2) 0.0015(19) -0.0225(16) -0.0053(18) C18 0.053(2) 0.084(3) 0.088(3) -0.012(2) -0.024(2) 0.016(2) C19 0.059(2) 0.072(3) 0.060(2) -0.0216(19) -0.0223(18) 0.0057(19) C20 0.0447(17) 0.0398(17) 0.0545(19) -0.0072(14) -0.0173(14) 0.0014(14) C21 0.0487(18) 0.0378(17) 0.0531(18) -0.0151(14) -0.0088(15) 0.0025(14) C22 0.0334(15) 0.0347(15) 0.0519(17) 0.0015(13) -0.0075(13) -0.0018(12) C23 0.0468(18) 0.0470(19) 0.059(2) -0.0076(15) -0.0241(15) 0.0050(15) C24 0.0477(18) 0.0378(17) 0.060(2) -0.0090(14) -0.0216(15) 0.0038(14) C25 0.0428(17) 0.0405(17) 0.064(2) -0.0096(15) -0.0160(15) 0.0022(14) C26 0.0432(18) 0.0462(19) 0.078(2) -0.0113(17) -0.0224(17) -0.0016(15) C27 0.0400(16) 0.0379(17) 0.0594(19) -0.0112(14) -0.0125(14) 0.0013(13) C28 0.0366(16) 0.0427(18) 0.080(2) -0.0125(16) -0.0072(16) -0.0041(14) C29 0.0451(18) 0.0323(16) 0.074(2) -0.0077(15) -0.0091(16) -0.0028(14) C30 0.0370(16) 0.0379(17) 0.075(2) -0.0080(15) -0.0167(15) -0.0023(13) C31 0.0469(19) 0.0291(16) 0.097(3) -0.0052(17) -0.0202(18) -0.0015(14) C32 0.079(3) 0.077(3) 0.064(2) -0.033(2) -0.014(2) -0.012(2) C33 0.071(2) 0.057(2) 0.060(2) -0.0191(17) -0.0233(18) -0.0049(19) C34 0.061(2) 0.057(2) 0.0495(18) -0.0132(16) -0.0125(16) -0.0170(17) C35 0.082(3) 0.060(2) 0.0511(19) -0.0155(16) -0.0109(18) -0.017(2) C36 0.085(3) 0.051(2) 0.060(2) -0.0187(17) -0.0212(19) -0.012(2) C37 0.088(3) 0.057(2) 0.060(2) -0.0067(18) -0.029(2) -0.023(2) C43 0.070(3) 0.077(3) 0.083(3) -0.027(2) -0.022(2) 0.018(2) Cd1 0.03504(13) 0.02955(13) 0.04657(14) -0.00820(9) -0.01711(9) 0.00362(8) N1 0.0397(14) 0.0648(18) 0.0404(14) -0.0048(12) -0.0190(11) -0.0118(13) N2 0.0390(13) 0.0320(13) 0.0487(14) -0.0037(11) -0.0130(11) 0.0001(11) N3 0.0398(13) 0.0322(13) 0.0454(14) -0.0084(10) -0.0103(11) 0.0012(10) N4 0.0571(16) 0.0423(14) 0.0409(13) -0.0098(11) -0.0169(12) -0.0129(13) N5 0.082(2) 0.074(2) 0.0496(17) -0.0199(16) -0.0163(16) -0.0276(19) O1 0.0530(13) 0.0521(13) 0.0380(11) -0.0066(9) -0.0201(9) -0.0107(10) O2 0.0722(17) 0.104(2) 0.0501(14) 0.0050(14) -0.0252(12) -0.0462(17) O3 0.0513(13) 0.0715(16) 0.0535(13) -0.0250(12) -0.0149(11) -0.0113(12) O4 0.0656(15) 0.0491(14) 0.0702(15) -0.0063(11) -0.0372(13) -0.0072(12) O5 0.0821(19) 0.0834(19) 0.0591(16) -0.0377(14) -0.0268(14) 0.0095(15) O6 0.088(2) 0.101(2) 0.102(2) 0.0003(19) -0.0486(18) -0.0325(19) O7 0.096(2) 0.105(2) 0.0782(19) -0.0216(17) -0.0264(17) -0.040(2) O8 0.126(3) 0.126(3) 0.131(3) 0.014(3) -0.062(3) -0.038(3) O9 0.122(3) 0.145(4) 0.109(3) -0.005(2) -0.026(2) -0.053(3) O10 0.131(3) 0.188(4) 0.149(4) -0.084(3) -0.014(3) -0.095(3) O11 0.131(3) 0.195(4) 0.077(2) 0.034(2) -0.063(2) -0.111(3) O12 0.0523(14) 0.0438(13) 0.0795(17) 0.0029(12) -0.0030(12) -0.0030(11) O13 0.0516(12) 0.0462(12) 0.0475(12) -0.0065(10) -0.0147(10) -0.0076(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.375(4) . ? C1 C6 1.398(4) . ? C1 C2 1.400(4) . ? C2 C3 1.367(5) . ? C2 H2 0.9300 . ? C3 C4 1.384(6) . ? C3 H3 0.9300 . ? C4 C5 1.358(5) . ? C4 H4 0.9300 . ? C5 C6 1.405(4) . ? C5 H5 0.9300 . ? C6 C7 1.428(4) . ? C7 C8 1.352(4) . ? C7 C10 1.521(4) . ? C8 C9 1.444(4) . ? C8 H8 0.9300 . ? C9 O4 1.244(4) . ? C9 N4 1.343(4) . ? C10 O5 1.202(5) . ? C10 O10 1.222(5) . ? C11 O3 1.247(4) . ? C11 N1 1.356(4) . ? C11 C12 1.451(4) . ? C12 C13 1.350(4) . ? C12 H12 0.9300 . ? C13 C15 1.435(4) . ? C13 C14 1.520(4) . ? C14 O2 1.229(4) . ? C14 O1 1.257(4) . ? C15 C19 1.397(5) . ? C15 C16 1.406(4) . ? C16 N1 1.376(4) . ? C16 C17 1.388(5) . ? C17 C18 1.374(6) . ? C17 H17 0.9300 . ? C18 C43 1.373(6) . ? C18 H18 0.9300 . ? C19 C43 1.368(5) . ? C19 H19 0.9300 . ? C20 N2 1.331(4) . ? C20 C21 1.380(4) . ? C20 H20 0.9300 . ? C21 C22 1.389(4) . ? C21 H21 0.9300 . ? C22 C23 1.366(4) . ? C22 C25 1.510(4) . ? C23 C24 1.367(4) . ? C23 H23 0.9300 . ? C24 N2 1.337(4) . ? C24 H24 0.9300 . ? C25 C26 1.503(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.510(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.373(4) . ? C27 C31 1.393(4) . ? C28 C29 1.361(4) . ? C28 H28 0.9300 . ? C29 N3 1.332(4) . ? C29 H29 0.9300 . ? C30 N3 1.327(4) . ? C30 C31 1.376(4) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 N5 1.336(5) . ? C32 C33 1.388(5) . ? C32 H32 0.9300 . ? C33 C34 1.376(5) . ? C33 H33 0.9300 . ? C34 C36 1.399(5) . ? C34 C35 1.501(5) . ? C35 C35 1.497(7) 2_665 ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.383(5) . ? C36 H36 0.9300 . ? C37 N5 1.322(5) . ? C37 H37 0.9300 . ? C43 H43 0.9300 . ? Cd1 N2 2.299(2) . ? Cd1 N3 2.301(2) 1_645 ? Cd1 O12 2.318(2) . ? Cd1 O13 2.324(2) . ? Cd1 O5 2.370(3) . ? Cd1 O1 2.420(2) . ? N1 H1 0.8600 . ? N3 Cd1 2.301(2) 1_465 ? N4 H4A 0.8600 . ? O6 H6A 0.8594 . ? O6 H6B 0.8512 . ? O7 H1O7 0.8540 . ? O7 H2O7 0.8546 . ? O8 H2O8 0.8740 . ? O8 H1O8 0.8579 . ? O9 H1O9 0.8600 . ? O9 H2O9 0.8784 . ? O11 H11B 0.8237 . ? O11 H11A 0.8325 . ? O12 H12B 0.8477 . ? O12 H12A 0.7766 . ? O13 H13A 0.8568 . ? O13 H13B 0.8510 . ? 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 N4 C1 C6 119.2(3) . . ? N4 C1 C2 120.3(3) . . ? C6 C1 C2 120.5(3) . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.0(3) . . ? C1 C6 C7 117.8(3) . . ? C5 C6 C7 124.2(3) . . ? C8 C7 C6 120.5(3) . . ? C8 C7 C10 119.9(3) . . ? C6 C7 C10 119.6(3) . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? O4 C9 N4 120.6(3) . . ? O4 C9 C8 123.5(3) . . ? N4 C9 C8 115.9(3) . . ? O5 C10 O10 123.0(4) . . ? O5 C10 C7 119.3(4) . . ? O10 C10 C7 117.7(4) . . ? O3 C11 N1 120.7(3) . . ? O3 C11 C12 123.5(3) . . ? N1 C11 C12 115.8(3) . . ? C13 C12 C11 121.7(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C15 120.4(3) . . ? C12 C13 C14 120.6(3) . . ? C15 C13 C14 118.9(3) . . ? O2 C14 O1 127.0(3) . . ? O2 C14 C13 115.9(3) . . ? O1 C14 C13 117.1(3) . . ? C19 C15 C16 118.2(3) . . ? C19 C15 C13 123.8(3) . . ? C16 C15 C13 118.0(3) . . ? N1 C16 C17 120.4(3) . . ? N1 C16 C15 119.2(3) . . ? C17 C16 C15 120.4(3) . . ? C18 C17 C16 119.4(3) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C43 C18 C17 121.1(4) . . ? C43 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C43 C19 C15 120.8(3) . . ? C43 C19 H19 119.6 . . ? C15 C19 H19 119.6 . . ? N2 C20 C21 122.9(3) . . ? N2 C20 H20 118.6 . . ? C21 C20 H20 118.6 . . ? C20 C21 C22 120.0(3) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 116.8(3) . . ? C23 C22 C25 119.3(3) . . ? C21 C22 C25 124.0(3) . . ? C22 C23 C24 119.9(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? N2 C24 C23 124.2(3) . . ? N2 C24 H24 117.9 . . ? C23 C24 H24 117.9 . . ? C26 C25 C22 115.1(3) . . ? C26 C25 H25A 108.5 . . ? C22 C25 H25A 108.5 . . ? C26 C25 H25B 108.5 . . ? C22 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C25 C26 C27 113.5(3) . . ? C25 C26 H26A 108.9 . . ? C27 C26 H26A 108.9 . . ? C25 C26 H26B 108.9 . . ? C27 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? C28 C27 C31 115.8(3) . . ? C28 C27 C26 121.4(3) . . ? C31 C27 C26 122.9(3) . . ? C29 C28 C27 120.2(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? N3 C29 C28 124.4(3) . . ? N3 C29 H29 117.8 . . ? C28 C29 H29 117.8 . . ? N3 C30 C31 123.1(3) . . ? N3 C30 H30 118.5 . . ? C31 C30 H30 118.5 . . ? C30 C31 C27 120.4(3) . . ? C30 C31 H31 119.8 . . ? C27 C31 H31 119.8 . . ? N5 C32 C33 123.8(4) . . ? N5 C32 H32 118.1 . . ? C33 C32 H32 118.1 . . ? C34 C33 C32 119.1(4) . . ? C34 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? C33 C34 C36 117.4(3) . . ? C33 C34 C35 121.2(3) . . ? C36 C34 C35 121.4(3) . . ? C35 C35 C34 113.4(4) 2_665 . ? C35 C35 H35A 108.9 2_665 . ? C34 C35 H35A 108.9 . . ? C35 C35 H35B 108.9 2_665 . ? C34 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C34 119.1(3) . . ? C37 C36 H36 120.4 . . ? C34 C36 H36 120.4 . . ? N5 C37 C36 123.9(4) . . ? N5 C37 H37 118.1 . . ? C36 C37 H37 118.1 . . ? C19 C43 C18 120.1(4) . . ? C19 C43 H43 119.9 . . ? C18 C43 H43 119.9 . . ? N2 Cd1 N3 177.82(8) . 1_645 ? N2 Cd1 O12 88.72(9) . . ? N3 Cd1 O12 90.39(9) 1_645 . ? N2 Cd1 O13 92.27(9) . . ? N3 Cd1 O13 88.07(9) 1_645 . ? O12 Cd1 O13 165.08(8) . . ? N2 Cd1 O5 89.34(9) . . ? N3 Cd1 O5 92.84(9) 1_645 . ? O12 Cd1 O5 113.52(10) . . ? O13 Cd1 O5 81.38(10) . . ? N2 Cd1 O1 92.21(8) . . ? N3 Cd1 O1 85.69(8) 1_645 . ? O12 Cd1 O1 81.66(9) . . ? O13 Cd1 O1 83.43(8) . . ? O5 Cd1 O1 164.78(9) . . ? C11 N1 C16 124.8(3) . . ? C11 N1 H1 117.6 . . ? C16 N1 H1 117.6 . . ? C20 N2 C24 116.2(3) . . ? C20 N2 Cd1 121.3(2) . . ? C24 N2 Cd1 122.3(2) . . ? C30 N3 C29 116.1(3) . . ? C30 N3 Cd1 120.8(2) . 1_465 ? C29 N3 Cd1 123.1(2) . 1_465 ? C9 N4 C1 125.0(3) . . ? C9 N4 H4A 117.5 . . ? C1 N4 H4A 117.5 . . ? C37 N5 C32 116.7(3) . . ? C14 O1 Cd1 127.8(2) . . ? C10 O5 Cd1 107.4(3) . . ? H6A O6 H6B 111.2 . . ? H1O7 O7 H2O7 106.9 . . ? H2O8 O8 H1O8 104.0 . . ? H1O9 O9 H2O9 104.3 . . ? H11B O11 H11A 123.0 . . ? Cd1 O12 H12B 109.4 . . ? Cd1 O12 H12A 132.0 . . ? H12B O12 H12A 118.7 . . ? Cd1 O13 H13A 121.5 . . ? Cd1 O13 H13B 112.2 . . ? H13A O13 H13B 107.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C3 179.5(3) . . . . ? C6 C1 C2 C3 -0.3(5) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 C6 0.6(6) . . . . ? N4 C1 C6 C5 -179.2(3) . . . . ? C2 C1 C6 C5 0.6(5) . . . . ? N4 C1 C6 C7 2.0(4) . . . . ? C2 C1 C6 C7 -178.2(3) . . . . ? C4 C5 C6 C1 -0.8(5) . . . . ? C4 C5 C6 C7 178.0(3) . . . . ? C1 C6 C7 C8 -0.6(5) . . . . ? C5 C6 C7 C8 -179.4(3) . . . . ? C1 C6 C7 C10 -179.2(3) . . . . ? C5 C6 C7 C10 2.0(5) . . . . ? C6 C7 C8 C9 -1.6(5) . . . . ? C10 C7 C8 C9 177.0(3) . . . . ? C7 C8 C9 O4 -176.9(3) . . . . ? C7 C8 C9 N4 2.4(5) . . . . ? C8 C7 C10 O5 75.5(5) . . . . ? C6 C7 C10 O5 -105.9(4) . . . . ? C8 C7 C10 O10 -104.6(5) . . . . ? C6 C7 C10 O10 73.9(5) . . . . ? O3 C11 C12 C13 -176.0(3) . . . . ? N1 C11 C12 C13 3.4(4) . . . . ? C11 C12 C13 C15 -1.6(5) . . . . ? C11 C12 C13 C14 174.7(3) . . . . ? C12 C13 C14 O2 -93.3(4) . . . . ? C15 C13 C14 O2 83.1(4) . . . . ? C12 C13 C14 O1 87.7(4) . . . . ? C15 C13 C14 O1 -95.9(4) . . . . ? C12 C13 C15 C19 -179.8(3) . . . . ? C14 C13 C15 C19 3.8(5) . . . . ? C12 C13 C15 C16 -1.1(5) . . . . ? C14 C13 C15 C16 -177.5(3) . . . . ? C19 C15 C16 N1 -179.2(3) . . . . ? C13 C15 C16 N1 2.0(4) . . . . ? C19 C15 C16 C17 0.2(5) . . . . ? C13 C15 C16 C17 -178.6(3) . . . . ? N1 C16 C17 C18 179.5(3) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C16 C17 C18 C43 -0.4(6) . . . . ? C16 C15 C19 C43 -0.2(6) . . . . ? C13 C15 C19 C43 178.5(4) . . . . ? N2 C20 C21 C22 -0.9(5) . . . . ? C20 C21 C22 C23 1.0(5) . . . . ? C20 C21 C22 C25 179.6(3) . . . . ? C21 C22 C23 C24 -0.4(5) . . . . ? C25 C22 C23 C24 -179.1(3) . . . . ? C22 C23 C24 N2 -0.1(5) . . . . ? C23 C22 C25 C26 -170.2(3) . . . . ? C21 C22 C25 C26 11.2(5) . . . . ? C22 C25 C26 C27 174.8(3) . . . . ? C25 C26 C27 C28 -130.7(4) . . . . ? C25 C26 C27 C31 50.3(5) . . . . ? C31 C27 C28 C29 1.9(5) . . . . ? C26 C27 C28 C29 -177.2(3) . . . . ? C27 C28 C29 N3 -0.5(6) . . . . ? N3 C30 C31 C27 1.5(6) . . . . ? C28 C27 C31 C30 -2.3(5) . . . . ? C26 C27 C31 C30 176.7(3) . . . . ? N5 C32 C33 C34 1.3(6) . . . . ? C32 C33 C34 C36 -1.6(5) . . . . ? C32 C33 C34 C35 177.7(4) . . . . ? C33 C34 C35 C35 -121.3(5) . . . 2_665 ? C36 C34 C35 C35 58.0(6) . . . 2_665 ? C33 C34 C36 C37 1.2(5) . . . . ? C35 C34 C36 C37 -178.2(3) . . . . ? C34 C36 C37 N5 -0.3(6) . . . . ? C15 C19 C43 C18 -0.1(7) . . . . ? C17 C18 C43 C19 0.4(7) . . . . ? O3 C11 N1 C16 176.9(3) . . . . ? C12 C11 N1 C16 -2.6(4) . . . . ? C17 C16 N1 C11 -179.5(3) . . . . ? C15 C16 N1 C11 -0.1(5) . . . . ? C21 C20 N2 C24 0.4(4) . . . . ? C21 C20 N2 Cd1 -176.3(2) . . . . ? C23 C24 N2 C20 0.2(5) . . . . ? C23 C24 N2 Cd1 176.8(3) . . . . ? N3 Cd1 N2 C20 -18(2) 1_645 . . . ? O12 Cd1 N2 C20 -84.6(2) . . . . ? O13 Cd1 N2 C20 80.5(2) . . . . ? O5 Cd1 N2 C20 161.9(2) . . . . ? O1 Cd1 N2 C20 -3.0(2) . . . . ? N3 Cd1 N2 C24 165(2) 1_645 . . . ? O12 Cd1 N2 C24 99.0(2) . . . . ? O13 Cd1 N2 C24 -95.9(2) . . . . ? O5 Cd1 N2 C24 -14.5(2) . . . . ? O1 Cd1 N2 C24 -179.4(2) . . . . ? C31 C30 N3 C29 -0.1(5) . . . . ? C31 C30 N3 Cd1 -179.7(3) . . . 1_465 ? C28 C29 N3 C30 -0.4(5) . . . . ? C28 C29 N3 Cd1 179.2(3) . . . 1_465 ? O4 C9 N4 C1 178.3(3) . . . . ? C8 C9 N4 C1 -1.0(4) . . . . ? C6 C1 N4 C9 -1.1(4) . . . . ? C2 C1 N4 C9 179.1(3) . . . . ? C36 C37 N5 C32 -0.2(6) . . . . ? C33 C32 N5 C37 -0.3(6) . . . . ? O2 C14 O1 Cd1 -16.6(5) . . . . ? C13 C14 O1 Cd1 162.27(19) . . . . ? N2 Cd1 O1 C14 107.1(3) . . . . ? N3 Cd1 O1 C14 -73.5(3) 1_645 . . . ? O12 Cd1 O1 C14 -164.5(3) . . . . ? O13 Cd1 O1 C14 15.1(2) . . . . ? O5 Cd1 O1 C14 11.5(4) . . . . ? O10 C10 O5 Cd1 -8.7(5) . . . . ? C7 C10 O5 Cd1 171.1(3) . . . . ? N2 Cd1 O5 C10 108.0(3) . . . . ? N3 Cd1 O5 C10 -71.9(3) 1_645 . . . ? O12 Cd1 O5 C10 19.7(3) . . . . ? O13 Cd1 O5 C10 -159.6(3) . . . . ? O1 Cd1 O5 C10 -156.0(3) . . . . ? 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 N1 H1 O11 0.86 1.92 2.768(4) 169.9 2_767 N4 H4A N5 0.86 2.01 2.847(4) 165.8 . O13 H13A O2 0.86 1.99 2.657(3) 133.4 . O13 H13B O3 0.85 1.86 2.713(3) 177.9 2_677 O7 H1O7 O5 0.85 2.08 2.914(5) 163.9 2_666 O9 H1O9 O10 0.86 2.13 2.709(6) 124.1 . O7 H2O7 O3 0.85 2.05 2.882(4) 164.1 1_544 O8 H2O8 O9 0.87 2.34 2.787(6) 111.6 2_676 O12 H12B O4 0.85 1.86 2.681(3) 162.5 2_676 O12 H12A O8 0.78 2.25 3.008(5) 163.6 1_655 O6 H6A O4 0.86 1.99 2.797(4) 155.2 . O6 H6B O9 0.85 2.00 2.846(6) 170.4 1_455 O11 H11B O6 0.82 2.09 2.799(5) 143.5 2_666 O11 H11A O1 0.83 2.04 2.837(4) 160.1 1_545 O8 H1O8 O7 0.86 2.05 2.816(5) 147.7 2_666 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.662 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.065 # Attachment '- 9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 853367' #TrackingRef '- 9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 N6 O16 Zn' _chemical_formula_weight 806.05 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 6.904(5) _cell_length_b 10.602(7) _cell_length_c 13.212(9) _cell_angle_alpha 99.906(9) _cell_angle_beta 104.443(9) _cell_angle_gamma 105.949(9) _cell_volume 869.9(10) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1885 _cell_measurement_theta_min 2.959 _cell_measurement_theta_max 27.971 _exptl_crystal_description bar _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7863 _exptl_absorpt_correction_T_max 0.9395 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 4558 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3169 _reflns_number_gt 2847 _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^)+(0.0469P)^2^+0.3435P] 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 3169 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4740(4) 0.4896(2) 0.6511(2) 0.0322(5) Uani 1 1 d . . . C2 C 0.4440(4) 0.4720(2) 0.7530(2) 0.0320(5) Uani 1 1 d . . . H2 H 0.5611 0.5048 0.8151 0.038 Uiso 1 1 calc R . . C3 C 0.2520(4) 0.4096(2) 0.76073(19) 0.0286(5) Uani 1 1 d . . . C4 C 0.2298(4) 0.3991(2) 0.8710(2) 0.0312(5) Uani 1 1 d . . . C5 C 0.0687(4) 0.3538(2) 0.66498(19) 0.0304(5) Uani 1 1 d . . . C6 C -0.1368(4) 0.2840(3) 0.6641(2) 0.0415(6) Uani 1 1 d . . . H6 H -0.1615 0.2729 0.7286 0.050 Uiso 1 1 calc R . . C7 C -0.3007(4) 0.2324(3) 0.5694(2) 0.0524(8) Uani 1 1 d . . . H7 H -0.4361 0.1863 0.5698 0.063 Uiso 1 1 calc R . . C8 C -0.2670(4) 0.2482(3) 0.4724(2) 0.0507(7) Uani 1 1 d . . . H8 H -0.3802 0.2129 0.4085 0.061 Uiso 1 1 calc R . . C9 C -0.0693(4) 0.3149(3) 0.4697(2) 0.0407(6) Uani 1 1 d . . . H9 H -0.0474 0.3256 0.4045 0.049 Uiso 1 1 calc R . . C10 C 0.0991(4) 0.3667(2) 0.5659(2) 0.0319(5) Uani 1 1 d . . . C11 C 0.2074(4) 0.0464(2) 0.82704(19) 0.0296(5) Uani 1 1 d . . . H11 H 0.3278 0.0814 0.8876 0.036 Uiso 1 1 calc R . . C12 C 0.2305(4) 0.0576(3) 0.72853(19) 0.0335(6) Uani 1 1 d . . . H12 H 0.3631 0.0995 0.7227 0.040 Uiso 1 1 calc R . . C13 C 0.0544(4) 0.0059(3) 0.63889(19) 0.0327(6) Uani 1 1 d . . . C14 C -0.1377(4) -0.0599(3) 0.6506(2) 0.0544(9) Uani 1 1 d . . . H14 H -0.2588 -0.1000 0.5907 0.065 Uiso 1 1 calc R . . C15 C -0.1466(4) -0.0652(3) 0.7520(2) 0.0485(8) Uani 1 1 d . . . H15 H -0.2770 -0.1081 0.7597 0.058 Uiso 1 1 calc R . . N1 N 0.0229(3) -0.0116(2) 0.84059(15) 0.0281(4) Uani 1 1 d . . . N2 N 0.2993(3) 0.4331(2) 0.56349(16) 0.0343(5) Uani 1 1 d . . . H2C H 0.3140 0.4390 0.5015 0.041 Uiso 1 1 calc R . . N3 N 0.0830(3) 0.0251(2) 0.53845(16) 0.0369(5) Uani 1 1 d . . . O1 O 0.1726(3) 0.21182(16) 1.05251(13) 0.0317(4) Uani 1 1 d . . . H1A H 0.2218 0.2610 1.0142 0.048 Uiso 1 1 d R . . H2A H 0.4103 0.0138 1.0837 0.048 Uiso 1 1 d R . . O2 O 0.2864(3) -0.03856(17) 1.04451(14) 0.0361(4) Uani 1 1 d . . . H1B H 0.1040 0.2583 1.0793 0.054 Uiso 1 1 d R . . H2B H 0.2884 -0.1150 1.0552 0.054 Uiso 1 1 d R . . O3 O 0.3413(3) 0.34335(19) 0.92369(14) 0.0403(4) Uani 1 1 d . . . O4 O 0.1018(3) 0.44717(19) 0.90063(15) 0.0425(5) Uani 1 1 d . . . O5 O 0.6473(3) 0.5523(2) 0.64162(14) 0.0432(5) Uani 1 1 d . . . O6 O 0.6997(3) 0.27380(19) 0.90527(18) 0.0489(5) Uani 1 1 d . . . O7 O 0.9994(3) 0.64949(18) 0.82272(14) 0.0386(4) Uani 1 1 d . . . O8 O 0.4079(3) 0.7992(2) 0.82241(18) 0.0515(5) Uani 1 1 d . . . Zn1 Zn 0.0000 0.0000 1.0000 0.02457(13) Uani 1 2 d S . . H7A H 0.8997 0.6187 0.7630 0.037 Uiso 1 1 d R . . H6B H 0.6006 0.3055 0.9077 0.037 Uiso 1 1 d R . . H8B H 0.2798 0.7647 0.8199 0.037 Uiso 1 1 d R . . H6A H 0.8221 0.3315 0.9192 0.037 Uiso 1 1 d R . . H7B H 1.0299 0.5893 0.8523 0.037 Uiso 1 1 d R . . H8A H 0.4909 0.7589 0.8493 0.037 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0316(14) 0.0364(13) 0.0293(13) 0.0108(11) 0.0116(11) 0.0089(11) C2 0.0332(14) 0.0362(13) 0.0263(12) 0.0121(10) 0.0105(10) 0.0076(11) C3 0.0349(13) 0.0262(12) 0.0295(13) 0.0104(10) 0.0148(10) 0.0115(10) C4 0.0339(13) 0.0302(13) 0.0301(13) 0.0094(10) 0.0152(11) 0.0061(11) C5 0.0330(13) 0.0294(12) 0.0314(13) 0.0093(10) 0.0138(11) 0.0104(10) C6 0.0375(15) 0.0487(16) 0.0390(15) 0.0124(13) 0.0190(12) 0.0084(12) C7 0.0290(15) 0.070(2) 0.0471(18) 0.0122(15) 0.0113(13) 0.0011(14) C8 0.0326(15) 0.064(2) 0.0428(17) 0.0090(14) 0.0037(13) 0.0070(14) C9 0.0395(15) 0.0481(16) 0.0329(14) 0.0112(12) 0.0113(12) 0.0114(12) C10 0.0311(13) 0.0331(13) 0.0326(13) 0.0093(11) 0.0111(11) 0.0108(11) C11 0.0278(13) 0.0382(13) 0.0226(12) 0.0084(10) 0.0069(10) 0.0112(10) C12 0.0313(13) 0.0450(14) 0.0259(13) 0.0111(11) 0.0130(10) 0.0108(11) C13 0.0363(14) 0.0399(14) 0.0216(12) 0.0107(10) 0.0130(10) 0.0071(11) C14 0.0343(16) 0.086(2) 0.0201(13) 0.0139(14) 0.0022(11) -0.0089(15) C15 0.0302(14) 0.077(2) 0.0226(13) 0.0144(13) 0.0072(11) -0.0057(14) N1 0.0292(11) 0.0351(11) 0.0199(10) 0.0101(8) 0.0087(8) 0.0076(8) N2 0.0333(12) 0.0437(12) 0.0266(11) 0.0135(9) 0.0132(9) 0.0077(9) N3 0.0393(12) 0.0491(13) 0.0211(10) 0.0132(9) 0.0130(8) 0.0070(10) O1 0.0413(10) 0.0303(9) 0.0290(9) 0.0124(7) 0.0187(8) 0.0107(7) O2 0.0273(9) 0.0408(10) 0.0410(10) 0.0152(8) 0.0071(8) 0.0131(8) O3 0.0478(11) 0.0494(11) 0.0389(10) 0.0251(9) 0.0232(9) 0.0227(9) O4 0.0484(11) 0.0547(12) 0.0395(11) 0.0180(9) 0.0261(9) 0.0258(10) O5 0.0316(10) 0.0618(12) 0.0326(10) 0.0189(9) 0.0139(8) 0.0024(9) O6 0.0367(11) 0.0442(11) 0.0699(14) 0.0208(10) 0.0185(10) 0.0144(9) O7 0.0361(10) 0.0420(10) 0.0357(10) 0.0086(8) 0.0084(8) 0.0133(8) O8 0.0345(10) 0.0500(12) 0.0698(14) 0.0192(11) 0.0153(10) 0.0125(9) Zn1 0.0263(2) 0.0323(2) 0.0174(2) 0.00956(15) 0.00859(15) 0.00984(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O5 1.247(3) . ? C1 N2 1.350(3) . ? C1 C2 1.446(3) . ? C2 C3 1.347(3) . ? C2 H2 0.9300 . ? C3 C5 1.444(4) . ? C3 C4 1.522(3) . ? C4 O4 1.243(3) . ? C4 O3 1.246(3) . ? C5 C10 1.400(4) . ? C5 C6 1.405(4) . ? C6 C7 1.366(4) . ? C6 H6 0.9300 . ? C7 C8 1.388(4) . ? C7 H7 0.9300 . ? C8 C9 1.367(4) . ? C8 H8 0.9300 . ? C9 C10 1.393(4) . ? C9 H9 0.9300 . ? C10 N2 1.379(3) . ? C11 N1 1.325(3) . ? C11 C12 1.371(3) . ? C11 H11 0.9300 . ? C12 C13 1.369(4) . ? C12 H12 0.9300 . ? C13 C14 1.379(4) . ? C13 N3 1.429(3) . ? C14 C15 1.366(4) . ? C14 H14 0.9300 . ? C15 N1 1.336(3) . ? C15 H15 0.9300 . ? N1 Zn1 2.136(2) . ? N2 H2C 0.8600 . ? N3 N3 1.236(4) 2_556 ? O1 Zn1 2.127(2) . ? O1 H1A 0.8500 . ? O1 H1B 0.8628 . ? O2 Zn1 2.090(2) . ? O2 H2A 0.8527 . ? O2 H2B 0.8500 . ? O6 H6B 0.8458 . ? O6 H6A 0.8495 . ? O7 H7A 0.8485 . ? O7 H7B 0.8506 . ? O8 H8B 0.8494 . ? O8 H8A 0.8498 . ? Zn1 O2 2.090(2) 2_557 ? Zn1 O1 2.127(2) 2_557 ? Zn1 N1 2.136(2) 2_557 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 C1 N2 120.4(2) . . ? O5 C1 C2 124.0(2) . . ? N2 C1 C2 115.7(2) . . ? C3 C2 C1 122.1(2) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C5 120.1(2) . . ? C2 C3 C4 119.6(2) . . ? C5 C3 C4 120.3(2) . . ? O4 C4 O3 125.7(2) . . ? O4 C4 C3 117.1(2) . . ? O3 C4 C3 117.3(2) . . ? C10 C5 C6 117.8(2) . . ? C10 C5 C3 117.7(2) . . ? C6 C5 C3 124.4(2) . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.5(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.0(3) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? N2 C10 C9 119.3(2) . . ? N2 C10 C5 119.4(2) . . ? C9 C10 C5 121.3(2) . . ? N1 C11 C12 123.5(2) . . ? N1 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C13 C12 C11 118.7(2) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 118.7(2) . . ? C12 C13 N3 117.0(2) . . ? C14 C13 N3 124.2(2) . . ? C15 C14 C13 118.7(2) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N1 C15 C14 123.2(2) . . ? N1 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C11 N1 C15 117.2(2) . . ? C11 N1 Zn1 119.98(15) . . ? C15 N1 Zn1 122.57(17) . . ? C1 N2 C10 124.9(2) . . ? C1 N2 H2C 117.6 . . ? C10 N2 H2C 117.6 . . ? N3 N3 C13 113.0(3) 2_556 . ? Zn1 O1 H1A 126.2 . . ? Zn1 O1 H1B 112.4 . . ? H1A O1 H1B 101.0 . . ? Zn1 O2 H2A 130.7 . . ? Zn1 O2 H2B 120.6 . . ? H2A O2 H2B 101.9 . . ? H6B O6 H6A 116.4 . . ? H7A O7 H7B 114.8 . . ? H8B O8 H8A 115.0 . . ? O2 Zn1 O2 180.000(1) . 2_557 ? O2 Zn1 O1 90.84(8) . 2_557 ? O2 Zn1 O1 89.16(8) 2_557 2_557 ? O2 Zn1 O1 89.16(8) . . ? O2 Zn1 O1 90.84(8) 2_557 . ? O1 Zn1 O1 180.0 2_557 . ? O2 Zn1 N1 88.86(7) . . ? O2 Zn1 N1 91.14(7) 2_557 . ? O1 Zn1 N1 87.73(7) 2_557 . ? O1 Zn1 N1 92.27(7) . . ? O2 Zn1 N1 91.14(7) . 2_557 ? O2 Zn1 N1 88.86(7) 2_557 2_557 ? O1 Zn1 N1 92.27(7) 2_557 2_557 ? O1 Zn1 N1 87.73(7) . 2_557 ? N1 Zn1 N1 180.000(1) . 2_557 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 C1 C2 C3 176.5(2) . . . . ? N2 C1 C2 C3 -3.4(4) . . . . ? C1 C2 C3 C5 2.0(4) . . . . ? C1 C2 C3 C4 -177.7(2) . . . . ? C2 C3 C4 O4 123.3(3) . . . . ? C5 C3 C4 O4 -56.4(3) . . . . ? C2 C3 C4 O3 -56.6(3) . . . . ? C5 C3 C4 O3 123.7(3) . . . . ? C2 C3 C5 C10 0.2(3) . . . . ? C4 C3 C5 C10 179.9(2) . . . . ? C2 C3 C5 C6 178.3(2) . . . . ? C4 C3 C5 C6 -2.0(4) . . . . ? C10 C5 C6 C7 -0.8(4) . . . . ? C3 C5 C6 C7 -178.9(3) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 N2 179.4(3) . . . . ? C8 C9 C10 C5 -1.1(4) . . . . ? C6 C5 C10 N2 -179.2(2) . . . . ? C3 C5 C10 N2 -0.9(3) . . . . ? C6 C5 C10 C9 1.4(4) . . . . ? C3 C5 C10 C9 179.6(2) . . . . ? N1 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 -2.4(4) . . . . ? C11 C12 C13 N3 177.1(2) . . . . ? C12 C13 C14 C15 3.1(5) . . . . ? N3 C13 C14 C15 -176.4(3) . . . . ? C13 C14 C15 N1 -1.2(5) . . . . ? C12 C11 N1 C15 2.2(4) . . . . ? C12 C11 N1 Zn1 -171.94(19) . . . . ? C14 C15 N1 C11 -1.4(5) . . . . ? C14 C15 N1 Zn1 172.6(3) . . . . ? O5 C1 N2 C10 -177.2(2) . . . . ? C2 C1 N2 C10 2.7(4) . . . . ? C9 C10 N2 C1 178.8(2) . . . . ? C5 C10 N2 C1 -0.6(4) . . . . ? C12 C13 N3 N3 179.6(3) . . . 2_556 ? C14 C13 N3 N3 -0.8(5) . . . 2_556 ? C11 N1 Zn1 O2 -42.40(18) . . . . ? C15 N1 Zn1 O2 143.8(2) . . . . ? C11 N1 Zn1 O2 137.60(18) . . . 2_557 ? C15 N1 Zn1 O2 -36.2(2) . . . 2_557 ? C11 N1 Zn1 O1 -133.28(18) . . . 2_557 ? C15 N1 Zn1 O1 52.9(2) . . . 2_557 ? C11 N1 Zn1 O1 46.72(18) . . . . ? C15 N1 Zn1 O1 -127.1(2) . . . . ? C11 N1 Zn1 N1 29(100) . . . 2_557 ? C15 N1 Zn1 N1 -144(100) . . . 2_557 ? 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 O8 H8A O1 0.85 2.27 2.999(3) 144.5 2_667 O7 H7B O4 0.85 1.87 2.719(3) 172.7 1_655 O6 H6A O4 0.85 2.08 2.900(3) 161.6 1_655 O8 H8B O7 0.85 2.00 2.833(3) 167.2 1_455 O2 H2B O6 0.85 1.86 2.709(3) 173.8 2_657 O1 H1B O7 0.86 1.88 2.719(3) 162.3 2_667 O2 H2A O8 0.85 2.01 2.767(3) 146.9 2_667 N2 H2C O5 0.86 1.99 2.849(3) 178.0 2_666 O6 H6B O3 0.85 1.99 2.823(3) 167.3 . O7 H7A O5 0.85 1.91 2.751(3) 171.2 . O1 H1A O3 0.85 1.82 2.667(3) 170.5 . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.376 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.060