# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email lidongsheng1@126.com _publ_contact_author_name 'Dong-Sheng Li' _publ_author_name 'Dong-Sheng Li' data_t _database_code_depnum_ccdc_archive 'CCDC 833936' #TrackingRef '- cif-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 N3 O6 Zn' _chemical_formula_weight 448.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4133(9) _cell_length_b 11.8185(11) _cell_length_c 14.8969(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.08 _cell_angle_gamma 90.00 _cell_volume 1833.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.384 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12102 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4514 _reflns_number_gt 3658 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The H atoms of lattice water O atoms were visible in the difference Fourier map and were included in the refinement with O DH distance restraint of 0.90 ?, and with Uiso(H) = 1.5Ueq(O). ; _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^)+(0.0471P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4514 _refine_ls_number_parameters 268 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.28272(3) -0.02665(3) 0.16024(2) 0.02771(11) Uani 1 1 d . . . N3 N 0.6576(2) 0.50340(19) -0.24022(15) 0.0279(5) Uani 1 1 d . . . N1 N 0.3369(2) 0.13280(19) 0.12281(15) 0.0290(5) Uani 1 1 d . . . N2 N 0.3819(2) 0.40948(19) -0.05034(15) 0.0288(5) Uani 1 1 d . . . H2A H 0.3165 0.4538 -0.0493 0.035 Uiso 1 1 calc R . . O3 O 0.55929(19) -0.27822(18) 0.37098(14) 0.0423(5) Uani 1 1 d . . . O1 O 0.43641(19) -0.11612(18) 0.16804(13) 0.0418(5) Uani 1 1 d . . . O4 O 0.6813(2) -0.44427(19) 0.55199(15) 0.0508(6) Uani 1 1 d . . . C12 C 0.3763(2) 0.3192(2) 0.00860(17) 0.0260(6) Uani 1 1 d . . . C19 C 0.4466(3) 0.5159(2) -0.17852(19) 0.0326(6) Uani 1 1 d . . . H19 H 0.3651 0.5477 -0.1815 0.039 Uiso 1 1 calc R . . C15 C 0.4767(2) 0.4390(2) -0.11043(18) 0.0258(6) Uani 1 1 d . . . C16 C 0.6031(3) 0.4011(2) -0.10750(19) 0.0330(7) Uani 1 1 d . . . H16 H 0.6298 0.3532 -0.0616 0.040 Uiso 1 1 calc R . . C2 C 0.6223(2) -0.1831(2) 0.23941(18) 0.0286(6) Uani 1 1 d . . . C1 C 0.5007(3) -0.1139(2) 0.24105(19) 0.0272(6) Uani 1 1 d . . . C13 C 0.2695(3) 0.3132(2) 0.06634(19) 0.0309(6) Uani 1 1 d . . . H13 H 0.2097 0.3716 0.0677 0.037 Uiso 1 1 calc R . . C11 C 0.4632(3) 0.2301(2) 0.01292(19) 0.0342(7) Uani 1 1 d . . . H11 H 0.5369 0.2310 -0.0223 0.041 Uiso 1 1 calc R . . O2 O 0.4697(2) -0.05782(19) 0.30678(14) 0.0438(6) Uani 1 1 d . . . C7 C 0.7086(3) -0.1684(3) 0.1697(2) 0.0372(7) Uani 1 1 d . . . H7 H 0.6905 -0.1153 0.1254 0.045 Uiso 1 1 calc R . . C3 C 0.6505(3) -0.2633(2) 0.3056(2) 0.0329(7) Uani 1 1 d . . . C14 C 0.2548(3) 0.2207(2) 0.12032(19) 0.0319(6) Uani 1 1 d . . . H14 H 0.1835 0.2184 0.1578 0.038 Uiso 1 1 calc R . . C10 C 0.4397(3) 0.1416(3) 0.06912(19) 0.0341(7) Uani 1 1 d . . . H10 H 0.4993 0.0830 0.0703 0.041 Uiso 1 1 calc R . . O5 O 0.6889(3) -0.2598(2) 0.53279(18) 0.0728(9) Uani 1 1 d . . . C5 C 0.8473(3) -0.3077(3) 0.2307(3) 0.0514(9) Uani 1 1 d . . . H5 H 0.9228 -0.3496 0.2282 0.062 Uiso 1 1 calc R . . C6 C 0.8209(3) -0.2306(3) 0.1642(2) 0.0453(8) Uani 1 1 d . . . H6 H 0.8772 -0.2203 0.1166 0.054 Uiso 1 1 calc R . . C4 C 0.7641(3) -0.3241(3) 0.3009(2) 0.0471(8) Uani 1 1 d . . . H4 H 0.7840 -0.3763 0.3455 0.057 Uiso 1 1 calc R . . O1W O 0.1562(2) 0.5425(2) 0.94910(18) 0.0514(6) Uani 1 1 d D . . C18 C 0.5373(3) 0.5439(2) -0.24048(19) 0.0333(7) Uani 1 1 d . . . H18 H 0.5144 0.5942 -0.2857 0.040 Uiso 1 1 calc R . . C17 C 0.6881(3) 0.4345(3) -0.17215(19) 0.0319(6) Uani 1 1 d . . . H17 H 0.7719 0.4077 -0.1686 0.038 Uiso 1 1 calc R . . C9 C 0.6561(3) -0.3537(3) 0.5112(2) 0.0369(7) Uani 1 1 d . . . C8 C 0.5716(3) -0.3729(3) 0.4294(2) 0.0451(8) Uani 1 1 d . . . H8A H 0.6064 -0.4358 0.3954 0.054 Uiso 1 1 calc R . . H8B H 0.4867 -0.3947 0.4497 0.054 Uiso 1 1 calc R . . H1WA H 0.091(2) 0.537(3) 0.911(2) 0.068 Uiso 1 1 d D . . H1WB H 0.156(3) 0.6116(15) 0.972(2) 0.068 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02787(18) 0.02878(19) 0.02647(19) -0.00102(13) -0.00211(13) 0.00338(14) N3 0.0282(12) 0.0286(13) 0.0270(13) 0.0015(9) 0.0005(10) 0.0014(10) N1 0.0265(12) 0.0320(13) 0.0285(13) -0.0006(10) 0.0004(10) 0.0008(10) N2 0.0255(12) 0.0291(13) 0.0319(13) 0.0036(10) 0.0021(10) 0.0040(10) O3 0.0386(12) 0.0445(14) 0.0439(13) 0.0187(10) -0.0064(10) -0.0032(10) O1 0.0400(12) 0.0500(14) 0.0354(12) -0.0064(10) -0.0118(10) 0.0191(10) O4 0.0638(15) 0.0409(14) 0.0474(14) 0.0168(11) -0.0282(12) -0.0129(11) C12 0.0275(14) 0.0253(14) 0.0251(14) -0.0031(11) -0.0009(11) -0.0025(11) C19 0.0293(14) 0.0343(16) 0.0342(17) 0.0030(13) 0.0000(12) 0.0093(12) C15 0.0270(14) 0.0240(14) 0.0263(14) -0.0038(11) -0.0027(11) -0.0005(11) C16 0.0299(15) 0.0365(17) 0.0325(16) 0.0101(13) -0.0057(12) -0.0002(13) C2 0.0258(14) 0.0288(15) 0.0313(15) -0.0026(12) -0.0054(11) -0.0009(11) C1 0.0262(14) 0.0241(14) 0.0313(15) 0.0062(12) 0.0000(12) -0.0026(11) C13 0.0262(14) 0.0299(15) 0.0365(16) -0.0034(12) 0.0042(12) 0.0054(12) C11 0.0278(14) 0.0357(17) 0.0391(17) 0.0029(13) 0.0106(12) 0.0032(13) O2 0.0424(13) 0.0492(14) 0.0396(13) -0.0097(10) -0.0057(10) 0.0144(11) C7 0.0343(16) 0.0421(18) 0.0353(17) -0.0045(14) -0.0052(13) -0.0058(14) C3 0.0278(14) 0.0311(16) 0.0397(17) 0.0022(13) -0.0082(13) -0.0038(12) C14 0.0285(15) 0.0329(16) 0.0344(16) -0.0016(12) 0.0082(12) 0.0004(12) C10 0.0267(15) 0.0347(17) 0.0407(18) 0.0026(13) 0.0020(12) 0.0055(12) O5 0.094(2) 0.0408(16) 0.084(2) 0.0060(13) -0.0522(17) -0.0173(14) C5 0.0318(17) 0.050(2) 0.072(3) -0.0180(19) -0.0116(17) 0.0117(16) C6 0.0301(16) 0.060(2) 0.045(2) -0.0195(17) -0.0015(14) -0.0031(15) C4 0.0390(18) 0.041(2) 0.061(2) 0.0039(16) -0.0130(17) 0.0070(15) O1W 0.0462(14) 0.0448(15) 0.0632(17) -0.0036(12) -0.0166(12) 0.0162(12) C18 0.0351(16) 0.0344(17) 0.0303(16) 0.0061(12) -0.0002(12) 0.0082(13) C17 0.0238(14) 0.0327(16) 0.0393(17) 0.0034(13) -0.0018(12) 0.0030(12) C9 0.0304(15) 0.0384(18) 0.0420(18) 0.0087(14) -0.0072(13) -0.0097(13) C8 0.0483(19) 0.042(2) 0.045(2) 0.0188(15) -0.0184(15) -0.0152(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9215(19) . ? Zn1 O4 1.957(2) 4 ? Zn1 N3 1.994(2) 4_566 ? Zn1 N1 2.045(2) . ? N3 C17 1.339(3) . ? N3 C18 1.341(3) . ? N3 Zn1 1.994(2) 4_665 ? N1 C10 1.341(3) . ? N1 C14 1.346(3) . ? N2 C15 1.378(3) . ? N2 C12 1.383(3) . ? N2 H2A 0.8600 . ? O3 C3 1.373(3) . ? O3 C8 1.423(3) . ? O1 C1 1.277(3) . ? O4 C9 1.258(3) . ? O4 Zn1 1.957(2) 4_656 ? C12 C11 1.390(4) . ? C12 C13 1.408(4) . ? C19 C18 1.362(4) . ? C19 C15 1.397(4) . ? C19 H19 0.9300 . ? C15 C16 1.391(4) . ? C16 C17 1.367(4) . ? C16 H16 0.9300 . ? C2 C7 1.385(4) . ? C2 C3 1.399(4) . ? C2 C1 1.507(4) . ? C1 O2 1.226(3) . ? C13 C14 1.365(4) . ? C13 H13 0.9300 . ? C11 C10 1.363(4) . ? C11 H11 0.9300 . ? C7 C6 1.383(4) . ? C7 H7 0.9300 . ? C3 C4 1.386(4) . ? C14 H14 0.9300 . ? C10 H10 0.9300 . ? O5 C9 1.205(4) . ? C5 C4 1.372(5) . ? C5 C6 1.374(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C4 H4 0.9300 . ? O1W H1WA 0.888(10) . ? O1W H1WB 0.886(10) . ? C18 H18 0.9300 . ? C17 H17 0.9300 . ? C9 C8 1.519(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 113.69(9) . 4 ? O1 Zn1 N3 125.15(9) . 4_566 ? O4 Zn1 N3 106.53(10) 4 4_566 ? O1 Zn1 N1 107.07(9) . . ? O4 Zn1 N1 94.93(10) 4 . ? N3 Zn1 N1 104.87(9) 4_566 . ? C17 N3 C18 116.1(2) . . ? C17 N3 Zn1 119.52(18) . 4_665 ? C18 N3 Zn1 124.05(19) . 4_665 ? C10 N1 C14 115.5(2) . . ? C10 N1 Zn1 117.04(19) . . ? C14 N1 Zn1 122.94(18) . . ? C15 N2 C12 129.7(2) . . ? C15 N2 H2A 115.2 . . ? C12 N2 H2A 115.2 . . ? C3 O3 C8 118.2(2) . . ? C1 O1 Zn1 118.42(18) . . ? C9 O4 Zn1 131.2(2) . 4_656 ? N2 C12 C11 125.8(2) . . ? N2 C12 C13 117.4(2) . . ? C11 C12 C13 116.6(3) . . ? C18 C19 C15 119.7(3) . . ? C18 C19 H19 120.2 . . ? C15 C19 H19 120.2 . . ? N2 C15 C16 125.2(2) . . ? N2 C15 C19 118.5(2) . . ? C16 C15 C19 116.3(2) . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C7 C2 C3 118.5(3) . . ? C7 C2 C1 119.3(3) . . ? C3 C2 C1 122.2(2) . . ? O2 C1 O1 123.6(3) . . ? O2 C1 C2 121.9(2) . . ? O1 C1 C2 114.5(2) . . ? C14 C13 C12 119.3(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C6 C7 C2 121.9(3) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? O3 C3 C4 124.1(3) . . ? O3 C3 C2 116.2(2) . . ? C4 C3 C2 119.6(3) . . ? N1 C14 C13 124.2(3) . . ? N1 C14 H14 117.9 . . ? C13 C14 H14 117.9 . . ? N1 C10 C11 124.8(3) . . ? N1 C10 H10 117.6 . . ? C11 C10 H10 117.6 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C7 118.5(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? H1WA O1W H1WB 108.3(15) . . ? N3 C18 C19 124.0(3) . . ? N3 C18 H18 118.0 . . ? C19 C18 H18 118.0 . . ? N3 C17 C16 123.8(3) . . ? N3 C17 H17 118.1 . . ? C16 C17 H17 118.1 . . ? O5 C9 O4 126.6(3) . . ? O5 C9 C8 121.0(3) . . ? O4 C9 C8 112.3(3) . . ? O3 C8 C9 115.1(2) . . ? O3 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? O3 C8 H8B 108.5 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 N1 C10 32.2(2) . . . . ? O4 Zn1 N1 C10 -84.4(2) 4 . . . ? N3 Zn1 N1 C10 167.02(19) 4_566 . . . ? O1 Zn1 N1 C14 -172.6(2) . . . . ? O4 Zn1 N1 C14 70.7(2) 4 . . . ? N3 Zn1 N1 C14 -37.8(2) 4_566 . . . ? O4 Zn1 O1 C1 -171.4(2) 4 . . . ? N3 Zn1 O1 C1 -37.9(2) 4_566 . . . ? N1 Zn1 O1 C1 85.1(2) . . . . ? C15 N2 C12 C11 -7.1(5) . . . . ? C15 N2 C12 C13 176.6(3) . . . . ? C12 N2 C15 C16 -18.7(5) . . . . ? C12 N2 C15 C19 163.5(3) . . . . ? C18 C19 C15 N2 -178.0(3) . . . . ? C18 C19 C15 C16 4.0(4) . . . . ? N2 C15 C16 C17 178.6(3) . . . . ? C19 C15 C16 C17 -3.6(4) . . . . ? Zn1 O1 C1 O2 0.2(4) . . . . ? Zn1 O1 C1 C2 -177.74(18) . . . . ? C7 C2 C1 O2 -126.9(3) . . . . ? C3 C2 C1 O2 54.0(4) . . . . ? C7 C2 C1 O1 51.1(4) . . . . ? C3 C2 C1 O1 -128.1(3) . . . . ? N2 C12 C13 C14 174.6(3) . . . . ? C11 C12 C13 C14 -2.0(4) . . . . ? N2 C12 C11 C10 -174.2(3) . . . . ? C13 C12 C11 C10 2.1(4) . . . . ? C3 C2 C7 C6 -0.1(4) . . . . ? C1 C2 C7 C6 -179.2(3) . . . . ? C8 O3 C3 C4 -10.2(4) . . . . ? C8 O3 C3 C2 168.2(3) . . . . ? C7 C2 C3 O3 -177.2(2) . . . . ? C1 C2 C3 O3 1.9(4) . . . . ? C7 C2 C3 C4 1.2(4) . . . . ? C1 C2 C3 C4 -179.6(3) . . . . ? C10 N1 C14 C13 1.5(4) . . . . ? Zn1 N1 C14 C13 -154.0(2) . . . . ? C12 C13 C14 N1 0.2(4) . . . . ? C14 N1 C10 C11 -1.5(4) . . . . ? Zn1 N1 C10 C11 155.5(2) . . . . ? C12 C11 C10 N1 -0.4(5) . . . . ? C4 C5 C6 C7 0.6(5) . . . . ? C2 C7 C6 C5 -0.8(5) . . . . ? C6 C5 C4 C3 0.6(5) . . . . ? O3 C3 C4 C5 176.8(3) . . . . ? C2 C3 C4 C5 -1.5(5) . . . . ? C17 N3 C18 C19 -2.3(4) . . . . ? Zn1 N3 C18 C19 170.9(2) 4_665 . . . ? C15 C19 C18 N3 -1.1(5) . . . . ? C18 N3 C17 C16 2.8(4) . . . . ? Zn1 N3 C17 C16 -170.8(2) 4_665 . . . ? C15 C16 C17 N3 0.2(5) . . . . ? Zn1 O4 C9 O5 -1.9(6) 4_656 . . . ? Zn1 O4 C9 C8 -179.6(2) 4_656 . . . ? C3 O3 C8 C9 86.3(3) . . . . ? O5 C9 C8 O3 13.4(5) . . . . ? O4 C9 C8 O3 -168.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.497 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.074 # Attachment '- cif-2.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 833937' #TrackingRef '- cif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H50 N4 O15 Zn2' _chemical_formula_weight 1005.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 22.479(7) _cell_length_b 13.058(4) _cell_length_c 17.853(10) _cell_angle_alpha 90.00 _cell_angle_beta 119.695(4) _cell_angle_gamma 90.00 _cell_volume 4552(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 1.127 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.752 _exptl_absorpt_correction_T_max 0.789 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11700 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4024 _reflns_number_gt 3186 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0861P)^2^+2.7673P] 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 4024 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.251802(17) 0.37472(3) 0.21113(2) 0.06072(17) Uani 1 1 d . . . N1 N 0.21269(11) 0.32764(18) 0.28661(16) 0.0559(6) Uani 1 1 d . . . N2 N -0.15845(12) -0.04652(18) 0.28890(16) 0.0562(6) Uani 1 1 d . . . O1 O 0.29321(14) 0.24882(19) 0.20316(18) 0.0850(7) Uani 1 1 d . . . O2 O 0.3352(2) 0.1170(2) 0.1713(3) 0.1308(13) Uani 1 1 d . . . O3 O 0.17525(13) 0.32669(19) 0.07068(17) 0.0785(6) Uani 1 1 d . . . O4 O 0.19959(12) 0.49794(17) 0.15424(16) 0.0756(6) Uani 1 1 d . . . O5 O 0.11271(15) 0.5784(2) 0.0475(2) 0.1029(9) Uani 1 1 d . . . C1 C 0.2876(2) 0.1795(3) 0.1495(3) 0.0889(13) Uani 1 1 d . . . C2 C 0.2258(2) 0.1717(3) 0.0616(3) 0.0813(11) Uani 1 1 d . . . C3 C 0.1731(2) 0.2404(3) 0.0241(3) 0.0803(10) Uani 1 1 d . . . C4 C 0.1191(3) 0.2254(4) -0.0600(3) 0.0999(14) Uani 1 1 d . . . H4 H 0.0833 0.2721 -0.0848 0.120 Uiso 1 1 calc R . . C5 C 0.1199(3) 0.1406(5) -0.1054(4) 0.1148(19) Uani 1 1 d . . . H5 H 0.0845 0.1310 -0.1616 0.138 Uiso 1 1 calc R . . C6 C 0.1708(4) 0.0715(4) -0.0699(5) 0.120(2) Uani 1 1 d . . . H6 H 0.1704 0.0149 -0.1017 0.144 Uiso 1 1 calc R . . C7 C 0.2232(3) 0.0841(3) 0.0127(4) 0.1070(16) Uani 1 1 d . . . H7 H 0.2575 0.0348 0.0372 0.128 Uiso 1 1 calc R . . C8 C 0.1285(2) 0.4072(3) 0.0241(3) 0.0814(10) Uani 1 1 d . . . H8A H 0.0823 0.3867 0.0085 0.098 Uiso 1 1 calc R . . H8B H 0.1297 0.4215 -0.0284 0.098 Uiso 1 1 calc R . . C9 C 0.14798(18) 0.5014(3) 0.0794(2) 0.0742(9) Uani 1 1 d . . . C10 C 0.23998(15) 0.2480(2) 0.3391(2) 0.0587(7) Uani 1 1 d . . . H10 H 0.2784 0.2167 0.3426 0.070 Uiso 1 1 calc R . . C11 C 0.21392(15) 0.2102(2) 0.3883(2) 0.0602(7) Uani 1 1 d . . . H11 H 0.2350 0.1545 0.4243 0.072 Uiso 1 1 calc R . . C12 C 0.15663(14) 0.2536(2) 0.38513(19) 0.0561(7) Uani 1 1 d . . . C13 C 0.12913(17) 0.3376(3) 0.3314(3) 0.0727(9) Uani 1 1 d . . . H13 H 0.0910 0.3705 0.3275 0.087 Uiso 1 1 calc R . . C14 C 0.15755(17) 0.3726(2) 0.2837(3) 0.0694(9) Uani 1 1 d . . . H14 H 0.1382 0.4293 0.2483 0.083 Uiso 1 1 calc R . . C15 C 0.12577(15) 0.2128(3) 0.4363(2) 0.0626(7) Uani 1 1 d . . . H15A H 0.1212 0.2683 0.4693 0.075 Uiso 1 1 calc R . . H15B H 0.1566 0.1623 0.4769 0.075 Uiso 1 1 calc R . . C16 C 0.05575(15) 0.1635(3) 0.38084(19) 0.0599(7) Uani 1 1 d . . . H16A H 0.0241 0.2139 0.3411 0.072 Uiso 1 1 calc R . . H16B H 0.0596 0.1082 0.3472 0.072 Uiso 1 1 calc R . . C17 C 0.02819(18) 0.1219(3) 0.4373(2) 0.0730(9) Uani 1 1 d . . . H17A H 0.0621 0.0767 0.4806 0.088 Uiso 1 1 calc R . . H17B H 0.0209 0.1784 0.4671 0.088 Uiso 1 1 calc R . . C18 C -0.03780(15) 0.0642(2) 0.38653(19) 0.0598(7) Uani 1 1 d . . . C19 C -0.10078(17) 0.1092(2) 0.3551(2) 0.0670(8) Uani 1 1 d . . . H19 H -0.1039 0.1780 0.3661 0.080 Uiso 1 1 calc R . . C20 C -0.15925(16) 0.0531(2) 0.3074(2) 0.0657(8) Uani 1 1 d . . . H20 H -0.2014 0.0854 0.2869 0.079 Uiso 1 1 calc R . . C21 C -0.09759(17) -0.0912(3) 0.3210(2) 0.0685(8) Uani 1 1 d . . . H21 H -0.0956 -0.1605 0.3105 0.082 Uiso 1 1 calc R . . C22 C -0.03722(16) -0.0384(3) 0.3694(2) 0.0735(9) Uani 1 1 d . . . H22 H 0.0044 -0.0726 0.3907 0.088 Uiso 1 1 calc R . . O6 O 0.4406(2) 0.1394(3) 0.3403(4) 0.174(2) Uani 1 1 d . . . O7 O 0.9907(2) 0.5921(5) 0.8895(3) 0.213(3) Uani 1 1 d . . . O8 O 0.0000 0.2512(16) 0.7500 0.486(14) 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 Zn1 0.0592(3) 0.0514(2) 0.0789(3) 0.00008(15) 0.0398(2) -0.00657(15) N1 0.0499(13) 0.0470(12) 0.0757(15) -0.0001(12) 0.0347(12) -0.0058(10) N2 0.0533(13) 0.0545(13) 0.0699(15) 0.0030(11) 0.0376(12) -0.0017(11) O1 0.0922(17) 0.0645(14) 0.1111(19) -0.0060(14) 0.0601(16) 0.0061(13) O2 0.164(3) 0.081(2) 0.176(4) 0.004(2) 0.105(3) 0.034(2) O3 0.0864(16) 0.0695(14) 0.0891(16) -0.0169(13) 0.0507(14) -0.0126(13) O4 0.0735(14) 0.0551(12) 0.0796(15) 0.0014(11) 0.0237(13) -0.0063(11) O5 0.0907(18) 0.0737(17) 0.0992(19) 0.0177(15) 0.0128(16) 0.0006(15) C1 0.123(3) 0.0486(18) 0.144(4) 0.008(2) 0.103(3) 0.001(2) C2 0.106(3) 0.064(2) 0.112(3) -0.016(2) 0.083(3) -0.028(2) C3 0.099(3) 0.072(2) 0.105(3) -0.021(2) 0.077(2) -0.032(2) C4 0.114(3) 0.106(3) 0.106(3) -0.039(3) 0.075(3) -0.052(3) C5 0.141(5) 0.118(4) 0.122(4) -0.048(3) 0.093(4) -0.066(4) C6 0.174(6) 0.092(3) 0.155(5) -0.050(4) 0.127(5) -0.055(4) C7 0.153(4) 0.075(2) 0.153(5) -0.026(3) 0.122(4) -0.037(3) C8 0.074(2) 0.082(2) 0.084(2) -0.0049(19) 0.036(2) -0.0144(19) C9 0.065(2) 0.066(2) 0.084(2) 0.0081(18) 0.0307(19) -0.0149(17) C10 0.0481(14) 0.0574(16) 0.0726(18) 0.0026(14) 0.0314(14) 0.0028(13) C11 0.0529(15) 0.0564(16) 0.0682(18) 0.0059(14) 0.0276(14) 0.0018(13) C12 0.0481(15) 0.0546(16) 0.0648(17) -0.0068(13) 0.0273(13) -0.0125(12) C13 0.0603(18) 0.0641(18) 0.108(3) 0.0118(19) 0.0520(19) 0.0095(16) C14 0.0640(19) 0.0584(18) 0.097(2) 0.0176(16) 0.0482(18) 0.0075(14) C15 0.0541(16) 0.0706(19) 0.0646(17) -0.0048(15) 0.0306(14) -0.0131(14) C16 0.0529(15) 0.0680(18) 0.0588(16) 0.0001(14) 0.0277(14) -0.0134(14) C17 0.0624(19) 0.096(3) 0.0642(19) -0.0005(17) 0.0339(16) -0.0219(17) C18 0.0572(17) 0.074(2) 0.0582(16) 0.0046(14) 0.0362(14) -0.0106(15) C19 0.0635(19) 0.0589(17) 0.077(2) -0.0058(15) 0.0335(17) -0.0034(15) C20 0.0544(17) 0.0604(18) 0.085(2) -0.0027(16) 0.0369(17) 0.0020(14) C21 0.0615(19) 0.0578(17) 0.091(2) 0.0031(16) 0.0414(18) 0.0033(15) C22 0.0493(17) 0.079(2) 0.092(2) 0.0085(18) 0.0351(17) 0.0075(16) O6 0.128(3) 0.139(4) 0.269(6) 0.037(4) 0.109(4) 0.016(3) O7 0.110(3) 0.254(6) 0.166(4) 0.082(4) -0.014(3) -0.062(4) O8 0.52(3) 0.39(2) 0.72(4) 0.000 0.43(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 Zn1 O1 1.929(2) . ? Zn1 O4 1.954(2) . ? Zn1 N1 2.035(2) . ? Zn1 N2 2.069(2) 3 ? Zn1 O3 2.317(3) . ? N1 C10 1.330(4) . ? N1 C14 1.349(4) . ? N2 C21 1.328(4) . ? N2 C20 1.344(4) . ? N2 Zn1 2.069(2) 3_445 ? O1 C1 1.277(5) . ? O2 C1 1.246(5) . ? O3 C3 1.387(4) . ? O3 C8 1.427(5) . ? O4 C9 1.264(4) . ? O5 C9 1.232(4) . ? C1 C2 1.499(6) . ? C2 C3 1.367(6) . ? C2 C7 1.422(6) . ? C3 C4 1.400(6) . ? C4 C5 1.377(7) . ? C4 H4 0.9300 . ? C5 C6 1.344(8) . ? C5 H5 0.9300 . ? C6 C7 1.366(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.500(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C11 1.366(4) . ? C10 H10 0.9300 . ? C11 C12 1.383(4) . ? C11 H11 0.9300 . ? C12 C13 1.385(5) . ? C12 C15 1.493(4) . ? C13 C14 1.371(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.526(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.522(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.502(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.370(5) . ? C18 C22 1.376(5) . ? C19 C20 1.371(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.379(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 148.33(12) . . ? O1 Zn1 N1 100.02(11) . . ? O4 Zn1 N1 104.34(10) . . ? O1 Zn1 N2 97.32(11) . 3 ? O4 Zn1 N2 94.27(9) . 3 ? N1 Zn1 N2 107.66(10) . 3 ? O1 Zn1 O3 79.41(11) . . ? O4 Zn1 O3 74.18(10) . . ? N1 Zn1 O3 107.58(10) . . ? N2 Zn1 O3 144.63(9) 3 . ? C10 N1 C14 117.5(3) . . ? C10 N1 Zn1 120.24(19) . . ? C14 N1 Zn1 122.2(2) . . ? C21 N2 C20 117.1(3) . . ? C21 N2 Zn1 121.7(2) . 3_445 ? C20 N2 Zn1 121.2(2) . 3_445 ? C1 O1 Zn1 141.9(3) . . ? C3 O3 C8 116.9(3) . . ? C3 O3 Zn1 130.9(3) . . ? C8 O3 Zn1 111.7(2) . . ? C9 O4 Zn1 125.4(2) . . ? O2 C1 O1 118.7(5) . . ? O2 C1 C2 119.3(4) . . ? O1 C1 C2 122.0(4) . . ? C3 C2 C7 117.7(5) . . ? C3 C2 C1 126.6(3) . . ? C7 C2 C1 115.7(4) . . ? C2 C3 O3 118.4(4) . . ? C2 C3 C4 120.9(4) . . ? O3 C3 C4 120.7(4) . . ? C5 C4 C3 119.1(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 121.2(6) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.4(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 120.6(6) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? O3 C8 C9 109.3(3) . . ? O3 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? O3 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O5 C9 O4 124.1(4) . . ? O5 C9 C8 117.0(3) . . ? O4 C9 C8 118.8(3) . . ? N1 C10 C11 122.7(3) . . ? N1 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C10 C11 C12 120.9(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 116.1(3) . . ? C11 C12 C15 122.3(3) . . ? C13 C12 C15 121.6(3) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? N1 C14 C13 122.2(3) . . ? N1 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C12 C15 C16 113.3(2) . . ? C12 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C12 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 110.4(2) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C18 C17 C16 112.5(3) . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C19 C18 C22 116.6(3) . . ? C19 C18 C17 122.9(3) . . ? C22 C18 C17 120.5(3) . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? N2 C20 C19 123.0(3) . . ? N2 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? N2 C21 C22 122.3(3) . . ? N2 C21 H21 118.8 . . ? C22 C21 H21 118.8 . . ? C18 C22 C21 120.7(3) . . ? C18 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 N1 C10 24.6(2) . . . . ? O4 Zn1 N1 C10 -175.8(2) . . . . ? N2 Zn1 N1 C10 -76.4(2) 3 . . . ? O3 Zn1 N1 C10 106.6(2) . . . . ? O1 Zn1 N1 C14 -153.1(3) . . . . ? O4 Zn1 N1 C14 6.5(3) . . . . ? N2 Zn1 N1 C14 105.8(3) 3 . . . ? O3 Zn1 N1 C14 -71.2(3) . . . . ? O4 Zn1 O1 C1 -27.7(5) . . . . ? N1 Zn1 O1 C1 112.3(4) . . . . ? N2 Zn1 O1 C1 -138.3(4) 3 . . . ? O3 Zn1 O1 C1 6.1(4) . . . . ? O1 Zn1 O3 C3 2.8(3) . . . . ? O4 Zn1 O3 C3 165.2(3) . . . . ? N1 Zn1 O3 C3 -94.5(3) . . . . ? N2 Zn1 O3 C3 90.6(3) 3 . . . ? O1 Zn1 O3 C8 -168.8(2) . . . . ? O4 Zn1 O3 C8 -6.4(2) . . . . ? N1 Zn1 O3 C8 94.0(2) . . . . ? N2 Zn1 O3 C8 -81.0(3) 3 . . . ? O1 Zn1 O4 C9 42.2(4) . . . . ? N1 Zn1 O4 C9 -97.0(3) . . . . ? N2 Zn1 O4 C9 153.5(3) 3 . . . ? O3 Zn1 O4 C9 7.6(3) . . . . ? Zn1 O1 C1 O2 168.0(3) . . . . ? Zn1 O1 C1 C2 -11.7(6) . . . . ? O2 C1 C2 C3 -171.8(4) . . . . ? O1 C1 C2 C3 7.9(5) . . . . ? O2 C1 C2 C7 7.1(5) . . . . ? O1 C1 C2 C7 -173.2(3) . . . . ? C7 C2 C3 O3 -179.4(3) . . . . ? C1 C2 C3 O3 -0.5(5) . . . . ? C7 C2 C3 C4 -0.9(5) . . . . ? C1 C2 C3 C4 178.0(3) . . . . ? C8 O3 C3 C2 166.6(3) . . . . ? Zn1 O3 C3 C2 -4.7(4) . . . . ? C8 O3 C3 C4 -12.0(4) . . . . ? Zn1 O3 C3 C4 176.8(2) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? O3 C3 C4 C5 177.8(3) . . . . ? C3 C4 C5 C6 1.1(7) . . . . ? C4 C5 C6 C7 0.1(7) . . . . ? C5 C6 C7 C2 -1.8(7) . . . . ? C3 C2 C7 C6 2.1(5) . . . . ? C1 C2 C7 C6 -176.9(4) . . . . ? C3 O3 C8 C9 -167.9(3) . . . . ? Zn1 O3 C8 C9 5.0(3) . . . . ? Zn1 O4 C9 O5 174.1(3) . . . . ? Zn1 O4 C9 C8 -7.3(5) . . . . ? O3 C8 C9 O5 179.0(3) . . . . ? O3 C8 C9 O4 0.3(5) . . . . ? C14 N1 C10 C11 0.9(4) . . . . ? Zn1 N1 C10 C11 -176.9(2) . . . . ? N1 C10 C11 C12 0.3(5) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C10 C11 C12 C15 178.5(3) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? C15 C12 C13 C14 -178.8(3) . . . . ? C10 N1 C14 C13 -1.2(5) . . . . ? Zn1 N1 C14 C13 176.6(3) . . . . ? C12 C13 C14 N1 0.2(6) . . . . ? C11 C12 C15 C16 -111.3(3) . . . . ? C13 C12 C15 C16 68.5(4) . . . . ? C12 C15 C16 C17 178.9(3) . . . . ? C15 C16 C17 C18 -174.9(3) . . . . ? C16 C17 C18 C19 -93.3(4) . . . . ? C16 C17 C18 C22 86.7(4) . . . . ? C22 C18 C19 C20 -1.6(5) . . . . ? C17 C18 C19 C20 178.5(3) . . . . ? C21 N2 C20 C19 1.7(5) . . . . ? Zn1 N2 C20 C19 -176.7(3) 3_445 . . . ? C18 C19 C20 N2 -0.1(5) . . . . ? C20 N2 C21 C22 -1.7(5) . . . . ? Zn1 N2 C21 C22 176.7(3) 3_445 . . . ? C19 C18 C22 C21 1.6(5) . . . . ? C17 C18 C22 C21 -178.4(3) . . . . ? N2 C21 C22 C18 0.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.875 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.064 # Attachment '- cif-3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 833938' #TrackingRef '- cif-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 N4 O8 Zn' _chemical_formula_weight 503.81 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 8.9846(2) _cell_length_b 9.2383(2) _cell_length_c 13.4394(3) _cell_angle_alpha 82.9500(10) _cell_angle_beta 83.4740(10) _cell_angle_gamma 84.5990(10) _cell_volume 1096.25(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_T_max 0.791 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16286 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 29.47 _reflns_number_total 6016 _reflns_number_gt 5183 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.2407P] 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 6016 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.14279(2) 0.74005(2) 0.247249(15) 0.03640(8) Uani 1 1 d . . . O1 O 0.21983(15) 0.53645(14) 0.22533(11) 0.0435(3) Uani 1 1 d . . . O3 O 0.32350(16) 0.26526(14) 0.17612(11) 0.0453(3) Uani 1 1 d . . . O5 O 0.30486(17) -0.15204(15) 0.27604(13) 0.0540(4) Uani 1 1 d . . . O4 O 0.14449(17) 0.04453(17) 0.27339(16) 0.0629(4) Uani 1 1 d . . . O2 O 0.3573(2) 0.64495(16) 0.09613(14) 0.0636(4) Uani 1 1 d . . . N1 N 0.01026(17) 0.80916(17) 0.13843(12) 0.0415(3) Uani 1 1 d . . . N2 N -0.17785(18) 0.92446(18) 0.06407(14) 0.0440(3) Uani 1 1 d . . . N3 N -0.00232(18) 0.70719(18) 0.37284(12) 0.0427(3) Uani 1 1 d . . . N4 N -0.17900(19) 0.6092(2) 0.47905(13) 0.0488(4) Uani 1 1 d . . . C4 C 0.4032(2) 0.06870(19) 0.29258(14) 0.0382(3) Uani 1 1 d . . . C3 C 0.4235(2) 0.20950(18) 0.24283(14) 0.0393(4) Uani 1 1 d . . . C9 C 0.2723(2) -0.01506(19) 0.27880(14) 0.0402(4) Uani 1 1 d . . . C1 C 0.3119(2) 0.53603(19) 0.14590(15) 0.0409(4) Uani 1 1 d . . . C5 C 0.5078(3) 0.0044(3) 0.35566(19) 0.0549(5) Uani 1 1 d . . . H5A H 0.4960 -0.0894 0.3879 0.066 Uiso 1 1 calc R . . C6 C 0.6297(3) 0.0759(3) 0.3720(2) 0.0682(7) Uani 1 1 d . . . H6A H 0.6985 0.0314 0.4154 0.082 Uiso 1 1 calc R . . C14 C -0.4325(2) 0.9487(2) 0.01170(19) 0.0500(5) Uani 1 1 d . . . H14B H -0.3952 0.9128 -0.0512 0.075 Uiso 1 1 d R . . H14A H -0.4603 0.8683 0.0605 0.075 Uiso 1 1 d R . . C16 C -0.0320(3) 0.7875(3) 0.4530(2) 0.0604(6) Uani 1 1 d . . . H16A H 0.0155 0.8698 0.4611 0.072 Uiso 1 1 calc R . . C12 C -0.1090(2) 0.9030(2) 0.14764(16) 0.0451(4) Uani 1 1 d . . . H9A H -0.1408 0.9484 0.2053 0.054 Uiso 1 1 calc R . . C17 C -0.1404(3) 0.7287(3) 0.5181(2) 0.0667(7) Uani 1 1 d . . . H17A H -0.1816 0.7628 0.5784 0.080 Uiso 1 1 calc R . . C15 C -0.0922(2) 0.5996(2) 0.39226(15) 0.0480(4) Uani 1 1 d . . . H15A H -0.0947 0.5266 0.3507 0.058 Uiso 1 1 calc R . . C11 C -0.0992(2) 0.8406(2) -0.00356(16) 0.0483(4) Uani 1 1 d . . . H11A H -0.1210 0.8336 -0.0687 0.058 Uiso 1 1 calc R . . C2 C 0.3600(3) 0.3898(2) 0.10699(16) 0.0510(5) Uani 1 1 d . . . H2A H 0.3131 0.3861 0.0459 0.061 Uiso 1 1 calc R . . H2B H 0.4680 0.3837 0.0892 0.061 Uiso 1 1 calc R . . C7 C 0.6477(3) 0.2142(3) 0.3230(2) 0.0673(7) Uani 1 1 d . . . H7A H 0.7300 0.2628 0.3329 0.081 Uiso 1 1 calc R . . C19 C -0.4423(2) 0.5543(3) 0.47911(18) 0.0551(5) Uani 1 1 d . . . H19B H -0.4780 0.6515 0.4936 0.083 Uiso 1 1 d R . . H19A H -0.4295 0.5514 0.4075 0.083 Uiso 1 1 d R . . C10 C 0.0172(2) 0.7691(2) 0.04274(16) 0.0472(4) Uani 1 1 d . . . H10A H 0.0900 0.7036 0.0144 0.057 Uiso 1 1 calc R . . C13 C -0.3139(2) 1.0226(2) 0.0478(2) 0.0574(6) Uani 1 1 d . . . H13A H -0.2874 1.1048 -0.0011 0.069 Uiso 1 1 calc R . . H13B H -0.3526 1.0607 0.1106 0.069 Uiso 1 1 calc R . . C18 C -0.2936(2) 0.5112(3) 0.52183(19) 0.0586(6) Uani 1 1 d . . . H18A H -0.3080 0.5123 0.5944 0.070 Uiso 1 1 calc R . . H18B H -0.2593 0.4122 0.5082 0.070 Uiso 1 1 calc R . . C8 C 0.5454(2) 0.2815(2) 0.25936(19) 0.0527(5) Uani 1 1 d . . . H8A H 0.5582 0.3754 0.2275 0.063 Uiso 1 1 calc R . . O2W O -0.00176(19) 0.3288(2) 0.24597(17) 0.0705(5) Uani 1 1 d . . . O1W O -0.1928(5) 0.4849(4) 0.1144(3) 0.1485(13) Uani 1 1 d . . . O3W O 0.6167(4) -0.3133(5) 0.2323(3) 0.1548(14) 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 Zn1 0.03591(12) 0.03041(11) 0.04262(13) -0.00237(8) -0.00466(8) -0.00291(7) O1 0.0513(7) 0.0310(6) 0.0475(7) -0.0076(5) 0.0016(6) -0.0033(5) O3 0.0541(8) 0.0293(6) 0.0508(8) -0.0009(5) -0.0013(6) -0.0039(5) O5 0.0523(8) 0.0310(6) 0.0816(11) -0.0086(7) -0.0130(7) -0.0084(6) O4 0.0443(8) 0.0414(8) 0.1035(14) -0.0041(8) -0.0098(8) -0.0090(6) O2 0.0721(10) 0.0346(7) 0.0757(11) 0.0074(7) 0.0138(8) -0.0040(7) N1 0.0379(7) 0.0423(8) 0.0436(8) -0.0034(6) -0.0057(6) 0.0006(6) N2 0.0370(7) 0.0416(8) 0.0546(10) -0.0071(7) -0.0117(7) 0.0004(6) N3 0.0413(8) 0.0445(8) 0.0421(8) -0.0082(7) -0.0015(6) -0.0021(6) N4 0.0417(8) 0.0592(10) 0.0423(9) -0.0010(7) 0.0010(6) -0.0002(7) C4 0.0415(8) 0.0308(8) 0.0425(9) -0.0067(7) 0.0006(7) -0.0072(6) C3 0.0418(9) 0.0291(8) 0.0467(9) -0.0090(7) 0.0035(7) -0.0048(6) C9 0.0459(9) 0.0313(8) 0.0437(9) -0.0021(7) -0.0027(7) -0.0097(7) C1 0.0433(9) 0.0299(8) 0.0481(10) -0.0024(7) -0.0025(7) -0.0006(6) C5 0.0615(13) 0.0463(11) 0.0580(13) 0.0010(9) -0.0142(10) -0.0082(9) C6 0.0597(13) 0.0725(16) 0.0774(17) -0.0108(13) -0.0259(12) -0.0057(12) C14 0.0409(9) 0.0418(10) 0.0695(13) -0.0094(9) -0.0180(9) 0.0043(8) C16 0.0658(14) 0.0556(13) 0.0620(14) -0.0241(11) 0.0047(11) -0.0066(10) C12 0.0412(9) 0.0496(10) 0.0454(10) -0.0116(8) -0.0069(7) 0.0021(8) C17 0.0710(15) 0.0744(16) 0.0534(13) -0.0229(12) 0.0139(11) -0.0026(12) C15 0.0456(10) 0.0567(12) 0.0421(10) -0.0100(8) 0.0017(8) -0.0087(8) C11 0.0428(9) 0.0565(12) 0.0471(10) -0.0095(9) -0.0082(8) -0.0027(8) C2 0.0716(13) 0.0318(9) 0.0451(10) -0.0024(7) 0.0089(9) -0.0014(8) C7 0.0518(12) 0.0620(14) 0.095(2) -0.0223(13) -0.0113(12) -0.0183(10) C19 0.0423(10) 0.0627(13) 0.0528(12) 0.0153(10) 0.0010(8) -0.0009(9) C10 0.0401(9) 0.0518(11) 0.0496(11) -0.0115(9) -0.0040(8) 0.0034(8) C13 0.0453(10) 0.0432(10) 0.0881(17) -0.0152(11) -0.0256(11) 0.0069(8) C18 0.0457(11) 0.0699(14) 0.0526(12) 0.0168(10) 0.0014(9) -0.0036(10) C8 0.0499(11) 0.0374(9) 0.0723(14) -0.0121(9) 0.0033(10) -0.0148(8) O2W 0.0498(9) 0.0605(10) 0.1014(15) -0.0172(10) -0.0005(9) -0.0031(7) O1W 0.173(3) 0.131(3) 0.145(3) 0.006(2) -0.047(3) -0.022(3) O3W 0.132(3) 0.191(4) 0.133(3) 0.029(3) -0.019(2) -0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O5 1.9390(14) 1_565 ? Zn1 O1 1.9870(13) . ? Zn1 N1 1.9970(15) . ? Zn1 N3 2.0223(16) . ? O1 C1 1.274(2) . ? O3 C3 1.363(2) . ? O3 C2 1.426(2) . ? O5 C9 1.276(2) . ? O5 Zn1 1.9390(14) 1_545 ? O4 C9 1.232(2) . ? O2 C1 1.215(2) . ? N1 C12 1.317(2) . ? N1 C10 1.374(3) . ? N2 C12 1.328(3) . ? N2 C11 1.360(3) . ? N2 C13 1.472(2) . ? N3 C15 1.322(3) . ? N3 C16 1.370(3) . ? N4 C15 1.335(3) . ? N4 C17 1.368(3) . ? N4 C18 1.457(3) . ? C4 C5 1.381(3) . ? C4 C3 1.406(2) . ? C4 C9 1.507(2) . ? C3 C8 1.386(3) . ? C1 C2 1.516(3) . ? C5 C6 1.382(3) . ? C5 H5A 0.9300 . ? C6 C7 1.380(4) . ? C6 H6A 0.9300 . ? C14 C13 1.474(3) . ? C14 C14 1.504(4) 2_475 ? C14 H14B 0.9602 . ? C14 H14A 0.9600 . ? C16 C17 1.341(4) . ? C16 H16A 0.9300 . ? C12 H9A 0.9300 . ? C17 H17A 0.9300 . ? C15 H15A 0.9300 . ? C11 C10 1.354(3) . ? C11 H11A 0.9300 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C7 C8 1.380(4) . ? C7 H7A 0.9300 . ? C19 C18 1.513(3) . ? C19 C19 1.524(4) 2_466 ? C19 H19B 0.9600 . ? C19 H19A 0.9600 . ? C10 H10A 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C8 H8A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Zn1 O1 110.00(6) 1_565 . ? O5 Zn1 N1 123.38(7) 1_565 . ? O1 Zn1 N1 106.13(6) . . ? O5 Zn1 N3 109.33(7) 1_565 . ? O1 Zn1 N3 101.77(6) . . ? N1 Zn1 N3 104.03(7) . . ? C1 O1 Zn1 110.40(11) . . ? C3 O3 C2 118.43(16) . . ? C9 O5 Zn1 115.21(13) . 1_545 ? C12 N1 C10 105.67(16) . . ? C12 N1 Zn1 124.81(14) . . ? C10 N1 Zn1 129.49(13) . . ? C12 N2 C11 107.61(16) . . ? C12 N2 C13 125.91(18) . . ? C11 N2 C13 126.47(18) . . ? C15 N3 C16 105.58(18) . . ? C15 N3 Zn1 124.94(14) . . ? C16 N3 Zn1 129.47(16) . . ? C15 N4 C17 106.68(19) . . ? C15 N4 C18 125.9(2) . . ? C17 N4 C18 127.4(2) . . ? C5 C4 C3 118.70(18) . . ? C5 C4 C9 118.89(17) . . ? C3 C4 C9 122.41(17) . . ? O3 C3 C8 123.28(17) . . ? O3 C3 C4 116.95(16) . . ? C8 C3 C4 119.69(19) . . ? O4 C9 O5 123.48(17) . . ? O4 C9 C4 122.18(16) . . ? O5 C9 C4 114.32(16) . . ? O2 C1 O1 124.72(17) . . ? O2 C1 C2 117.66(18) . . ? O1 C1 C2 117.48(16) . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? C7 C6 C5 118.9(2) . . ? C7 C6 H6A 120.6 . . ? C5 C6 H6A 120.6 . . ? C13 C14 C14 112.7(2) . 2_475 ? C13 C14 H14B 109.2 . . ? C14 C14 H14B 104.8 2_475 . ? C13 C14 H14A 109.3 . . ? C14 C14 H14A 111.2 2_475 . ? H14B C14 H14A 109.5 . . ? C17 C16 N3 109.3(2) . . ? C17 C16 H16A 125.3 . . ? N3 C16 H16A 125.3 . . ? N1 C12 N2 111.34(17) . . ? N1 C12 H9A 124.3 . . ? N2 C12 H9A 124.3 . . ? C16 C17 N4 107.0(2) . . ? C16 C17 H17A 126.5 . . ? N4 C17 H17A 126.5 . . ? N3 C15 N4 111.38(19) . . ? N3 C15 H15A 124.3 . . ? N4 C15 H15A 124.3 . . ? C10 C11 N2 106.43(18) . . ? C10 C11 H11A 126.8 . . ? N2 C11 H11A 126.8 . . ? O3 C2 C1 114.79(16) . . ? O3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? O3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C18 C19 C19 111.1(2) . 2_466 ? C18 C19 H19B 109.6 . . ? C19 C19 H19B 110.9 2_466 . ? C18 C19 H19A 109.7 . . ? C19 C19 H19A 106.0 2_466 . ? H19B C19 H19A 109.5 . . ? C11 C10 N1 108.95(17) . . ? C11 C10 H10A 125.5 . . ? N1 C10 H10A 125.5 . . ? N2 C13 C14 112.66(17) . . ? N2 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N2 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? N4 C18 C19 112.17(18) . . ? N4 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? N4 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C7 C8 C3 120.1(2) . . ? C7 C8 H8A 119.9 . . ? C3 C8 H8A 119.9 . . ? 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 O5 Zn1 O1 C1 -65.92(14) 1_565 . . . ? N1 Zn1 O1 C1 69.71(14) . . . . ? N3 Zn1 O1 C1 178.26(13) . . . . ? O5 Zn1 N1 C12 -83.37(18) 1_565 . . . ? O1 Zn1 N1 C12 148.54(16) . . . . ? N3 Zn1 N1 C12 41.61(18) . . . . ? O5 Zn1 N1 C10 99.16(18) 1_565 . . . ? O1 Zn1 N1 C10 -28.93(19) . . . . ? N3 Zn1 N1 C10 -135.86(18) . . . . ? O5 Zn1 N3 C15 -155.17(16) 1_565 . . . ? O1 Zn1 N3 C15 -38.85(18) . . . . ? N1 Zn1 N3 C15 71.30(18) . . . . ? O5 Zn1 N3 C16 26.1(2) 1_565 . . . ? O1 Zn1 N3 C16 142.45(19) . . . . ? N1 Zn1 N3 C16 -107.4(2) . . . . ? C2 O3 C3 C8 11.8(3) . . . . ? C2 O3 C3 C4 -165.01(16) . . . . ? C5 C4 C3 O3 175.74(18) . . . . ? C9 C4 C3 O3 -3.7(3) . . . . ? C5 C4 C3 C8 -1.2(3) . . . . ? C9 C4 C3 C8 179.39(18) . . . . ? Zn1 O5 C9 O4 6.7(3) 1_545 . . . ? Zn1 O5 C9 C4 -175.11(12) 1_545 . . . ? C5 C4 C9 O4 140.5(2) . . . . ? C3 C4 C9 O4 -40.1(3) . . . . ? C5 C4 C9 O5 -37.7(3) . . . . ? C3 C4 C9 O5 141.72(19) . . . . ? Zn1 O1 C1 O2 6.6(3) . . . . ? Zn1 O1 C1 C2 -169.12(15) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C9 C4 C5 C6 -179.5(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C15 N3 C16 C17 -1.0(3) . . . . ? Zn1 N3 C16 C17 177.85(18) . . . . ? C10 N1 C12 N2 0.1(2) . . . . ? Zn1 N1 C12 N2 -177.85(13) . . . . ? C11 N2 C12 N1 -0.2(2) . . . . ? C13 N2 C12 N1 -179.68(19) . . . . ? N3 C16 C17 N4 0.5(3) . . . . ? C15 N4 C17 C16 0.3(3) . . . . ? C18 N4 C17 C16 -178.9(2) . . . . ? C16 N3 C15 N4 1.2(3) . . . . ? Zn1 N3 C15 N4 -177.70(13) . . . . ? C17 N4 C15 N3 -1.0(3) . . . . ? C18 N4 C15 N3 178.18(18) . . . . ? C12 N2 C11 C10 0.2(2) . . . . ? C13 N2 C11 C10 179.7(2) . . . . ? C3 O3 C2 C1 -88.0(2) . . . . ? O2 C1 C2 O3 170.4(2) . . . . ? O1 C1 C2 O3 -13.6(3) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? N2 C11 C10 N1 -0.1(2) . . . . ? C12 N1 C10 C11 0.0(2) . . . . ? Zn1 N1 C10 C11 177.84(15) . . . . ? C12 N2 C13 C14 -127.9(2) . . . . ? C11 N2 C13 C14 52.7(3) . . . . ? C14 C14 C13 N2 -176.1(3) 2_475 . . . ? C15 N4 C18 C19 -84.1(3) . . . . ? C17 N4 C18 C19 94.9(3) . . . . ? C19 C19 C18 N4 177.0(3) 2_466 . . . ? C6 C7 C8 C3 -0.9(4) . . . . ? O3 C3 C8 C7 -175.6(2) . . . . ? C4 C3 C8 C7 1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.545 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.063 # Attachment '- cif-4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 833939' #TrackingRef '- cif-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Cd2 N4 O11' _chemical_formula_weight 819.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.572(4) _cell_length_b 17.273(7) _cell_length_c 15.536(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.170(7) _cell_angle_gamma 90.00 _cell_volume 3074(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1480 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 21.75 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.449 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_T_max 0.717 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15752 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5424 _reflns_number_gt 3244 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1081P)^2^+15.4741P] 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 5424 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1315 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2288 _refine_ls_wR_factor_gt 0.1969 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.25544(8) 0.22721(5) 0.53433(5) 0.0397(3) Uani 1 1 d . . . Cd2 Cd 0.25892(7) 0.25873(5) 0.79187(5) 0.0377(3) Uani 1 1 d . . . N1 N 0.4291(9) 0.2029(6) 0.8049(6) 0.044(2) Uani 1 1 d . . . N2 N 0.5870(9) 0.1509(6) 0.7616(6) 0.048(3) Uani 1 1 d . . . N3 N 0.9018(9) 0.3249(6) 0.7066(7) 0.053(3) Uani 1 1 d . . . N4 N 1.0808(9) 0.3097(6) 0.7713(6) 0.046(3) Uani 1 1 d . . . O1 O 0.0814(8) 0.2896(5) 0.5010(5) 0.053(2) Uani 1 1 d . . . O2 O 0.1966(8) 0.3205(5) 0.4058(5) 0.047(2) Uani 1 1 d . . . O3 O 0.0796(8) 0.3963(5) 0.2679(5) 0.053(2) Uani 1 1 d . . . O4 O 0.2047(8) 0.3258(5) 0.1615(5) 0.050(2) Uani 1 1 d . . . O5 O 0.1266(9) 0.3908(6) 0.0474(5) 0.066(3) Uani 1 1 d . . . O6 O 0.4103(8) 0.3031(5) 0.5697(5) 0.057(2) Uani 1 1 d . . . O7 O 0.3033(8) 0.3310(5) 0.6719(5) 0.051(2) Uani 1 1 d . . . O8 O 0.4446(8) 0.3954(5) 0.8110(5) 0.055(2) Uani 1 1 d . . . O9 O 0.3142(8) 0.3319(5) 0.9177(5) 0.051(2) Uani 1 1 d . . . O10 O 0.4204(9) 0.3836(6) 1.0334(5) 0.067(3) Uani 1 1 d . . . C1 C 0.1027(11) 0.3278(7) 0.4368(7) 0.041(3) Uani 1 1 d . . . C2 C 0.0142(10) 0.3883(6) 0.4015(7) 0.039(3) Uani 1 1 d . . . C3 C -0.0624(11) 0.4142(8) 0.4581(8) 0.051(3) Uani 1 1 d . . . H3 H -0.0588 0.3911 0.5125 0.062 Uiso 1 1 calc R . . C4 C -0.1431(12) 0.4729(8) 0.4358(9) 0.059(4) Uani 1 1 d . . . H4 H -0.1954 0.4875 0.4731 0.071 Uiso 1 1 calc R . . C5 C -0.1432(12) 0.5089(8) 0.3564(9) 0.057(4) Uani 1 1 d . . . H5 H -0.1933 0.5504 0.3414 0.068 Uiso 1 1 calc R . . C6 C -0.0693(11) 0.4842(7) 0.2982(9) 0.053(3) Uani 1 1 d . . . H6 H -0.0731 0.5074 0.2438 0.063 Uiso 1 1 calc R . . C7 C 0.0098(11) 0.4249(7) 0.3218(8) 0.044(3) Uani 1 1 d . . . C8 C 0.0629(12) 0.4252(7) 0.1792(7) 0.046(3) Uani 1 1 d . . . H8A H 0.0855 0.4792 0.1786 0.056 Uiso 1 1 calc R . . H8B H -0.0187 0.4211 0.1546 0.056 Uiso 1 1 calc R . . C9 C 0.1367(11) 0.3780(7) 0.1259(7) 0.043(3) Uani 1 1 d . . . C10 C 0.3920(11) 0.3421(7) 0.6357(7) 0.041(3) Uani 1 1 d . . . C11 C 0.4770(10) 0.4051(6) 0.6636(7) 0.037(3) Uani 1 1 d . . . C12 C 0.5026(11) 0.4295(7) 0.7504(8) 0.046(3) Uani 1 1 d . . . C13 C 0.5884(11) 0.4850(7) 0.7721(8) 0.049(3) Uani 1 1 d . . . H13 H 0.6091 0.4999 0.8297 0.059 Uiso 1 1 calc R . . C14 C 0.6433(12) 0.5184(8) 0.7073(10) 0.062(4) Uani 1 1 d . . . H14 H 0.6998 0.5564 0.7219 0.074 Uiso 1 1 calc R . . C15 C 0.6152(13) 0.4961(8) 0.6211(9) 0.056(4) Uani 1 1 d . . . H15 H 0.6495 0.5198 0.5773 0.067 Uiso 1 1 calc R . . C16 C 0.5362(12) 0.4385(7) 0.6029(8) 0.051(3) Uani 1 1 d . . . H16 H 0.5213 0.4205 0.5459 0.061 Uiso 1 1 calc R . . C17 C 0.4750(13) 0.4171(9) 0.8979(8) 0.061(4) Uani 1 1 d . . . H17A H 0.4651 0.4725 0.9040 0.073 Uiso 1 1 calc R . . H17B H 0.5561 0.4044 0.9175 0.073 Uiso 1 1 calc R . . C18 C 0.3972(12) 0.3743(7) 0.9516(8) 0.048(3) Uani 1 1 d . . . C19 C 0.4795(11) 0.1768(7) 0.7393(8) 0.042(3) Uani 1 1 d . . . H19 H 0.4423 0.1767 0.6822 0.051 Uiso 1 1 calc R . . C20 C 0.5125(12) 0.1924(8) 0.8759(8) 0.057(4) Uani 1 1 d . . . H20 H 0.5040 0.2052 0.9328 0.068 Uiso 1 1 calc R . . C21 C 0.6112(13) 0.1599(8) 0.8502(8) 0.063(4) Uani 1 1 d . . . H21 H 0.6800 0.1467 0.8857 0.076 Uiso 1 1 calc R . . C22 C 0.6644(11) 0.1237(8) 0.7002(9) 0.056(4) Uani 1 1 d . . . H22A H 0.6189 0.1153 0.6436 0.067 Uiso 1 1 calc R . . H22B H 0.6994 0.0748 0.7204 0.067 Uiso 1 1 calc R . . C23 C 0.7613(12) 0.1833(8) 0.6919(10) 0.061(4) Uani 1 1 d . . . H23A H 0.8124 0.1873 0.7470 0.073 Uiso 1 1 calc R . . H23B H 0.8077 0.1659 0.6483 0.073 Uiso 1 1 calc R . . C24 C 0.7098(12) 0.2618(8) 0.6666(11) 0.070(4) Uani 1 1 d . . . H24A H 0.6773 0.2836 0.7155 0.084 Uiso 1 1 calc R . . H24B H 0.6466 0.2557 0.6190 0.084 Uiso 1 1 calc R . . C25 C 0.8001(11) 0.3179(8) 0.6392(10) 0.064(4) Uani 1 1 d . . . H25A H 0.8252 0.2997 0.5858 0.076 Uiso 1 1 calc R . . H25B H 0.7646 0.3685 0.6280 0.076 Uiso 1 1 calc R . . C26 C 1.0102(12) 0.3029(8) 0.6986(8) 0.051(3) Uani 1 1 d . . . H26 H 1.0326 0.2847 0.6471 0.061 Uiso 1 1 calc R . . C27 C 1.0140(13) 0.3381(8) 0.8304(9) 0.059(4) Uani 1 1 d . . . H27 H 1.0404 0.3488 0.8886 0.071 Uiso 1 1 calc R . . C28 C 0.9061(13) 0.3478(8) 0.7914(10) 0.061(4) Uani 1 1 d . . . H28 H 0.8439 0.3668 0.8169 0.073 Uiso 1 1 calc R . . O11 O 0.851(3) 0.4467(14) -0.0052(18) 0.151(14) Uani 0.50 1 d P . . O12 O 0.856(4) 0.196(2) 0.492(2) 0.198(19) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0394(6) 0.0470(6) 0.0332(5) -0.0006(4) 0.0070(4) 0.0005(4) Cd2 0.0309(5) 0.0478(6) 0.0349(5) 0.0068(4) 0.0060(4) 0.0047(4) N1 0.044(6) 0.043(6) 0.044(6) 0.002(5) 0.011(5) 0.004(5) N2 0.030(6) 0.066(7) 0.049(6) 0.005(5) 0.011(5) 0.006(5) N3 0.028(6) 0.065(7) 0.066(7) 0.010(6) 0.006(6) 0.006(5) N4 0.049(7) 0.055(7) 0.036(6) 0.008(5) 0.013(5) 0.008(5) O1 0.057(6) 0.063(6) 0.041(5) 0.015(4) 0.011(4) 0.005(4) O2 0.047(5) 0.057(6) 0.041(5) -0.005(4) 0.019(4) 0.007(4) O3 0.062(6) 0.058(6) 0.041(5) 0.004(4) 0.018(4) 0.016(4) O4 0.053(6) 0.056(6) 0.043(5) 0.010(4) 0.010(4) 0.011(4) O5 0.087(8) 0.077(7) 0.032(5) 0.012(4) 0.002(5) 0.017(5) O6 0.060(6) 0.064(6) 0.051(5) -0.017(5) 0.018(5) -0.009(5) O7 0.053(6) 0.052(5) 0.048(5) 0.004(4) 0.010(5) -0.001(4) O8 0.068(7) 0.070(6) 0.030(4) -0.012(4) 0.013(4) -0.028(5) O9 0.051(6) 0.057(6) 0.045(5) -0.009(4) 0.008(4) -0.013(4) O10 0.082(8) 0.083(7) 0.038(5) 0.001(5) 0.008(5) -0.020(6) C1 0.037(8) 0.051(7) 0.036(6) -0.007(5) 0.009(6) 0.007(5) C2 0.042(8) 0.032(6) 0.041(7) 0.000(5) 0.002(6) -0.008(5) C3 0.051(9) 0.060(9) 0.043(7) 0.000(6) 0.008(6) 0.001(6) C4 0.042(9) 0.072(10) 0.068(9) 0.000(8) 0.026(7) 0.011(7) C5 0.049(9) 0.048(8) 0.076(10) -0.002(7) 0.014(8) 0.007(6) C6 0.054(9) 0.048(8) 0.058(8) -0.002(6) 0.011(7) 0.011(6) C7 0.041(8) 0.046(7) 0.043(7) -0.013(6) 0.005(6) 0.005(6) C8 0.057(9) 0.056(8) 0.030(6) 0.002(5) 0.017(6) -0.001(6) C9 0.056(9) 0.040(7) 0.032(6) -0.002(5) 0.006(6) -0.008(6) C10 0.049(8) 0.038(7) 0.036(6) 0.007(5) 0.007(6) 0.002(6) C11 0.042(8) 0.039(7) 0.031(6) 0.004(5) 0.008(5) 0.002(5) C12 0.042(8) 0.060(8) 0.037(6) -0.008(6) 0.003(6) 0.002(6) C13 0.059(9) 0.044(7) 0.042(7) -0.016(6) 0.001(6) -0.010(6) C14 0.049(9) 0.054(9) 0.089(11) 0.001(8) 0.033(8) -0.006(6) C15 0.064(10) 0.052(8) 0.057(9) 0.008(7) 0.023(7) 0.004(7) C16 0.064(10) 0.047(8) 0.046(7) 0.000(6) 0.019(7) 0.009(7) C17 0.069(10) 0.079(10) 0.037(7) -0.001(7) 0.012(7) -0.018(8) C18 0.057(9) 0.054(8) 0.033(7) 0.001(6) 0.010(6) 0.004(7) C19 0.044(8) 0.045(7) 0.038(7) 0.006(5) 0.006(6) -0.003(6) C20 0.058(10) 0.075(10) 0.035(7) -0.003(6) -0.003(7) 0.012(7) C21 0.060(10) 0.080(10) 0.044(8) -0.003(7) -0.012(7) 0.014(8) C22 0.045(8) 0.059(9) 0.068(9) 0.001(7) 0.017(7) 0.011(6) C23 0.052(9) 0.065(9) 0.069(9) 0.007(7) 0.018(8) 0.012(7) C24 0.034(8) 0.074(10) 0.096(11) 0.026(9) -0.012(8) -0.002(7) C25 0.040(8) 0.073(10) 0.076(10) 0.026(8) 0.002(7) -0.003(7) C26 0.056(9) 0.063(9) 0.034(7) 0.017(6) 0.010(6) 0.006(7) C27 0.062(10) 0.060(9) 0.059(9) -0.008(7) 0.017(8) 0.017(7) C28 0.050(10) 0.065(10) 0.074(10) 0.003(8) 0.032(8) 0.015(7) O11 0.25(4) 0.066(16) 0.11(2) 0.042(15) -0.06(2) -0.05(2) O12 0.28(5) 0.20(4) 0.16(3) -0.01(3) 0.17(4) -0.01(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O6 2.226(9) . ? Cd1 O9 2.267(8) 4_565 ? Cd1 O1 2.278(9) . ? Cd1 O4 2.328(8) 4_566 ? Cd1 O5 2.550(10) 4_566 ? Cd1 O2 2.580(8) . ? Cd2 N1 2.176(10) . ? Cd2 N4 2.222(10) 1_455 ? Cd2 O9 2.339(8) . ? Cd2 O7 2.360(8) . ? Cd2 O2 2.426(8) 4_566 ? Cd2 O4 2.503(8) 4_566 ? N1 C19 1.324(14) . ? N1 C20 1.371(15) . ? N2 C19 1.321(15) . ? N2 C21 1.374(15) . ? N2 C22 1.475(15) . ? N3 C26 1.334(16) . ? N3 C28 1.368(17) . ? N3 C25 1.465(17) . ? N4 C26 1.302(15) . ? N4 C27 1.374(15) . ? N4 Cd2 2.222(10) 1_655 ? O1 C1 1.248(13) . ? O2 C1 1.256(13) . ? O2 Cd2 2.426(8) 4_565 ? O3 C7 1.339(13) . ? O3 C8 1.451(13) . ? O4 C9 1.270(14) . ? O4 Cd1 2.328(8) 4_565 ? O4 Cd2 2.503(8) 4_565 ? O5 C9 1.228(13) . ? O5 Cd1 2.550(10) 4_565 ? O6 C10 1.270(13) . ? O7 C10 1.253(14) . ? O8 C12 1.366(14) . ? O8 C17 1.397(14) . ? O9 C18 1.263(15) . ? O9 Cd1 2.267(8) 4_566 ? O10 C18 1.270(14) . ? C1 C2 1.511(16) . ? C2 C7 1.385(16) . ? C2 C3 1.408(16) . ? C3 C4 1.389(18) . ? C3 H3 0.9300 . ? C4 C5 1.381(18) . ? C4 H4 0.9300 . ? C5 C6 1.396(16) . ? C5 H5 0.9300 . ? C6 C7 1.388(17) . ? C6 H6 0.9300 . ? C8 C9 1.510(16) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C11 1.490(16) . ? C11 C16 1.370(16) . ? C11 C12 1.403(15) . ? C12 C13 1.387(17) . ? C13 C14 1.390(17) . ? C13 H13 0.9300 . ? C14 C15 1.387(19) . ? C14 H14 0.9300 . ? C15 C16 1.354(18) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.506(17) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C19 H19 0.9300 . ? C20 C21 1.381(18) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.541(18) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.511(18) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.530(18) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26 0.9300 . ? C27 C28 1.318(19) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Cd1 O9 98.1(3) . 4_565 ? O6 Cd1 O1 115.6(3) . . ? O9 Cd1 O1 112.8(3) 4_565 . ? O6 Cd1 O4 108.3(3) . 4_566 ? O9 Cd1 O4 129.9(3) 4_565 4_566 ? O1 Cd1 O4 93.3(3) . 4_566 ? O6 Cd1 O5 155.6(3) . 4_566 ? O9 Cd1 O5 87.1(3) 4_565 4_566 ? O1 Cd1 O5 83.6(3) . 4_566 ? O4 Cd1 O5 52.9(3) 4_566 4_566 ? O6 Cd1 O2 86.4(3) . . ? O9 Cd1 O2 74.8(3) 4_565 . ? O1 Cd1 O2 53.2(3) . . ? O4 Cd1 O2 146.3(3) 4_566 . ? O5 Cd1 O2 117.9(3) 4_566 . ? N1 Cd2 N4 176.0(4) . 1_455 ? N1 Cd2 O9 91.4(3) . . ? N4 Cd2 O9 92.5(3) 1_455 . ? N1 Cd2 O7 90.7(3) . . ? N4 Cd2 O7 88.7(3) 1_455 . ? O9 Cd2 O7 108.0(3) . . ? N1 Cd2 O2 92.3(3) . 4_566 ? N4 Cd2 O2 87.9(3) 1_455 4_566 ? O9 Cd2 O2 76.6(3) . 4_566 ? O7 Cd2 O2 174.3(3) . 4_566 ? N1 Cd2 O4 86.4(3) . 4_566 ? N4 Cd2 O4 89.6(3) 1_455 4_566 ? O9 Cd2 O4 176.9(3) . 4_566 ? O7 Cd2 O4 74.2(3) . 4_566 ? O2 Cd2 O4 101.2(3) 4_566 4_566 ? C19 N1 C20 103.7(10) . . ? C19 N1 Cd2 124.8(8) . . ? C20 N1 Cd2 131.2(8) . . ? C19 N2 C21 105.9(11) . . ? C19 N2 C22 125.0(11) . . ? C21 N2 C22 128.9(11) . . ? C26 N3 C28 105.4(11) . . ? C26 N3 C25 125.4(12) . . ? C28 N3 C25 128.9(12) . . ? C26 N4 C27 105.6(11) . . ? C26 N4 Cd2 123.0(8) . 1_655 ? C27 N4 Cd2 130.1(9) . 1_655 ? C1 O1 Cd1 99.4(7) . . ? C1 O2 Cd2 134.4(8) . 4_565 ? C1 O2 Cd1 85.0(7) . . ? Cd2 O2 Cd1 98.0(3) 4_565 . ? C7 O3 C8 117.1(9) . . ? C9 O4 Cd1 97.1(7) . 4_565 ? C9 O4 Cd2 146.6(8) . 4_565 ? Cd1 O4 Cd2 113.1(3) 4_565 4_565 ? C9 O5 Cd1 87.8(8) . 4_565 ? C10 O6 Cd1 106.9(8) . . ? C10 O7 Cd2 136.0(8) . . ? C12 O8 C17 118.1(9) . . ? C18 O9 Cd1 102.9(7) . 4_566 ? C18 O9 Cd2 139.8(8) . . ? Cd1 O9 Cd2 110.4(3) 4_566 . ? O1 C1 O2 122.2(11) . . ? O1 C1 C2 117.0(11) . . ? O2 C1 C2 120.6(11) . . ? C7 C2 C3 117.9(11) . . ? C7 C2 C1 125.3(11) . . ? C3 C2 C1 116.5(10) . . ? C4 C3 C2 122.4(12) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C5 C4 C3 117.9(12) . . ? C5 C4 H4 121.1 . . ? C3 C4 H4 121.1 . . ? C4 C5 C6 121.2(13) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 119.7(12) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O3 C7 C2 116.2(11) . . ? O3 C7 C6 122.8(11) . . ? C2 C7 C6 120.9(12) . . ? O3 C8 C9 109.0(10) . . ? O3 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? O3 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O5 C9 O4 121.7(12) . . ? O5 C9 C8 117.8(11) . . ? O4 C9 C8 120.4(10) . . ? O7 C10 O6 121.5(11) . . ? O7 C10 C11 122.0(11) . . ? O6 C10 C11 116.3(11) . . ? C16 C11 C12 118.5(12) . . ? C16 C11 C10 118.8(11) . . ? C12 C11 C10 122.6(11) . . ? O8 C12 C13 122.4(11) . . ? O8 C12 C11 118.4(11) . . ? C13 C12 C11 119.2(12) . . ? C12 C13 C14 119.7(12) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 121.0(13) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 117.8(13) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? C15 C16 C11 123.6(12) . . ? C15 C16 H16 118.2 . . ? C11 C16 H16 118.2 . . ? O8 C17 C18 108.4(11) . . ? O8 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O8 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? O9 C18 O10 122.1(12) . . ? O9 C18 C17 122.2(11) . . ? O10 C18 C17 115.7(12) . . ? N2 C19 N1 114.5(11) . . ? N2 C19 H19 122.7 . . ? N1 C19 H19 122.7 . . ? N1 C20 C21 109.7(11) . . ? N1 C20 H20 125.1 . . ? C21 C20 H20 125.1 . . ? N2 C21 C20 106.1(11) . . ? N2 C21 H21 127.0 . . ? C20 C21 H21 127.0 . . ? N2 C22 C23 111.0(11) . . ? N2 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? N2 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C22 110.8(11) . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C25 112.4(12) . . ? C23 C24 H24A 109.1 . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24B 109.1 . . ? C25 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? N3 C25 C24 111.4(11) . . ? N3 C25 H25A 109.4 . . ? C24 C25 H25A 109.4 . . ? N3 C25 H25B 109.4 . . ? C24 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? N4 C26 N3 112.1(11) . . ? N4 C26 H26 123.9 . . ? N3 C26 H26 123.9 . . ? C28 C27 N4 108.9(13) . . ? C28 C27 H27 125.6 . . ? N4 C27 H27 125.6 . . ? C27 C28 N3 108.0(12) . . ? C27 C28 H28 126.0 . . ? N3 C28 H28 126.0 . . ? 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 Cd2 N1 C19 40(5) 1_455 . . . ? O9 Cd2 N1 C19 -150.6(10) . . . . ? O7 Cd2 N1 C19 -42.6(10) . . . . ? O2 Cd2 N1 C19 132.7(10) 4_566 . . . ? O4 Cd2 N1 C19 31.6(10) 4_566 . . . ? N4 Cd2 N1 C20 -147(5) 1_455 . . . ? O9 Cd2 N1 C20 22.5(12) . . . . ? O7 Cd2 N1 C20 130.6(11) . . . . ? O2 Cd2 N1 C20 -54.2(12) 4_566 . . . ? O4 Cd2 N1 C20 -155.3(12) 4_566 . . . ? O6 Cd1 O1 C1 61.2(8) . . . . ? O9 Cd1 O1 C1 -50.5(8) 4_565 . . . ? O4 Cd1 O1 C1 173.3(7) 4_566 . . . ? O5 Cd1 O1 C1 -134.6(7) 4_566 . . . ? O2 Cd1 O1 C1 -2.4(7) . . . . ? O6 Cd1 O2 C1 -123.6(7) . . . . ? O9 Cd1 O2 C1 137.0(7) 4_565 . . . ? O1 Cd1 O2 C1 2.3(6) . . . . ? O4 Cd1 O2 C1 -5.4(9) 4_566 . . . ? O5 Cd1 O2 C1 58.7(7) 4_566 . . . ? O6 Cd1 O2 Cd2 102.2(3) . . . 4_565 ? O9 Cd1 O2 Cd2 2.8(3) 4_565 . . 4_565 ? O1 Cd1 O2 Cd2 -131.9(5) . . . 4_565 ? O4 Cd1 O2 Cd2 -139.6(4) 4_566 . . 4_565 ? O5 Cd1 O2 Cd2 -75.5(4) 4_566 . . 4_565 ? O9 Cd1 O6 C10 179.6(7) 4_565 . . . ? O1 Cd1 O6 C10 59.6(8) . . . . ? O4 Cd1 O6 C10 -43.5(8) 4_566 . . . ? O5 Cd1 O6 C10 -79.5(11) 4_566 . . . ? O2 Cd1 O6 C10 105.5(8) . . . . ? N1 Cd2 O7 C10 -8.2(11) . . . . ? N4 Cd2 O7 C10 175.8(11) 1_455 . . . ? O9 Cd2 O7 C10 83.5(11) . . . . ? O2 Cd2 O7 C10 -131(3) 4_566 . . . ? O4 Cd2 O7 C10 -94.2(11) 4_566 . . . ? N1 Cd2 O9 C18 48.7(13) . . . . ? N4 Cd2 O9 C18 -132.0(13) 1_455 . . . ? O7 Cd2 O9 C18 -42.5(14) . . . . ? O2 Cd2 O9 C18 140.8(13) 4_566 . . . ? O4 Cd2 O9 C18 93(5) 4_566 . . . ? N1 Cd2 O9 Cd1 -95.3(4) . . . 4_566 ? N4 Cd2 O9 Cd1 83.9(4) 1_455 . . 4_566 ? O7 Cd2 O9 Cd1 173.4(3) . . . 4_566 ? O2 Cd2 O9 Cd1 -3.3(3) 4_566 . . 4_566 ? O4 Cd2 O9 Cd1 -51(5) 4_566 . . 4_566 ? Cd1 O1 C1 O2 4.6(13) . . . . ? Cd1 O1 C1 C2 -170.9(8) . . . . ? Cd2 O2 C1 O1 92.3(13) 4_565 . . . ? Cd1 O2 C1 O1 -4.1(11) . . . . ? Cd2 O2 C1 C2 -92.3(13) 4_565 . . . ? Cd1 O2 C1 C2 171.3(10) . . . . ? O1 C1 C2 C7 -166.1(11) . . . . ? O2 C1 C2 C7 18.3(18) . . . . ? O1 C1 C2 C3 20.2(16) . . . . ? O2 C1 C2 C3 -155.4(11) . . . . ? C7 C2 C3 C4 1.8(19) . . . . ? C1 C2 C3 C4 176.0(12) . . . . ? C2 C3 C4 C5 -3(2) . . . . ? C3 C4 C5 C6 4(2) . . . . ? C4 C5 C6 C7 -3(2) . . . . ? C8 O3 C7 C2 170.2(10) . . . . ? C8 O3 C7 C6 -5.2(18) . . . . ? C3 C2 C7 O3 -176.7(11) . . . . ? C1 C2 C7 O3 9.7(17) . . . . ? C3 C2 C7 C6 -1.2(18) . . . . ? C1 C2 C7 C6 -174.8(12) . . . . ? C5 C6 C7 O3 177.1(12) . . . . ? C5 C6 C7 C2 1.9(19) . . . . ? C7 O3 C8 C9 -171.8(10) . . . . ? Cd1 O5 C9 O4 6.4(12) 4_565 . . . ? Cd1 O5 C9 C8 -172.1(10) 4_565 . . . ? Cd1 O4 C9 O5 -7.1(14) 4_565 . . . ? Cd2 O4 C9 O5 -162.5(10) 4_565 . . . ? Cd1 O4 C9 C8 171.4(10) 4_565 . . . ? Cd2 O4 C9 C8 16(2) 4_565 . . . ? O3 C8 C9 O5 174.7(11) . . . . ? O3 C8 C9 O4 -3.9(16) . . . . ? Cd2 O7 C10 O6 95.9(13) . . . . ? Cd2 O7 C10 C11 -88.5(14) . . . . ? Cd1 O6 C10 O7 4.1(13) . . . . ? Cd1 O6 C10 C11 -171.7(8) . . . . ? O7 C10 C11 C16 -149.5(12) . . . . ? O6 C10 C11 C16 26.3(16) . . . . ? O7 C10 C11 C12 33.4(17) . . . . ? O6 C10 C11 C12 -150.8(12) . . . . ? C17 O8 C12 C13 -1.0(19) . . . . ? C17 O8 C12 C11 176.7(12) . . . . ? C16 C11 C12 O8 -179.1(11) . . . . ? C10 C11 C12 O8 -2.0(18) . . . . ? C16 C11 C12 C13 -1.3(18) . . . . ? C10 C11 C12 C13 175.8(12) . . . . ? O8 C12 C13 C14 -179.1(12) . . . . ? C11 C12 C13 C14 3(2) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C13 C14 C15 C16 -3(2) . . . . ? C14 C15 C16 C11 5(2) . . . . ? C12 C11 C16 C15 -3(2) . . . . ? C10 C11 C16 C15 180.0(12) . . . . ? C12 O8 C17 C18 178.1(11) . . . . ? Cd1 O9 C18 O10 -8.5(15) 4_566 . . . ? Cd2 O9 C18 O10 -154.1(10) . . . . ? Cd1 O9 C18 C17 171.5(11) 4_566 . . . ? Cd2 O9 C18 C17 26(2) . . . . ? O8 C17 C18 O9 -5.2(19) . . . . ? O8 C17 C18 O10 174.8(12) . . . . ? C21 N2 C19 N1 0.4(15) . . . . ? C22 N2 C19 N1 -175.8(11) . . . . ? C20 N1 C19 N2 -0.2(14) . . . . ? Cd2 N1 C19 N2 174.6(8) . . . . ? C19 N1 C20 C21 -0.1(15) . . . . ? Cd2 N1 C20 C21 -174.3(9) . . . . ? C19 N2 C21 C20 -0.4(16) . . . . ? C22 N2 C21 C20 175.5(12) . . . . ? N1 C20 C21 N2 0.3(17) . . . . ? C19 N2 C22 C23 106.4(14) . . . . ? C21 N2 C22 C23 -68.8(17) . . . . ? N2 C22 C23 C24 -55.2(16) . . . . ? C22 C23 C24 C25 -168.0(13) . . . . ? C26 N3 C25 C24 115.2(15) . . . . ? C28 N3 C25 C24 -58.3(19) . . . . ? C23 C24 C25 N3 -54.7(18) . . . . ? C27 N4 C26 N3 0.0(15) . . . . ? Cd2 N4 C26 N3 168.1(8) 1_655 . . . ? C28 N3 C26 N4 0.4(15) . . . . ? C25 N3 C26 N4 -174.4(11) . . . . ? C26 N4 C27 C28 -0.4(15) . . . . ? Cd2 N4 C27 C28 -167.3(10) 1_655 . . . ? N4 C27 C28 N3 0.6(17) . . . . ? C26 N3 C28 C27 -0.6(16) . . . . ? C25 N3 C28 C27 173.9(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 3.467 _refine_diff_density_min -1.057 _refine_diff_density_rms 0.189