# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Wu, Chuan-De' _publ_contact_author_email cdwu@zju.edu.cn loop_ _publ_author_name 'Xiu-Li Yang' 'Ming-Hua Xie' 'Chao Zou' 'Fei-Fei Sun' 'Chuan-De Wu' data_AspCd _database_code_depnum_ccdc_archive 'CCDC 793341' #TrackingRef '- AspCd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 Cd2 N4 O12' _chemical_formula_weight 741.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd 0.1185 4.6533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.56670(10) _cell_length_b 16.4081(2) _cell_length_c 16.4469(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2581.69(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9615 _cell_measurement_theta_min 3.81 _cell_measurement_theta_max 67.04 _exptl_crystal_description bloc _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.907 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 13.814 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.106 _exptl_absorpt_correction_T_max 0.166 _exptl_absorpt_process_details CrysAlisPro _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 9615 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 67.04 _reflns_number_total 4270 _reflns_number_gt 4008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0319P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(7) _refine_ls_number_reflns 4270 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0567 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd -0.02557(3) -0.429643(17) -0.120793(17) 0.01002(8) Uani 1 1 d . . . Cd2 Cd 0.31557(3) -0.749880(19) 0.148950(15) 0.00979(7) Uani 1 1 d . . . O1 O 0.8662(3) -0.61153(19) -0.1237(2) 0.0171(7) Uani 1 1 d . . . O2 O 0.7899(3) -0.4969(2) -0.0669(2) 0.0191(7) Uani 1 1 d . . . O3 O 0.5393(3) -0.69733(18) 0.14215(17) 0.0152(6) Uani 1 1 d . . . O4 O 0.4449(3) -0.7191(2) 0.02219(19) 0.0199(8) Uani 1 1 d . . . O5 O -0.1569(3) -0.31636(19) -0.07911(19) 0.0151(7) Uani 1 1 d . . . O6 O -0.1190(3) -0.18460(19) -0.0493(2) 0.0178(7) Uani 1 1 d . . . O7 O 0.0997(3) -0.32983(19) -0.19453(17) 0.0145(7) Uani 1 1 d . . . O8 O 0.1871(4) -0.20777(19) -0.22331(18) 0.0170(7) Uani 1 1 d . . . O9 O -0.1464(3) -0.4175(2) -0.24152(17) 0.0169(7) Uani 1 1 d . . . H9A H -0.1696 -0.4556 -0.2656 0.020 Uiso 1 1 d . . . H9B H -0.1200 -0.3840 -0.2735 0.020 Uiso 1 1 d . . . OW1 O -0.1901(4) -0.5478(2) -0.3317(2) 0.0299(8) Uani 1 1 d . . . HW1A H -0.1248 -0.5478 -0.3766 0.036 Uiso 1 1 d . . . HW1B H -0.1930 -0.6089 -0.3265 0.036 Uiso 1 1 d . . . OW2 O -0.4486(4) -0.4465(2) 0.0241(2) 0.0223(8) Uani 1 1 d . . . HW2A H -0.5116 -0.4020 0.0259 0.027 Uiso 1 1 d . . . HW2B H -0.4044 -0.4337 -0.0185 0.027 Uiso 1 1 d . . . OW3 O -0.3865(4) -0.3131(3) -0.1904(3) 0.0462(12) Uani 1 1 d . . . HW3A H -0.3334 -0.3557 -0.2243 0.055 Uiso 1 1 d . . . HW3B H -0.3111 -0.3037 -0.1490 0.055 Uiso 1 1 d . . . N1 N 0.6059(4) -0.6794(2) -0.1170(2) 0.0097(7) Uani 1 1 d . . . H1A H 0.5253 -0.7023 -0.0937 0.012 Uiso 1 1 d . . . N2 N 0.1695(4) -0.5097(2) -0.1524(2) 0.0172(8) Uani 1 1 d . . . N3 N 0.0875(4) -0.3653(2) -0.0084(2) 0.0115(8) Uani 1 1 d . . . H3A H 0.1827 -0.3691 -0.0006 0.014 Uiso 1 1 d . . . N4 N 0.2044(4) -0.6243(2) 0.1356(2) 0.0159(8) Uani 1 1 d . . . C1 C 0.7762(4) -0.5717(3) -0.0851(2) 0.0100(8) Uani 1 1 d . . . C2 C 0.6425(4) -0.6152(3) -0.0572(2) 0.0101(9) Uani 1 1 d . . . H2A H 0.5659 -0.5758 -0.0530 0.012 Uiso 1 1 calc R . . C3 C 0.6695(5) -0.6543(3) 0.0267(2) 0.0139(9) Uani 1 1 d . . . H3B H 0.7415 -0.6955 0.0208 0.017 Uiso 1 1 calc R . . H3C H 0.7052 -0.6127 0.0631 0.017 Uiso 1 1 calc R . . C4 C 0.5439(5) -0.6927(3) 0.0649(3) 0.0131(9) Uani 1 1 d . . . C5 C 0.5492(5) -0.6452(3) -0.1945(2) 0.0144(9) Uani 1 1 d . . . H5A H 0.5308 -0.6895 -0.2319 0.017 Uiso 1 1 calc R . . H5B H 0.6193 -0.6102 -0.2190 0.017 Uiso 1 1 calc R . . C6 C 0.2936(5) -0.4722(3) -0.1566(3) 0.0170(10) Uani 1 1 d . . . H6A H 0.2963 -0.4160 -0.1493 0.020 Uiso 1 1 calc R . . C7 C 0.4185(5) -0.5126(3) -0.1712(3) 0.0164(10) Uani 1 1 d . . . H7A H 0.5023 -0.4840 -0.1736 0.020 Uiso 1 1 calc R . . C8 C 0.4165(4) -0.5968(3) -0.1823(3) 0.0112(9) Uani 1 1 d . . . C9 C 0.2878(5) -0.6344(3) -0.1804(3) 0.0233(11) Uani 1 1 d . . . H9C H 0.2819 -0.6904 -0.1887 0.028 Uiso 1 1 calc R . . C10 C 0.1683(5) -0.5905(3) -0.1664(3) 0.0263(12) Uani 1 1 d . . . H10A H 0.0830 -0.6177 -0.1665 0.032 Uiso 1 1 calc R . . C11 C -0.0824(4) -0.2578(3) -0.0533(2) 0.0126(9) Uani 1 1 d . . . C12 C 0.0660(5) -0.2773(3) -0.0237(2) 0.0102(9) Uani 1 1 d . . . H12A H 0.0799 -0.2487 0.0280 0.012 Uiso 1 1 calc R . . C13 C 0.1729(4) -0.2434(3) -0.0845(2) 0.0118(8) Uani 1 1 d . . . H13A H 0.1760 -0.1847 -0.0782 0.014 Uiso 1 1 calc R . . H13B H 0.2643 -0.2644 -0.0699 0.014 Uiso 1 1 calc R . . C14 C 0.1477(4) -0.2622(3) -0.1729(2) 0.0096(9) Uani 1 1 d . . . C15 C 0.0337(5) -0.3900(3) 0.0723(2) 0.0165(9) Uani 1 1 d . . . H15A H -0.0676 -0.3924 0.0706 0.020 Uiso 1 1 calc R . . H15B H 0.0602 -0.3496 0.1125 0.020 Uiso 1 1 calc R . . C16 C 0.0683(6) -0.6144(3) 0.1194(4) 0.0373(14) Uani 1 1 d . . . H16A H 0.0104 -0.6599 0.1213 0.045 Uiso 1 1 calc R . . C17 C 0.0096(6) -0.5406(3) 0.1000(4) 0.0340(14) Uani 1 1 d . . . H17A H -0.0856 -0.5373 0.0891 0.041 Uiso 1 1 calc R . . C18 C 0.0908(5) -0.4717(3) 0.0967(2) 0.0125(9) Uani 1 1 d . . . C19 C 0.2316(5) -0.4801(3) 0.1168(3) 0.0219(11) Uani 1 1 d . . . H19A H 0.2904 -0.4350 0.1176 0.026 Uiso 1 1 calc R . . C20 C 0.2823(5) -0.5572(3) 0.1358(3) 0.0197(10) Uani 1 1 d . . . H20A H 0.3763 -0.5621 0.1495 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01200(14) 0.00621(13) 0.01185(12) -0.00126(11) 0.00153(11) -0.00045(12) Cd2 0.01153(13) 0.00750(14) 0.01033(12) 0.00188(12) -0.00041(10) -0.00159(14) O1 0.0171(15) 0.0130(16) 0.0211(15) -0.0040(14) 0.0055(14) -0.0029(13) O2 0.0225(19) 0.0123(17) 0.0225(17) -0.0028(13) 0.0072(14) -0.0073(14) O3 0.0177(15) 0.0169(16) 0.0110(14) 0.0031(12) 0.0017(13) -0.0034(14) O4 0.0175(17) 0.029(2) 0.0133(14) -0.0022(13) 0.0028(12) -0.0091(14) O5 0.0170(17) 0.0097(16) 0.0187(15) -0.0011(12) -0.0016(13) -0.0006(13) O6 0.0188(17) 0.0066(17) 0.0280(18) 0.0040(14) 0.0037(14) 0.0030(14) O7 0.0201(16) 0.0125(17) 0.0110(15) -0.0001(12) -0.0026(13) -0.0030(14) O8 0.0274(17) 0.0113(16) 0.0122(14) 0.0002(12) 0.0036(14) -0.0040(15) O9 0.0206(17) 0.0165(18) 0.0137(14) -0.0028(13) -0.0003(12) -0.0059(14) OW1 0.050(2) 0.0120(18) 0.0273(19) -0.0053(14) 0.0037(18) 0.0013(17) OW2 0.032(2) 0.0123(18) 0.0231(16) -0.0034(13) 0.0062(14) 0.0014(15) OW3 0.035(2) 0.053(3) 0.051(3) -0.012(2) -0.015(2) 0.012(2) N1 0.0133(17) 0.0069(18) 0.0088(15) -0.0020(15) 0.0009(15) -0.0034(14) N2 0.019(2) 0.0085(19) 0.0243(19) 0.0021(16) 0.0025(18) 0.0015(16) N3 0.0139(18) 0.008(2) 0.0125(17) 0.0009(14) 0.0029(15) 0.0006(15) N4 0.018(2) 0.0076(19) 0.022(2) 0.0034(14) -0.0043(16) -0.0008(16) C1 0.015(2) 0.009(2) 0.0061(17) 0.0011(18) -0.0016(15) -0.0032(19) C2 0.013(2) 0.009(2) 0.0085(19) 0.0007(16) 0.0020(16) 0.0038(17) C3 0.016(2) 0.016(2) 0.0100(19) -0.0017(17) 0.0010(17) -0.001(2) C4 0.017(2) 0.009(2) 0.014(2) -0.0018(16) 0.0029(19) 0.0023(19) C5 0.015(2) 0.021(2) 0.0073(19) -0.0013(17) 0.0018(17) 0.004(2) C6 0.017(2) 0.011(2) 0.023(2) -0.0010(19) 0.0011(19) 0.002(2) C7 0.014(2) 0.014(2) 0.022(2) 0.0065(19) -0.0039(18) -0.0013(19) C8 0.009(2) 0.015(2) 0.0094(19) 0.0003(17) -0.0006(16) 0.0068(18) C9 0.022(3) 0.009(2) 0.039(3) -0.005(2) 0.005(2) -0.004(2) C10 0.012(2) 0.015(3) 0.052(3) -0.003(2) 0.007(2) -0.001(2) C11 0.017(2) 0.013(2) 0.0079(18) 0.0046(19) 0.0045(15) -0.003(2) C12 0.018(2) 0.008(2) 0.0044(18) -0.0001(14) -0.0037(15) -0.0007(17) C13 0.0131(19) 0.008(2) 0.0140(19) 0.0014(18) -0.0036(16) -0.002(2) C14 0.0086(19) 0.009(2) 0.0115(19) 0.0030(16) 0.0030(15) 0.0047(17) C15 0.026(2) 0.013(2) 0.0107(19) 0.0025(17) 0.004(2) 0.008(2) C16 0.029(3) 0.014(3) 0.069(4) 0.008(3) -0.018(3) -0.005(2) C17 0.027(3) 0.016(3) 0.059(4) 0.007(2) -0.015(3) 0.003(2) C18 0.018(2) 0.012(2) 0.008(2) 0.0023(16) -0.0008(16) -0.0010(19) C19 0.021(2) 0.008(2) 0.037(3) 0.008(2) 0.002(2) -0.0039(19) C20 0.016(2) 0.013(2) 0.031(3) 0.006(2) -0.0035(19) -0.0038(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2 2.263(3) 1_455 ? Cd1 O9 2.306(3) . ? Cd1 N2 2.340(4) . ? Cd1 O5 2.346(3) . ? Cd1 O7 2.364(3) . ? Cd1 N3 2.389(4) . ? Cd2 O8 2.213(3) 2_545 ? Cd2 O3 2.310(3) . ? Cd2 N4 2.328(4) . ? Cd2 O1 2.362(3) 4_435 ? Cd2 N1 2.377(3) 4_435 ? Cd2 O4 2.476(3) . ? Cd2 C4 2.750(5) . ? O1 C1 1.254(5) . ? O1 Cd2 2.362(3) 4_535 ? O2 C1 1.271(6) . ? O2 Cd1 2.263(3) 1_655 ? O3 C4 1.273(5) . ? O4 C4 1.256(6) . ? O5 C11 1.270(6) . ? O6 C11 1.253(6) . ? O7 C14 1.253(5) . ? O8 C14 1.275(5) . ? O8 Cd2 2.213(3) 2_544 ? N1 C2 1.483(5) . ? N1 C5 1.494(6) . ? N1 Cd2 2.377(3) 4_535 ? N2 C6 1.340(6) . ? N2 C10 1.346(6) . ? N3 C15 1.480(5) . ? N3 C12 1.480(6) . ? N4 C20 1.331(6) . ? N4 C16 1.340(7) . ? C1 C2 1.535(6) . ? C2 C3 1.543(6) . ? C3 C4 1.495(7) . ? C5 C8 1.510(6) . ? C6 C7 1.387(7) . ? C7 C8 1.394(7) . ? C8 C9 1.377(7) . ? C9 C10 1.370(7) . ? C11 C12 1.534(6) . ? C12 C13 1.534(6) . ? C13 C14 1.506(5) . ? C15 C18 1.503(6) . ? C16 C17 1.372(7) . ? C17 C18 1.372(7) . ? C18 C19 1.394(7) . ? C19 C20 1.390(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cd1 O9 89.35(11) 1_455 . ? O2 Cd1 N2 115.83(13) 1_455 . ? O9 Cd1 N2 104.86(13) . . ? O2 Cd1 O5 81.59(12) 1_455 . ? O9 Cd1 O5 85.11(11) . . ? N2 Cd1 O5 159.49(12) . . ? O2 Cd1 O7 159.11(12) 1_455 . ? O9 Cd1 O7 75.67(11) . . ? N2 Cd1 O7 82.56(12) . . ? O5 Cd1 O7 82.68(11) . . ? O2 Cd1 N3 105.40(12) 1_455 . ? O9 Cd1 N3 148.79(12) . . ? N2 Cd1 N3 93.39(13) . . ? O5 Cd1 N3 70.49(12) . . ? O7 Cd1 N3 82.02(12) . . ? O8 Cd2 O3 100.01(11) 2_545 . ? O8 Cd2 N4 111.22(13) 2_545 . ? O3 Cd2 N4 95.07(12) . . ? O8 Cd2 O1 82.35(12) 2_545 4_435 ? O3 Cd2 O1 99.26(11) . 4_435 ? N4 Cd2 O1 158.26(12) . 4_435 ? O8 Cd2 N1 92.69(12) 2_545 4_435 ? O3 Cd2 N1 162.48(11) . 4_435 ? N4 Cd2 N1 91.47(12) . 4_435 ? O1 Cd2 N1 70.36(11) 4_435 4_435 ? O8 Cd2 O4 150.36(12) 2_545 . ? O3 Cd2 O4 54.56(10) . . ? N4 Cd2 O4 88.18(13) . . ? O1 Cd2 O4 86.92(12) 4_435 . ? N1 Cd2 O4 109.58(12) 4_435 . ? O8 Cd2 C4 126.41(13) 2_545 . ? O3 Cd2 C4 27.43(12) . . ? N4 Cd2 C4 90.76(13) . . ? O1 Cd2 C4 94.45(12) 4_435 . ? N1 Cd2 C4 136.55(13) 4_435 . ? O4 Cd2 C4 27.17(12) . . ? C1 O1 Cd2 116.8(3) . 4_535 ? C1 O2 Cd1 117.3(3) . 1_655 ? C4 O3 Cd2 95.9(3) . . ? C4 O4 Cd2 88.6(2) . . ? C11 O5 Cd1 113.4(3) . . ? C14 O7 Cd1 130.8(3) . . ? C14 O8 Cd2 113.2(3) . 2_544 ? C2 N1 C5 112.6(3) . . ? C2 N1 Cd2 107.1(2) . 4_535 ? C5 N1 Cd2 107.5(2) . 4_535 ? C6 N2 C10 116.8(4) . . ? C6 N2 Cd1 117.4(3) . . ? C10 N2 Cd1 125.8(3) . . ? C15 N3 C12 111.8(3) . . ? C15 N3 Cd1 114.5(3) . . ? C12 N3 Cd1 103.7(2) . . ? C20 N4 C16 116.4(4) . . ? C20 N4 Cd2 118.5(3) . . ? C16 N4 Cd2 124.8(3) . . ? O1 C1 O2 123.5(4) . . ? O1 C1 C2 118.8(4) . . ? O2 C1 C2 117.7(4) . . ? N1 C2 C1 109.2(3) . . ? N1 C2 C3 109.7(4) . . ? C1 C2 C3 108.7(3) . . ? C4 C3 C2 114.6(4) . . ? O4 C4 O3 120.7(4) . . ? O4 C4 C3 121.0(4) . . ? O3 C4 C3 118.2(4) . . ? O4 C4 Cd2 64.2(2) . . ? O3 C4 Cd2 56.7(2) . . ? C3 C4 Cd2 173.4(3) . . ? N1 C5 C8 112.9(3) . . ? N2 C6 C7 123.6(4) . . ? C6 C7 C8 119.0(4) . . ? C9 C8 C7 116.9(4) . . ? C9 C8 C5 121.3(4) . . ? C7 C8 C5 121.7(4) . . ? C10 C9 C8 121.0(5) . . ? N2 C10 C9 122.7(5) . . ? O6 C11 O5 125.9(4) . . ? O6 C11 C12 116.2(4) . . ? O5 C11 C12 117.9(4) . . ? N3 C12 C13 111.8(4) . . ? N3 C12 C11 112.7(4) . . ? C13 C12 C11 109.6(3) . . ? C14 C13 C12 116.7(3) . . ? O7 C14 O8 123.0(4) . . ? O7 C14 C13 120.9(4) . . ? O8 C14 C13 115.9(4) . . ? N3 C15 C18 110.9(4) . . ? N4 C16 C17 123.5(5) . . ? C16 C17 C18 120.3(5) . . ? C17 C18 C19 117.1(4) . . ? C17 C18 C15 122.7(4) . . ? C19 C18 C15 120.2(4) . . ? C20 C19 C18 118.7(4) . . ? N4 C20 C19 123.8(4) . . ? 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 O9 H9A OW1 0.77 1.87 2.636(4) 168.8 . O9 H9B O3 0.80 2.07 2.874(4) 175.8 2_544 OW1 HW1A OW2 0.97 1.78 2.720(5) 162.7 2_444 OW1 HW1B O8 1.01 1.82 2.776(5) 157.8 3_544 OW2 HW2A O6 0.95 1.79 2.731(5) 168.8 4_445 OW2 HW2B O2 0.84 2.27 2.850(5) 125.9 1_455 OW3 HW3A O9 1.03 2.08 2.987(5) 146.3 . OW3 HW3B O5 1.00 1.88 2.860(5) 163.9 . N1 H1A O4 0.94 2.07 2.835(5) 137.1 . N3 H3A O6 0.92 2.25 3.075(5) 149.1 4_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.440 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.093 # Attachment '- AspCo.cif' data_AspCo _database_code_depnum_ccdc_archive 'CCDC 793342' #TrackingRef '- AspCo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Co N2 O7' _chemical_formula_weight 335.18 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 9.3702(6) _cell_length_b 9.3702(6) _cell_length_c 14.7404(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1294.22(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6463 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.60 _exptl_crystal_description Bloc _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.681 _exptl_absorpt_correction_T_max 0.827 _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 6463 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.60 _reflns_number_total 2122 _reflns_number_gt 2052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELX-97' _computing_structure_refinement 'Siemens SHELX-97' _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^)+(0.0159P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(13) _refine_ls_number_reflns 2122 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0554 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.60008(3) 0.07362(4) 0.00625(2) 0.01838(10) Uani 1 1 d . . . O1 O 0.5434(2) -0.0397(2) -0.10950(12) 0.0259(4) Uani 1 1 d . . . O2 O 0.4413(3) 0.0246(3) -0.23953(16) 0.0421(5) Uani 1 1 d . . . O3 O 0.6322(2) 0.2591(2) -0.07186(14) 0.0287(4) Uani 1 1 d . . . O4 O 0.5855(3) 0.4540(3) -0.15149(18) 0.0489(7) Uani 1 1 d . . . O5 O 0.5785(2) -0.1207(2) 0.08544(14) 0.0316(5) Uani 1 1 d . . . H5A H 0.6107 -0.2135 0.0833 0.038 Uiso 1 1 d . . . H5B H 0.5575 -0.0974 0.1434 0.038 Uiso 1 1 d . . . O6 O 0.6033(2) 0.1815(2) 0.12863(12) 0.0298(5) Uani 1 1 d . . . H6A H 0.5238 0.2228 0.1495 0.036 Uiso 1 1 d . . . H6B H 0.5895 0.1178 0.1684 0.036 Uiso 1 1 d . . . OW O 0.6806(3) -0.3954(4) 0.0925(3) 0.0816(11) Uani 1 1 d . . . HWA H 0.7183 -0.4541 0.1345 0.098 Uiso 1 1 d . . . HWB H 0.6001 -0.4397 0.0658 0.098 Uiso 1 1 d . . . N1 N 0.3733(2) 0.1188(2) -0.00728(15) 0.0201(5) Uani 1 1 d . . . H1A H 0.3585 0.1885 0.0235 0.024 Uiso 1 1 d . . . N2 N -0.1760(2) 0.0500(2) 0.00368(15) 0.0192(4) Uani 1 1 d . . . C1 C 0.4562(3) 0.0333(3) -0.15590(18) 0.0240(6) Uani 1 1 d . . . C2 C 0.3592(3) 0.1413(3) -0.10556(17) 0.0209(5) Uani 1 1 d . . . H2A H 0.2600 0.1219 -0.1227 0.025 Uiso 1 1 calc R . . C3 C 0.3945(3) 0.2933(3) -0.1327(2) 0.0276(6) Uani 1 1 d . . . H3A H 0.3322 0.3573 -0.0994 0.033 Uiso 1 1 calc R . . H3B H 0.3734 0.3048 -0.1967 0.033 Uiso 1 1 calc R . . C4 C 0.5480(3) 0.3387(3) -0.1163(2) 0.0265(6) Uani 1 1 d . . . C5 C 0.2794(3) 0.0041(3) 0.02680(17) 0.0232(6) Uani 1 1 d . . . H5C H 0.2963 -0.0068 0.0913 0.028 Uiso 1 1 calc R . . H5D H 0.3070 -0.0845 -0.0023 0.028 Uiso 1 1 calc R . . C6 C -0.1101(3) -0.0742(3) -0.01387(17) 0.0223(6) Uani 1 1 d . . . H6C H -0.1656 -0.1534 -0.0281 0.027 Uiso 1 1 calc R . . C7 C 0.0358(3) -0.0893(3) -0.01167(17) 0.0230(6) Uani 1 1 d . . . H7A H 0.0772 -0.1766 -0.0262 0.028 Uiso 1 1 calc R . . C8 C 0.1212(3) 0.0256(3) 0.01225(18) 0.0194(5) Uani 1 1 d . . . C9 C 0.0538(3) 0.1552(3) 0.02735(17) 0.0244(6) Uani 1 1 d . . . H9A H 0.1072 0.2360 0.0414 0.029 Uiso 1 1 calc R . . C10 C -0.0935(3) 0.1636(3) 0.02133(17) 0.0230(6) Uani 1 1 d . . . H10A H -0.1370 0.2518 0.0299 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01344(16) 0.02330(18) 0.01839(15) -0.00043(14) -0.00074(13) 0.00051(14) O1 0.0250(11) 0.0294(11) 0.0234(10) -0.0061(8) -0.0030(8) 0.0030(8) O2 0.0496(13) 0.0568(14) 0.0199(9) -0.0049(11) -0.0046(10) 0.0098(12) O3 0.0196(10) 0.0275(11) 0.0392(11) 0.0078(9) -0.0028(9) -0.0028(9) O4 0.0356(14) 0.0381(14) 0.0729(18) 0.0303(12) -0.0115(11) -0.0133(11) O5 0.0368(12) 0.0283(12) 0.0297(11) 0.0055(9) 0.0002(9) 0.0012(9) O6 0.0309(12) 0.0339(12) 0.0246(10) -0.0040(9) 0.0000(8) 0.0074(9) OW 0.0412(17) 0.0451(18) 0.158(4) 0.0184(19) 0.0073(18) -0.0006(14) N1 0.0173(11) 0.0236(12) 0.0194(11) -0.0030(9) 0.0014(9) 0.0002(9) N2 0.0160(10) 0.0231(11) 0.0186(9) 0.0004(9) -0.0029(11) -0.0021(8) C1 0.0236(15) 0.0242(14) 0.0241(14) -0.0023(11) -0.0009(11) -0.0029(12) C2 0.0151(13) 0.0255(14) 0.0220(13) 0.0017(11) -0.0029(10) -0.0031(11) C3 0.0242(15) 0.0253(15) 0.0334(15) 0.0074(12) -0.0034(12) 0.0031(12) C4 0.0250(15) 0.0255(15) 0.0290(14) 0.0044(11) 0.0029(12) 0.0000(12) C5 0.0166(13) 0.0307(15) 0.0224(14) 0.0078(10) 0.0009(10) 0.0008(11) C6 0.0198(13) 0.0227(14) 0.0245(16) -0.0006(11) -0.0033(10) -0.0031(11) C7 0.0242(14) 0.0204(14) 0.0244(15) -0.0005(10) 0.0001(11) 0.0054(11) C8 0.0173(12) 0.0257(14) 0.0153(11) 0.0042(11) 0.0010(11) 0.0007(10) C9 0.0190(13) 0.0243(15) 0.0299(15) -0.0028(11) 0.0016(10) -0.0038(11) C10 0.0217(13) 0.0236(14) 0.0237(14) -0.0033(11) 0.0010(10) 0.0035(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O6 2.0681(19) . ? Co1 O1 2.0788(19) . ? Co1 O3 2.106(2) . ? Co1 N2 2.1103(19) 1_655 ? Co1 O5 2.172(2) . ? Co1 N1 2.176(2) . ? O1 C1 1.266(3) . ? O2 C1 1.243(3) . ? O3 C4 1.269(3) . ? O4 C4 1.248(4) . ? N1 C2 1.470(3) . ? N1 C5 1.477(3) . ? N2 C10 1.341(3) . ? N2 C6 1.342(4) . ? N2 Co1 2.1103(19) 1_455 ? C1 C2 1.549(4) . ? C2 C3 1.516(4) . ? C3 C4 1.519(4) . ? C5 C8 1.511(4) . ? C6 C7 1.375(4) . ? C7 C8 1.387(4) . ? C8 C9 1.387(4) . ? C9 C10 1.385(4) . ? 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 Co1 O1 165.78(8) . . ? O6 Co1 O3 94.10(9) . . ? O1 Co1 O3 90.53(8) . . ? O6 Co1 N2 93.01(8) . 1_655 ? O1 Co1 N2 100.70(8) . 1_655 ? O3 Co1 N2 86.25(8) . 1_655 ? O6 Co1 O5 86.70(8) . . ? O1 Co1 O5 89.37(8) . . ? O3 Co1 O5 177.00(8) . . ? N2 Co1 O5 90.82(8) 1_655 . ? O6 Co1 N1 89.94(8) . . ? O1 Co1 N1 76.97(8) . . ? O3 Co1 N1 85.93(8) . . ? N2 Co1 N1 171.82(9) 1_655 . ? O5 Co1 N1 96.96(8) . . ? C1 O1 Co1 109.41(18) . . ? C4 O3 Co1 132.78(19) . . ? C2 N1 C5 112.7(2) . . ? C2 N1 Co1 101.87(15) . . ? C5 N1 Co1 114.16(17) . . ? C10 N2 C6 117.4(2) . . ? C10 N2 Co1 119.11(18) . 1_455 ? C6 N2 Co1 123.47(17) . 1_455 ? O2 C1 O1 124.9(3) . . ? O2 C1 C2 116.9(2) . . ? O1 C1 C2 118.2(2) . . ? N1 C2 C3 112.0(2) . . ? N1 C2 C1 109.0(2) . . ? C3 C2 C1 111.1(2) . . ? C2 C3 C4 115.3(2) . . ? O4 C4 O3 123.3(3) . . ? O4 C4 C3 116.3(2) . . ? O3 C4 C3 120.4(3) . . ? N1 C5 C8 116.1(2) . . ? N2 C6 C7 122.8(3) . . ? C6 C7 C8 120.0(3) . . ? C9 C8 C7 117.3(2) . . ? C9 C8 C5 122.7(2) . . ? C7 C8 C5 119.9(2) . . ? C8 C9 C10 119.5(2) . . ? N2 C10 C9 122.8(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 O5 H5A OW 0.92 1.83 2.748(4) 173.5 . O5 H5B O2 0.90 1.86 2.739(3) 165.2 2_655 O6 H6A O4 0.89 2.05 2.631(3) 121.2 4_565 O6 H6B O2 0.85 1.93 2.772(3) 179.0 2_655 OW HWA O1 0.90 2.42 3.048(4) 127.2 4_655 OW HWB O4 0.95 1.99 2.773(4) 138.3 4 N1 H1A O4 0.81 2.55 3.269(3) 148.8 4_565 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.60 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.266 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.064 # Attachment '- AspNi.cif' data_AspNi _database_code_depnum_ccdc_archive 'CCDC 793343' #TrackingRef '- AspNi.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 N2 Ni O6' _chemical_formula_weight 316.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.0278(3) _cell_length_b 12.0022(6) _cell_length_c 9.2687(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.549(4) _cell_angle_gamma 90.00 _cell_volume 664.74(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2565 _cell_measurement_theta_min 4.81 _cell_measurement_theta_max 61.12 _exptl_crystal_description bloc _exptl_crystal_colour green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 2.358 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.772 _exptl_absorpt_process_details CrysAlisPro _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\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 2565 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.81 _diffrn_reflns_theta_max 61.12 _reflns_number_total 1583 _reflns_number_gt 1471 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0710P)^2^+0.2228P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(5) _refine_ls_number_reflns 1583 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 Ni1 Ni 0.96772(12) 0.10334(6) 0.52375(7) 0.0220(2) Uani 1 1 d . . . O1 O 0.6452(6) 0.0470(3) 0.4705(4) 0.0279(8) Uani 1 1 d . . . O2 O 0.4270(6) -0.0297(4) 0.2826(5) 0.0419(10) Uani 1 1 d . . . O3 O 1.0860(6) -0.0560(3) 0.5515(4) 0.0290(8) Uani 1 1 d . . . O4 O 1.1393(6) -0.2319(3) 0.5060(4) 0.0255(8) Uani 1 1 d . . . O5 O 1.2970(5) 0.1592(3) 0.5495(4) 0.0300(8) Uani 1 1 d . . . H5C H 1.3189 0.2235 0.5180 0.036 Uiso 1 1 d . . . H5D H 1.4257 0.1080 0.5368 0.036 Uiso 1 1 d . . . OW O 0.5869(8) 0.8259(4) 0.6337(6) 0.0637(14) Uani 1 1 d . . . HWA H 0.5992 0.9103 0.6187 0.076 Uiso 1 1 d . . . HWB H 0.4241 0.8175 0.5977 0.076 Uiso 1 1 d . . . N1 N 0.9771(6) 0.0766(3) 0.3015(4) 0.0229(11) Uani 1 1 d . . . H11A H 1.1168 0.0522 0.2902 0.028 Uiso 1 1 calc R . . N2 N 0.9411(6) 0.1114(4) -0.2548(4) 0.0258(8) Uani 1 1 d . . . C1 C 0.6089(9) 0.0018(5) 0.3438(5) 0.0274(11) Uani 1 1 d . . . C2 C 0.8197(9) -0.0179(4) 0.2687(5) 0.0237(10) Uani 1 1 d . . . H2A H 0.7741 -0.0202 0.1633 0.028 Uiso 1 1 calc R . . C3 C 0.9315(8) -0.1284(4) 0.3152(5) 0.0245(11) Uani 1 1 d . . . H3A H 1.0356 -0.1459 0.2471 0.029 Uiso 1 1 calc R . . H3B H 0.8167 -0.1855 0.3044 0.029 Uiso 1 1 calc R . . C4 C 1.0582(7) -0.1384(4) 0.4690(4) 0.0199(11) Uani 1 1 d . . . C5 C 0.9236(9) 0.1716(4) 0.2024(5) 0.0299(12) Uani 1 1 d . . . H5A H 1.0294 0.2311 0.2308 0.036 Uiso 1 1 calc R . . H5B H 0.7758 0.1989 0.2147 0.036 Uiso 1 1 calc R . . C6 C 0.7679(9) 0.1623(5) -0.2064(5) 0.0312(12) Uani 1 1 d . . . H6A H 0.6494 0.1860 -0.2739 0.037 Uiso 1 1 calc R . . C7 C 0.7572(9) 0.1811(5) -0.0615(6) 0.0339(12) Uani 1 1 d . . . H7A H 0.6339 0.2176 -0.0331 0.041 Uiso 1 1 calc R . . C8 C 0.9280(9) 0.1464(5) 0.0421(5) 0.0287(11) Uani 1 1 d . . . C9 C 1.1049(9) 0.0915(6) -0.0082(5) 0.0411(14) Uani 1 1 d . . . H9A H 1.2240 0.0658 0.0573 0.049 Uiso 1 1 calc R . . C10 C 1.1044(10) 0.0753(5) -0.1538(6) 0.0376(15) Uani 1 1 d . . . H10A H 1.2239 0.0370 -0.1846 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0271(4) 0.0245(4) 0.0143(4) 0.0000(3) 0.0024(3) 0.0010(4) O1 0.0263(18) 0.034(2) 0.0244(18) -0.0082(15) 0.0057(14) -0.0021(16) O2 0.025(2) 0.060(3) 0.040(2) -0.0153(19) 0.0017(17) -0.0048(18) O3 0.040(2) 0.0228(19) 0.0224(16) -0.0006(16) -0.0013(15) 0.0043(15) O4 0.0298(18) 0.0206(18) 0.0245(18) 0.0010(13) -0.0022(15) -0.0002(14) O5 0.0241(18) 0.0309(19) 0.0345(18) -0.0041(16) 0.0017(14) 0.0012(15) OW 0.052(3) 0.066(4) 0.070(3) -0.007(3) -0.003(2) 0.013(2) N1 0.0200(18) 0.034(3) 0.0147(18) 0.0020(17) 0.0007(14) -0.0003(17) N2 0.0301(19) 0.029(2) 0.0184(17) 0.000(2) 0.0036(15) -0.003(2) C1 0.028(3) 0.029(3) 0.024(3) 0.003(2) -0.001(2) -0.001(2) C2 0.026(3) 0.029(3) 0.015(2) 0.0002(19) -0.0016(18) 0.000(2) C3 0.025(3) 0.030(3) 0.019(2) -0.004(2) 0.0028(19) -0.004(2) C4 0.024(3) 0.019(3) 0.017(3) 0.0016(19) 0.0030(18) -0.003(2) C5 0.041(3) 0.027(3) 0.024(3) 0.003(2) 0.008(2) 0.001(2) C6 0.029(3) 0.043(3) 0.020(2) -0.001(2) -0.003(2) 0.001(2) C7 0.033(3) 0.044(3) 0.026(3) 0.005(2) 0.008(2) 0.003(2) C8 0.039(3) 0.029(3) 0.018(2) 0.0035(19) 0.003(2) -0.005(2) C9 0.039(3) 0.061(4) 0.022(2) 0.008(3) 0.001(2) 0.016(3) C10 0.042(3) 0.047(4) 0.025(3) 0.003(2) 0.005(2) 0.013(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 Ni1 O3 2.045(4) . ? Ni1 O1 2.056(3) . ? Ni1 O5 2.079(3) . ? Ni1 N2 2.082(3) 1_556 ? Ni1 O4 2.087(4) 2_756 ? Ni1 N1 2.093(4) . ? O1 C1 1.286(6) . ? O2 C1 1.226(6) . ? O3 C4 1.248(6) . ? O4 C4 1.253(6) . ? O4 Ni1 2.087(4) 2_746 ? N1 C5 1.474(6) . ? N1 C2 1.484(6) . ? N2 C6 1.337(7) . ? N2 C10 1.339(7) . ? N2 Ni1 2.082(3) 1_554 ? C1 C2 1.546(7) . ? C2 C3 1.524(7) . ? C3 C4 1.531(6) . ? C5 C8 1.520(7) . ? C6 C7 1.371(8) . ? C7 C8 1.377(8) . ? C8 C9 1.385(8) . ? C9 C10 1.363(8) . ? 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 Ni1 O1 91.47(16) . . ? O3 Ni1 O5 88.56(15) . . ? O1 Ni1 O5 172.74(14) . . ? O3 Ni1 N2 89.44(17) . 1_556 ? O1 Ni1 N2 93.37(15) . 1_556 ? O5 Ni1 N2 93.90(15) . 1_556 ? O3 Ni1 O4 177.54(15) . 2_756 ? O1 Ni1 O4 90.81(14) . 2_756 ? O5 Ni1 O4 89.06(14) . 2_756 ? N2 Ni1 O4 91.34(17) 1_556 2_756 ? O3 Ni1 N1 85.78(14) . . ? O1 Ni1 N1 81.98(14) . . ? O5 Ni1 N1 90.78(14) . . ? N2 Ni1 N1 173.22(19) 1_556 . ? O4 Ni1 N1 93.64(14) 2_756 . ? C1 O1 Ni1 113.6(3) . . ? C4 O3 Ni1 130.3(3) . . ? C4 O4 Ni1 135.2(3) . 2_746 ? C5 N1 C2 112.5(4) . . ? C5 N1 Ni1 117.6(3) . . ? C2 N1 Ni1 102.7(3) . . ? C6 N2 C10 116.6(4) . . ? C6 N2 Ni1 121.1(3) . 1_554 ? C10 N2 Ni1 122.0(3) . 1_554 ? O2 C1 O1 126.0(5) . . ? O2 C1 C2 118.8(5) . . ? O1 C1 C2 115.1(4) . . ? N1 C2 C3 111.1(4) . . ? N1 C2 C1 109.4(4) . . ? C3 C2 C1 111.4(4) . . ? C2 C3 C4 118.7(4) . . ? O3 C4 O4 121.7(4) . . ? O3 C4 C3 121.3(4) . . ? O4 C4 C3 117.0(4) . . ? N1 C5 C8 115.1(4) . . ? N2 C6 C7 122.9(5) . . ? C6 C7 C8 120.4(5) . . ? C7 C8 C9 116.6(5) . . ? C7 C8 C5 120.9(5) . . ? C9 C8 C5 122.5(5) . . ? C10 C9 C8 120.0(5) . . ? N2 C10 C9 123.5(5) . . ? 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 O5 H5C OW 0.84 2.00 2.773(6) 151.3 2_746 O5 H5D O1 1.01 1.70 2.675(4) 162.5 1_655 OW HWA O1 1.03 2.18 3.097(7) 147.7 1_565 OW HWB O4 1.00 1.91 2.885(6) 165.3 1_465 OW HWB O3 1.00 2.53 3.332(6) 136.8 1_465 N1 H11A O2 0.91 2.12 3.023(5) 170.1 1_655 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 61.12 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.508 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.076 # Attachment '- AspZn.cif' data_AspZn _database_code_depnum_ccdc_archive 'CCDC 793344' #TrackingRef '- AspZn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N2 O7 Zn' _chemical_formula_weight 341.62 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 tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 9.3479(2) _cell_length_b 9.3479(2) _cell_length_c 14.7797(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1291.50(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7106 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 25.05 _exptl_crystal_description Bloc _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 1.936 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_T_max 0.925 _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 7106 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2083 _reflns_number_gt 1793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELX-97' _computing_structure_refinement 'Siemens SHELX-97' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.003(11) _refine_ls_number_reflns 2083 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0454 _refine_ls_wR_factor_gt 0.0441 _refine_ls_goodness_of_fit_ref 0.789 _refine_ls_restrained_S_all 0.789 _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 0.60212(4) 0.06857(4) 0.00675(3) 0.02178(11) Uani 1 1 d . . . O1 O 0.5449(3) -0.0440(3) -0.11137(16) 0.0274(6) Uani 1 1 d . . . O2 O 0.4452(3) 0.0252(3) -0.2410(2) 0.0414(7) Uani 1 1 d . . . O3 O 0.6338(3) 0.2581(3) -0.07479(16) 0.0319(7) Uani 1 1 d . . . O4 O 0.5887(3) 0.4520(3) -0.15454(19) 0.0498(9) Uani 1 1 d . . . O5 O 0.5786(3) -0.1233(3) 0.08630(18) 0.0336(7) Uani 1 1 d . . . H5A H 0.6107 -0.2135 0.0833 0.040 Uiso 1 1 d . . . H5B H 0.5575 -0.0974 0.1434 0.040 Uiso 1 1 d . . . O6 O 0.6059(3) 0.1821(3) 0.12793(15) 0.0303(7) Uani 1 1 d . . . H6A H 0.5238 0.2228 0.1495 0.036 Uiso 1 1 d . . . H6B H 0.5895 0.1178 0.1684 0.036 Uiso 1 1 d . . . OW O 0.6772(3) -0.3975(3) 0.0913(3) 0.0810(12) Uani 1 1 d . . . HWA H 0.7183 -0.4541 0.1345 0.097 Uiso 1 1 d . . . HWB H 0.6001 -0.4397 0.0658 0.097 Uiso 1 1 d . . . N1 N 0.3757(3) 0.1154(3) -0.00880(18) 0.0225(7) Uani 1 1 d . . . H1A H 0.3585 0.1885 0.0235 0.027 Uiso 1 1 d . . . N2 N -0.1760(3) 0.0491(3) 0.0020(2) 0.0212(7) Uani 1 1 d . . . C1 C 0.4604(4) 0.0314(4) -0.1575(3) 0.0248(9) Uani 1 1 d . . . C2 C 0.3616(4) 0.1386(4) -0.1062(2) 0.0230(9) Uani 1 1 d . . . H2A H 0.2623 0.1190 -0.1235 0.028 Uiso 1 1 calc R . . C3 C 0.3970(4) 0.2927(4) -0.1332(2) 0.0278(9) Uani 1 1 d . . . H3A H 0.3742 0.3050 -0.1967 0.033 Uiso 1 1 calc R . . H3B H 0.3355 0.3566 -0.0991 0.033 Uiso 1 1 calc R . . C4 C 0.5504(4) 0.3377(4) -0.1184(3) 0.0273(9) Uani 1 1 d . . . C5 C 0.2805(3) 0.0031(4) 0.0253(2) 0.0241(9) Uani 1 1 d . . . H5C H 0.2969 -0.0067 0.0898 0.029 Uiso 1 1 calc R . . H5D H 0.3081 -0.0865 -0.0028 0.029 Uiso 1 1 calc R . . C6 C -0.1099(4) -0.0755(4) -0.0152(2) 0.0232(9) Uani 1 1 d . . . H6C H -0.1654 -0.1551 -0.0292 0.028 Uiso 1 1 calc R . . C7 C 0.0369(4) -0.0907(4) -0.0130(2) 0.0236(9) Uani 1 1 d . . . H7A H 0.0786 -0.1781 -0.0274 0.028 Uiso 1 1 calc R . . C8 C 0.1212(3) 0.0238(4) 0.0105(3) 0.0197(8) Uani 1 1 d . . . C9 C 0.0541(4) 0.1536(4) 0.0251(2) 0.0247(9) Uani 1 1 d . . . H9A H 0.1079 0.2345 0.0386 0.030 Uiso 1 1 calc R . . C10 C -0.0936(3) 0.1625(4) 0.0197(2) 0.0211(8) Uani 1 1 d . . . H10A H -0.1370 0.2508 0.0286 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0165(2) 0.0275(2) 0.0213(2) -0.0003(2) -0.0012(2) 0.0007(2) O1 0.0249(16) 0.0302(16) 0.0271(14) -0.0068(12) -0.0019(12) 0.0032(12) O2 0.0518(18) 0.0561(18) 0.0164(12) -0.0018(18) -0.0033(16) 0.0122(15) O3 0.0208(15) 0.0299(16) 0.0451(17) 0.0082(14) -0.0079(14) -0.0028(13) O4 0.0404(19) 0.0395(18) 0.070(2) 0.0297(16) -0.0100(16) -0.0096(15) O5 0.0407(17) 0.0282(17) 0.0319(16) 0.0056(14) 0.0033(14) 0.0048(13) O6 0.0286(16) 0.0372(18) 0.0252(15) -0.0039(13) -0.0002(13) 0.0079(13) OW 0.041(2) 0.043(2) 0.159(4) 0.012(2) 0.005(2) 0.0053(18) N1 0.0200(16) 0.0288(18) 0.0187(17) -0.0041(15) 0.0034(14) -0.0005(13) N2 0.0180(15) 0.0282(17) 0.0174(15) 0.0012(17) -0.0019(17) -0.0020(13) C1 0.023(2) 0.022(2) 0.030(2) 0.0010(18) -0.0032(18) -0.0022(18) C2 0.015(2) 0.028(2) 0.025(2) 0.0010(18) -0.0001(17) 0.0002(17) C3 0.017(2) 0.029(2) 0.037(2) 0.0056(19) -0.0033(18) 0.0025(17) C4 0.026(2) 0.029(2) 0.027(2) 0.0011(19) 0.0058(19) -0.0018(19) C5 0.024(2) 0.024(2) 0.024(2) 0.0053(17) 0.0039(17) 0.0023(16) C6 0.025(2) 0.021(2) 0.023(3) 0.0004(17) -0.0014(18) -0.0056(17) C7 0.027(2) 0.019(2) 0.025(2) 0.0004(17) 0.0005(17) 0.0067(16) C8 0.0181(18) 0.027(2) 0.0137(17) 0.001(2) 0.0006(19) 0.0006(15) C9 0.0190(19) 0.027(2) 0.028(2) -0.0037(18) 0.0020(18) -0.0082(16) C10 0.0205(18) 0.0190(19) 0.024(2) -0.0050(18) 0.0008(18) 0.0005(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 O6 2.082(2) . ? Zn1 N2 2.084(2) 1_655 ? Zn1 O1 2.107(2) . ? Zn1 O5 2.156(3) . ? Zn1 O3 2.163(3) . ? Zn1 N1 2.174(3) . ? O1 C1 1.259(4) . ? O2 C1 1.243(4) . ? O3 C4 1.256(4) . ? O4 C4 1.248(4) . ? N1 C2 1.462(4) . ? N1 C5 1.465(4) . ? N2 C10 1.336(4) . ? N2 C6 1.343(4) . ? N2 Zn1 2.084(2) 1_455 ? C1 C2 1.559(5) . ? C2 C3 1.531(5) . ? C3 C4 1.510(5) . ? C5 C8 1.517(4) . ? C6 C7 1.380(5) . ? C7 C8 1.373(4) . ? C8 C9 1.383(4) . ? C9 C10 1.386(4) . ? 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 Zn1 N2 93.23(11) . 1_655 ? O6 Zn1 O1 166.27(9) . . ? N2 Zn1 O1 100.45(11) 1_655 . ? O6 Zn1 O5 87.52(10) . . ? N2 Zn1 O5 92.69(10) 1_655 . ? O1 Zn1 O5 90.60(10) . . ? O6 Zn1 O3 93.40(11) . . ? N2 Zn1 O3 85.21(10) 1_655 . ? O1 Zn1 O3 88.98(10) . . ? O5 Zn1 O3 177.75(10) . . ? O6 Zn1 N1 90.28(9) . . ? N2 Zn1 N1 169.61(11) 1_655 . ? O1 Zn1 N1 76.45(10) . . ? O5 Zn1 N1 97.24(10) . . ? O3 Zn1 N1 84.82(10) . . ? C1 O1 Zn1 109.2(2) . . ? C4 O3 Zn1 133.3(2) . . ? C2 N1 C5 113.0(3) . . ? C2 N1 Zn1 102.8(2) . . ? C5 N1 Zn1 114.2(2) . . ? C10 N2 C6 117.4(3) . . ? C10 N2 Zn1 119.9(2) . 1_455 ? C6 N2 Zn1 122.7(2) . 1_455 ? O2 C1 O1 125.7(4) . . ? O2 C1 C2 116.4(3) . . ? O1 C1 C2 117.9(3) . . ? N1 C2 C3 112.1(3) . . ? N1 C2 C1 109.2(3) . . ? C3 C2 C1 110.5(3) . . ? C4 C3 C2 115.4(3) . . ? O4 C4 O3 123.3(4) . . ? O4 C4 C3 116.6(3) . . ? O3 C4 C3 120.0(3) . . ? N1 C5 C8 117.1(3) . . ? N2 C6 C7 122.8(3) . . ? C8 C7 C6 119.8(3) . . ? C7 C8 C9 117.6(3) . . ? C7 C8 C5 120.0(3) . . ? C9 C8 C5 122.3(3) . . ? C8 C9 C10 119.7(3) . . ? N2 C10 C9 122.6(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 O5 H5A OW 0.90 1.83 2.725(4) 173.4 . O5 H5B O2 0.90 1.84 2.722(4) 166.9 2_655 O6 H6A O4 0.91 2.05 2.625(3) 119.8 4_565 O6 H6B O2 0.86 1.92 2.782(4) 179.4 2_655 OW HWA O1 0.91 2.38 3.030(4) 128.1 4_655 OW HWB O4 0.90 2.01 2.762(4) 139.4 4 N1 H1A O4 0.85 2.50 3.246(4) 147.7 4_565 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.215 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.053 # Attachment '- GluCd.cif' data_GluCd _database_code_depnum_ccdc_archive 'CCDC 793345' #TrackingRef '- GluCd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cd N2 O5' _chemical_formula_weight 366.64 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4907(6) _cell_length_b 9.3897(8) _cell_length_c 16.0819(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1282.13(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10123 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 50.04 _exptl_crystal_description Bloc _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.899 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 1.721 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.655 _exptl_absorpt_correction_T_max 0.842 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 12470 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2632 _reflns_number_gt 2158 _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^)+(0.0218P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_number_reflns 2632 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0545 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 -0.04396(4) -0.57780(4) -0.22271(2) 0.02532(9) Uani 1 1 d . . . O1 O 0.7299(4) -0.6100(4) -0.3036(2) 0.0413(10) Uani 1 1 d . . . O2 O 0.7450(4) -0.7406(4) -0.1909(2) 0.0364(9) Uani 1 1 d . . . O3 O 0.0709(4) -0.8038(3) -0.25325(17) 0.0336(10) Uani 1 1 d . . . O4 O 0.2040(4) -0.9123(4) -0.3520(2) 0.0398(8) Uani 1 1 d . . . OW1 O 0.6251(9) -0.5017(7) -0.4628(4) 0.151(3) Uani 1 1 d . . . HW1 H 0.6355 -0.5555 -0.4194 0.181 Uiso 1 1 d . . . HW2 H 0.6922 -0.5056 -0.5008 0.181 Uiso 1 1 d . . . N1 N 0.1345(4) -0.5486(4) -0.3342(2) 0.0231(10) Uani 1 1 d . . . H1A H 0.1881 -0.4660 -0.3255 0.028 Uiso 1 1 calc R . . N2 N 0.3690(5) -0.4509(5) -0.6132(2) 0.0317(10) Uani 1 1 d . . . C1 C 0.6706(6) -0.6969(5) -0.2524(3) 0.0332(14) Uani 1 1 d . . . C2 C 0.5060(5) -0.7484(5) -0.2698(4) 0.0387(13) Uani 1 1 d . . . H2A H 0.4726 -0.8102 -0.2248 0.046 Uiso 1 1 calc R . . H2B H 0.5066 -0.8043 -0.3205 0.046 Uiso 1 1 calc R . . C3 C 0.3883(5) -0.6282(5) -0.2789(4) 0.0333(12) Uani 1 1 d . . . H3A H 0.4420 -0.5454 -0.3012 0.040 Uiso 1 1 calc R . . H3B H 0.3486 -0.6031 -0.2243 0.040 Uiso 1 1 calc R . . C4 C 0.2493(6) -0.6645(5) -0.3352(3) 0.0241(11) Uani 1 1 d . . . H4A H 0.2891 -0.6737 -0.3922 0.029 Uiso 1 1 calc R . . C5 C 0.1689(5) -0.8032(5) -0.3122(3) 0.0254(11) Uani 1 1 d . . . C6 C 0.0472(6) -0.5334(5) -0.4130(2) 0.0318(11) Uani 1 1 d . . . H6A H -0.0293 -0.4573 -0.4073 0.038 Uiso 1 1 calc R . . H6B H -0.0100 -0.6209 -0.4239 0.038 Uiso 1 1 calc R . . C7 C 0.3154(7) -0.3457(6) -0.5656(3) 0.0439(15) Uani 1 1 d . . . H7A H 0.3500 -0.2536 -0.5764 0.053 Uiso 1 1 calc R . . C8 C 0.2114(8) -0.3667(6) -0.5013(3) 0.0459(16) Uani 1 1 d . . . H8A H 0.1803 -0.2907 -0.4681 0.055 Uiso 1 1 calc R . . C9 C 0.1536(6) -0.5012(6) -0.4866(3) 0.0294(13) Uani 1 1 d . . . C10 C 0.2037(6) -0.6089(5) -0.5391(3) 0.0358(13) Uani 1 1 d . . . H10A H 0.1647 -0.7009 -0.5332 0.043 Uiso 1 1 calc R . . C11 C 0.3113(5) -0.5780(7) -0.5998(3) 0.0344(11) Uani 1 1 d . . . H11A H 0.3456 -0.6521 -0.6337 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02086(15) 0.03061(16) 0.02449(14) -0.00078(19) -0.00081(17) 0.00050(19) O1 0.030(2) 0.047(3) 0.046(2) 0.0082(19) -0.0053(16) -0.0085(18) O2 0.032(2) 0.039(2) 0.039(2) 0.0031(17) -0.0058(17) 0.0036(18) O3 0.031(2) 0.0282(19) 0.041(2) 0.0039(14) 0.0052(16) -0.0073(16) O4 0.040(2) 0.0208(18) 0.058(2) -0.010(2) 0.0046(16) -0.002(2) OW1 0.186(7) 0.159(6) 0.108(5) 0.020(4) -0.051(5) 0.067(5) N1 0.019(2) 0.023(3) 0.027(2) -0.0011(18) 0.0002(18) 0.0012(19) N2 0.036(2) 0.026(3) 0.032(2) 0.004(2) 0.005(2) 0.004(2) C1 0.021(3) 0.025(3) 0.053(4) -0.002(3) 0.001(2) 0.004(2) C2 0.023(3) 0.027(2) 0.067(3) 0.005(3) -0.009(3) -0.0033(18) C3 0.023(3) 0.029(3) 0.048(3) -0.007(3) 0.002(3) -0.006(2) C4 0.022(3) 0.021(3) 0.029(3) 0.002(2) 0.003(2) 0.000(2) C5 0.014(2) 0.025(3) 0.037(3) 0.000(2) -0.006(2) -0.001(2) C6 0.025(2) 0.040(3) 0.030(2) 0.007(2) 0.007(3) 0.004(3) C7 0.057(4) 0.030(3) 0.045(3) 0.003(3) 0.011(3) -0.006(3) C8 0.066(4) 0.032(3) 0.040(3) -0.005(3) 0.019(3) 0.006(3) C9 0.027(3) 0.035(3) 0.027(3) 0.004(2) 0.004(2) 0.007(2) C10 0.051(4) 0.019(3) 0.037(3) 0.000(2) 0.002(3) -0.003(2) C11 0.042(3) 0.033(3) 0.029(2) 0.003(3) 0.005(2) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N2 2.320(4) 2_545 ? Cd1 O1 2.338(3) 1_455 ? Cd1 N1 2.364(4) . ? Cd1 O3 2.387(3) . ? Cd1 O4 2.389(3) 3_554 ? Cd1 O2 2.410(4) 1_455 ? Cd1 O3 2.611(3) 3_554 ? Cd1 C1 2.712(5) 1_455 ? O1 C1 1.263(5) . ? O1 Cd1 2.339(3) 1_655 ? O2 C1 1.243(5) . ? O2 Cd1 2.410(4) 1_655 ? O3 C5 1.262(5) . ? O3 Cd1 2.611(3) 3_544 ? O4 C5 1.244(6) . ? O4 Cd1 2.389(3) 3_544 ? N1 C4 1.461(6) . ? N1 C6 1.474(5) . ? N2 C11 1.308(7) . ? N2 C7 1.330(6) . ? N2 Cd1 2.320(4) 2_544 ? C1 C2 1.505(7) . ? C1 Cd1 2.712(5) 1_655 ? C2 C3 1.514(6) . ? C3 C4 1.526(6) . ? C4 C5 1.516(6) . ? C6 C9 1.519(6) . ? C7 C8 1.374(8) . ? C8 C9 1.375(7) . ? C9 C10 1.385(7) . ? C10 C11 1.368(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cd1 O1 164.35(13) 2_545 1_455 ? N2 Cd1 N1 98.76(12) 2_545 . ? O1 Cd1 N1 96.86(12) 1_455 . ? N2 Cd1 O3 89.89(13) 2_545 . ? O1 Cd1 O3 96.09(12) 1_455 . ? N1 Cd1 O3 71.66(12) . . ? N2 Cd1 O4 84.65(13) 2_545 3_554 ? O1 Cd1 O4 84.07(12) 1_455 3_554 ? N1 Cd1 O4 132.12(12) . 3_554 ? O3 Cd1 O4 156.13(11) . 3_554 ? N2 Cd1 O2 112.88(13) 2_545 1_455 ? O1 Cd1 O2 54.94(12) 1_455 1_455 ? N1 Cd1 O2 135.32(12) . 1_455 ? O3 Cd1 O2 77.49(11) . 1_455 ? O4 Cd1 O2 83.28(12) 3_554 1_455 ? N2 Cd1 O3 93.09(13) 2_545 3_554 ? O1 Cd1 O3 88.46(12) 1_455 3_554 ? N1 Cd1 O3 80.18(12) . 3_554 ? O3 Cd1 O3 151.80(3) . 3_554 ? O4 Cd1 O3 51.96(11) 3_554 3_554 ? O2 Cd1 O3 126.24(12) 1_455 3_554 ? N2 Cd1 C1 138.94(15) 2_545 1_455 ? O1 Cd1 C1 27.73(12) 1_455 1_455 ? N1 Cd1 C1 119.15(13) . 1_455 ? O3 Cd1 C1 87.84(13) . 1_455 ? O4 Cd1 C1 81.28(13) 3_554 1_455 ? O2 Cd1 C1 27.29(12) 1_455 1_455 ? O3 Cd1 C1 107.57(13) 3_554 1_455 ? C1 O1 Cd1 92.8(3) . 1_655 ? C1 O2 Cd1 90.0(3) . 1_655 ? C5 O3 Cd1 114.8(3) . . ? C5 O3 Cd1 87.2(3) . 3_544 ? Cd1 O3 Cd1 150.54(15) . 3_544 ? C5 O4 Cd1 98.1(3) . 3_544 ? C4 N1 C6 113.4(3) . . ? C4 N1 Cd1 110.5(3) . . ? C6 N1 Cd1 109.9(3) . . ? C11 N2 C7 117.0(5) . . ? C11 N2 Cd1 118.1(3) . 2_544 ? C7 N2 Cd1 124.7(4) . 2_544 ? O2 C1 O1 121.9(5) . . ? O2 C1 C2 120.9(5) . . ? O1 C1 C2 117.2(4) . . ? O2 C1 Cd1 62.7(3) . 1_655 ? O1 C1 Cd1 59.5(2) . 1_655 ? C2 C1 Cd1 174.4(3) . 1_655 ? C1 C2 C3 113.0(4) . . ? C2 C3 C4 113.7(4) . . ? N1 C4 C5 109.7(4) . . ? N1 C4 C3 110.1(4) . . ? C5 C4 C3 113.3(4) . . ? O4 C5 O3 122.7(4) . . ? O4 C5 C4 118.3(4) . . ? O3 C5 C4 118.9(4) . . ? N1 C6 C9 112.9(4) . . ? N2 C7 C8 123.1(5) . . ? C7 C8 C9 119.4(5) . . ? C8 C9 C10 117.1(4) . . ? C8 C9 C6 122.0(5) . . ? C10 C9 C6 120.8(5) . . ? C11 C10 C9 119.0(5) . . ? N2 C11 C10 124.2(5) . . ? 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 OW1 HW1 O1 0.87 2.09 2.895(6) 154.1 . OW1 HW2 O4 0.84 2.49 3.158(7) 137.3 4_534 N1 H1A O2 0.91 2.21 3.094(5) 164.6 3_654 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.450 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.081 # Attachment '- GluZn.cif' data_GluZn _database_code_depnum_ccdc_archive 'CCDC 793346' #TrackingRef '- GluZn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 N2 O6 Zn' _chemical_formula_weight 337.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.18800(10) _cell_length_b 7.2073(2) _cell_length_c 8.7257(3) _cell_angle_alpha 102.0420(10) _cell_angle_beta 104.1240(10) _cell_angle_gamma 113.8390(10) _cell_volume 323.824(15) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4330 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 25.79 _exptl_crystal_description Bloc _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 1.924 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.714 _exptl_absorpt_correction_T_max 0.944 _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 4330 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.79 _reflns_number_total 2025 _reflns_number_gt 2021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELX-97' _computing_structure_refinement 'Siemens SHELX-97' _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^)+(0.0136P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.031(8) _refine_ls_number_reflns 2025 _refine_ls_number_parameters 181 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0170 _refine_ls_R_factor_gt 0.0169 _refine_ls_wR_factor_ref 0.0431 _refine_ls_wR_factor_gt 0.0431 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _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 -0.4247 -0.1356 -0.3302 0.02063(8) Uani 1 1 d . . . O1 O 0.0582(4) 0.4886(3) 0.3706(2) 0.0410(5) Uani 1 1 d . . . O2 O 0.4759(3) 0.6886(3) 0.4362(2) 0.0298(4) Uani 1 1 d . . . O3 O -0.0276(4) 0.0034(3) -0.2712(2) 0.0238(5) Uani 1 1 d . . . O4 O 0.3253(3) 0.3177(3) -0.1718(2) 0.0277(4) Uani 1 1 d . . . O5 O -0.7941(4) -0.2393(3) -0.3263(2) 0.0283(5) Uani 1 1 d . . . H5A H -0.8821 -0.1550 -0.3213 0.034 Uiso 1 1 d . . . H5B H -0.8563 -0.3299 -0.4346 0.034 Uiso 1 1 d . . . O6 O -0.3751(4) -0.2899(3) -0.1712(3) 0.0531(6) Uani 1 1 d . . . H6C H -0.5058 -0.4075 -0.1675 0.064 Uiso 1 1 d . . . H6D H -0.2348 -0.2334 -0.0831 0.064 Uiso 1 1 d . . . N1 N -0.3189(4) 0.1952(3) -0.2833(2) 0.0172(4) Uani 1 1 d . . . H1A H -0.4368 0.2182 -0.2464 0.026 Uiso 1 1 d . . . N2 N -0.9691(5) -0.1162(4) -0.8903(3) 0.0368(6) Uani 1 1 d . . . C1 C 0.2486(5) 0.5530(4) 0.3330(3) 0.0223(5) Uani 1 1 d . . . C2 C 0.2250(5) 0.4745(4) 0.1514(3) 0.0251(5) Uani 1 1 d . . . H2A H 0.3102 0.3878 0.1426 0.030 Uiso 1 1 calc R . . H2B H 0.3130 0.5992 0.1218 0.030 Uiso 1 1 calc R . . C3 C -0.0480(5) 0.3407(4) 0.0233(3) 0.0223(5) Uani 1 1 d . . . H3A H -0.1478 0.4087 0.0496 0.027 Uiso 1 1 calc R . . H3B H -0.1231 0.1974 0.0307 0.027 Uiso 1 1 calc R . . C4 C -0.0546(4) 0.3215(4) -0.1568(3) 0.0182(5) Uani 1 1 d . . . H4A H 0.0229 0.4669 -0.1628 0.022 Uiso 1 1 calc R . . C5 C 0.0955(5) 0.2083(4) -0.2030(3) 0.0192(5) Uani 1 1 d . . . C6 C -0.3157(5) 0.2632(4) -0.4334(3) 0.0275(6) Uani 1 1 d . . . H6A H -0.1714 0.2645 -0.4593 0.033 Uiso 1 1 calc R . . H6B H -0.2886 0.4103 -0.4034 0.033 Uiso 1 1 calc R . . C7 C -0.9944(6) -0.0817(5) -0.7426(4) 0.0353(6) Uani 1 1 d . . . H7A H -1.1577 -0.1419 -0.7409 0.042 Uiso 1 1 calc R . . C8 C -0.7930(5) 0.0381(4) -0.5906(3) 0.0305(6) Uani 1 1 d . . . H8A H -0.8210 0.0594 -0.4899 0.037 Uiso 1 1 calc R . . C9 C -0.5507(5) 0.1253(4) -0.5906(3) 0.0216(5) Uani 1 1 d . . . C10 C -0.5214(6) 0.0909(4) -0.7448(3) 0.0302(6) Uani 1 1 d . . . H10A H -0.3603 0.1479 -0.7502 0.036 Uiso 1 1 calc R . . C11 C -0.7347(6) -0.0289(5) -0.8900(3) 0.0390(7) Uani 1 1 d . . . H11A H -0.7132 -0.0496 -0.9929 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01802(13) 0.01915(12) 0.01513(11) 0.00164(8) 0.00201(9) 0.00464(10) O1 0.0294(12) 0.0402(11) 0.0241(10) -0.0051(8) 0.0099(9) -0.0021(9) O2 0.0238(10) 0.0333(10) 0.0155(8) -0.0044(7) -0.0004(7) 0.0089(8) O3 0.0182(10) 0.0190(10) 0.0276(12) 0.0003(9) 0.0072(9) 0.0073(8) O4 0.0142(9) 0.0272(9) 0.0334(9) 0.0038(7) 0.0081(7) 0.0062(8) O5 0.0239(11) 0.0268(11) 0.0279(12) 0.0032(9) 0.0088(10) 0.0099(9) O6 0.0263(11) 0.0490(12) 0.0481(12) 0.0336(10) -0.0135(9) -0.0070(10) N1 0.0121(10) 0.0201(9) 0.0155(8) 0.0039(7) 0.0034(8) 0.0063(8) N2 0.0306(15) 0.0312(12) 0.0271(12) 0.0077(10) -0.0055(10) 0.0058(12) C1 0.0234(14) 0.0198(13) 0.0168(11) 0.0019(9) 0.0041(10) 0.0080(11) C2 0.0216(14) 0.0266(12) 0.0165(11) -0.0006(9) 0.0023(10) 0.0088(11) C3 0.0195(13) 0.0252(13) 0.0156(11) 0.0013(9) 0.0033(10) 0.0093(11) C4 0.0135(12) 0.0179(11) 0.0153(10) 0.0020(8) 0.0014(9) 0.0044(10) C5 0.0172(13) 0.0229(12) 0.0134(10) 0.0056(9) 0.0050(9) 0.0068(10) C6 0.0218(14) 0.0311(13) 0.0180(11) 0.0094(10) 0.0011(10) 0.0054(11) C7 0.0189(14) 0.0394(17) 0.0376(15) 0.0139(13) 0.0027(12) 0.0091(13) C8 0.0253(15) 0.0409(15) 0.0227(13) 0.0108(11) 0.0062(11) 0.0152(13) C9 0.0219(13) 0.0193(11) 0.0188(11) 0.0069(9) 0.0020(10) 0.0084(10) C10 0.0255(15) 0.0340(14) 0.0241(12) 0.0103(11) 0.0059(11) 0.0096(12) C11 0.045(2) 0.0448(17) 0.0169(12) 0.0089(11) 0.0038(12) 0.0176(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 O2 1.9539(16) 1_444 ? Zn1 O6 1.9922(19) . ? Zn1 O5 2.110(2) . ? Zn1 N1 2.1165(18) . ? Zn1 O3 2.118(2) . ? O1 C1 1.234(3) . ? O2 C1 1.284(3) . ? O2 Zn1 1.9539(16) 1_666 ? O3 C5 1.272(3) . ? O4 C5 1.238(3) . ? N1 C4 1.489(3) . ? N1 C6 1.493(3) . ? N2 C7 1.321(4) . ? N2 C11 1.326(4) . ? C1 C2 1.516(3) . ? C2 C3 1.531(3) . ? C3 C4 1.537(3) . ? C4 C5 1.533(3) . ? C6 C9 1.508(3) . ? C7 C8 1.380(4) . ? C8 C9 1.372(4) . ? C9 C10 1.386(4) . ? C10 C11 1.378(4) . ? 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 Zn1 O6 112.23(9) 1_444 . ? O2 Zn1 O5 97.15(7) 1_444 . ? O6 Zn1 O5 86.76(9) . . ? O2 Zn1 N1 116.12(7) 1_444 . ? O6 Zn1 N1 130.36(9) . . ? O5 Zn1 N1 97.65(8) . . ? O2 Zn1 O3 96.40(7) 1_444 . ? O6 Zn1 O3 86.00(8) . . ? O5 Zn1 O3 166.26(6) . . ? N1 Zn1 O3 78.35(8) . . ? C1 O2 Zn1 126.37(16) . 1_666 ? C5 O3 Zn1 115.17(17) . . ? C4 N1 C6 106.85(17) . . ? C4 N1 Zn1 106.79(13) . . ? C6 N1 Zn1 114.55(14) . . ? C7 N2 C11 117.1(2) . . ? O1 C1 O2 125.5(2) . . ? O1 C1 C2 120.2(2) . . ? O2 C1 C2 114.3(2) . . ? C1 C2 C3 114.9(2) . . ? C2 C3 C4 110.9(2) . . ? N1 C4 C5 107.96(17) . . ? N1 C4 C3 111.86(18) . . ? C5 C4 C3 110.35(18) . . ? O4 C5 O3 123.9(2) . . ? O4 C5 C4 119.40(19) . . ? O3 C5 C4 116.7(2) . . ? N1 C6 C9 116.01(19) . . ? N2 C7 C8 123.9(3) . . ? C9 C8 C7 118.8(2) . . ? C8 C9 C10 117.9(2) . . ? C8 C9 C6 123.8(2) . . ? C10 C9 C6 118.2(2) . . ? C11 C10 C9 119.0(3) . . ? N2 C11 C10 123.3(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 O5 H5A O3 0.97 1.77 2.722(2) 169.0 1_455 O5 H5B O1 0.91 1.72 2.623(3) 171.9 1_444 O5 H5B O2 0.91 2.55 3.049(3) 115.3 1_444 O6 H6C O4 0.92 1.81 2.681(2) 156.2 1_445 O6 H6D N2 0.88 1.78 2.657(3) 173.8 1_656 N1 H1A O4 0.92 2.06 2.972(3) 170.4 1_455 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.79 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.167 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.049