Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ; Two- and Three-Dimensional Divalent Metal Coordination Polymers Constructed from 2,2-Dimethylsuccinate and Dipyridylamine Ligands ; _publ_contact_author_name 'Robert LaDuca' _publ_contact_author_email LADUCA@MSU.EDU loop_ _publ_author_name R.LaDuca K.A.Brown D.P.Martin R.M.Supkowski # Attachment '0cddmsucdpafinal.cif' data_ortho4 _database_code_depnum_ccdc_archive 'CCDC 660714' _audit_update_record ; 2008-01-30 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Cd N3 O4' _chemical_formula_weight 427.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 17.076(10) _cell_length_b 16.577(9) _cell_length_c 11.809(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3343(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 1.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _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 18038 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.21 _reflns_number_total 3883 _reflns_number_gt 2965 _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. N---H bond distances for the amine groups were restrained at 0.89(2) \%A. C---C bond distances for the disordered dimethylsuccinate methyl groups were restrained at 1.55(2) \%A. Restraints improved the refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+14.7920P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.34(6) _refine_ls_number_reflns 3883 _refine_ls_number_parameters 203 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.36542(2) 0.922805(19) 0.96425(11) 0.03354(12) Uani 1 1 d . . . O1 O 0.1189(3) 1.2593(2) 0.9707(15) 0.0569(15) Uani 1 1 d . . . O2 O 0.2261(3) 1.3302(3) 0.9555(17) 0.112(3) Uani 1 1 d . . . O3 O 0.3799(3) 1.0661(3) 0.9599(13) 0.0709(18) Uani 1 1 d . . . O4 O 0.2685(3) 1.0156(3) 0.9183(7) 0.103(4) Uani 1 1 d . . . N1 N 0.4226(6) 0.9093(5) 0.7910(9) 0.044(2) Uani 1 1 d . . . N2 N 0.4976(3) 0.8587(3) 0.4607(10) 0.0431(12) Uani 1 1 d D . . H2N H 0.541(2) 0.830(3) 0.476(8) 0.052 Uiso 1 1 d D . . N3 N 0.4140(6) 0.9107(5) 0.1385(9) 0.039(2) Uani 1 1 d . . . C1 C 0.4759(5) 0.8512(5) 0.7719(6) 0.0446(19) Uani 1 1 d . . . H1 H 0.4965 0.8224 0.8325 0.053 Uiso 1 1 calc R . . C2 C 0.5007(4) 0.8336(5) 0.6613(6) 0.0413(16) Uani 1 1 d . . . H2 H 0.5375 0.7933 0.6482 0.050 Uiso 1 1 calc R . . C3 C 0.4704(6) 0.8761(5) 0.5745(8) 0.035(2) Uani 1 1 d . . . C4 C 0.4137(5) 0.9362(4) 0.5974(7) 0.0400(17) Uani 1 1 d . . . H4 H 0.3904 0.9655 0.5393 0.048 Uiso 1 1 calc R . . C5 C 0.3947(5) 0.9492(5) 0.7068(8) 0.049(2) Uani 1 1 d . . . H5 H 0.3589 0.9900 0.7225 0.058 Uiso 1 1 calc R . . C6 C 0.3657(5) 0.9120(6) 0.2295(7) 0.052(2) Uani 1 1 d . . . H6 H 0.3133 0.9248 0.2170 0.063 Uiso 1 1 calc R . . C7 C 0.3882(5) 0.8958(6) 0.3391(7) 0.053(2) Uani 1 1 d . . . H7 H 0.3515 0.8961 0.3973 0.063 Uiso 1 1 calc R . . C8 C 0.4676(7) 0.8787(6) 0.3622(8) 0.038(3) Uani 1 1 d . . . C9 C 0.5178(4) 0.8803(5) 0.2684(6) 0.0461(18) Uani 1 1 d . . . H9 H 0.5711 0.8712 0.2778 0.055 Uiso 1 1 calc R . . C10 C 0.4886(5) 0.8951(5) 0.1647(6) 0.0441(18) Uani 1 1 d . . . H10 H 0.5240 0.8943 0.1049 0.053 Uiso 1 1 calc R . . C11 C 0.1909(5) 1.2651(4) 0.9931(6) 0.0595(11) Uani 1 1 d . . . C12 C 0.2436(5) 1.1894(5) 1.0231(7) 0.0595(11) Uani 1 1 d D . . C13 C 0.2732(6) 1.1579(5) 0.9170(7) 0.0595(11) Uani 1 1 d . . . H13A H 0.3134 1.1911 0.8825 0.071 Uiso 1 1 calc R . . H13B H 0.2327 1.1440 0.8628 0.071 Uiso 1 1 calc R . . C14 C 0.3104(5) 1.0738(4) 0.9943(6) 0.0595(11) Uani 1 1 d . . . C15 C 0.2038(8) 1.1346(7) 1.1073(12) 0.130(6) Uani 1 1 d D . . H15A H 0.1954 1.1633 1.1768 0.195 Uiso 1 1 calc R . . H15B H 0.2364 1.0885 1.1214 0.195 Uiso 1 1 calc R . . H15C H 0.1544 1.1172 1.0772 0.195 Uiso 1 1 calc R . . C16 C 0.3248(8) 1.2164(6) 1.0786(17) 0.171(9) Uani 1 1 d D . . H16A H 0.3157 1.2349 1.1545 0.256 Uiso 1 1 calc R . . H16B H 0.3473 1.2592 1.0346 0.256 Uiso 1 1 calc R . . H16C H 0.3600 1.1713 1.0800 0.256 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 0.0387(2) 0.02833(17) 0.03363(18) 0.0006(4) 0.0006(4) 0.00205(16) O1 0.058(3) 0.034(2) 0.079(4) 0.006(5) -0.005(5) -0.0007(17) O2 0.047(3) 0.032(2) 0.257(10) 0.032(7) 0.021(10) 0.003(2) O3 0.068(4) 0.048(3) 0.097(4) 0.005(6) 0.045(6) 0.003(2) O4 0.050(4) 0.044(3) 0.214(11) -0.005(4) -0.033(4) 0.001(3) N1 0.058(6) 0.036(4) 0.039(6) 0.007(4) -0.006(4) 0.006(4) N2 0.042(3) 0.052(3) 0.036(3) 0.005(5) 0.018(6) 0.012(2) N3 0.041(5) 0.036(4) 0.039(6) 0.011(4) -0.006(4) 0.000(3) C1 0.045(5) 0.052(4) 0.037(4) 0.014(4) 0.005(3) 0.021(4) C2 0.028(4) 0.053(4) 0.043(4) -0.002(4) -0.003(3) 0.007(3) C3 0.029(5) 0.042(6) 0.033(6) -0.012(4) 0.014(4) 0.001(4) C4 0.043(5) 0.040(4) 0.036(4) 0.007(3) 0.002(3) 0.009(3) C5 0.055(6) 0.037(4) 0.054(5) 0.009(4) 0.014(4) 0.019(4) C6 0.036(5) 0.080(7) 0.041(4) -0.007(4) 0.003(3) 0.007(4) C7 0.045(5) 0.076(6) 0.038(4) 0.002(4) 0.011(3) 0.000(4) C8 0.047(7) 0.039(6) 0.030(6) -0.017(4) 0.014(4) -0.014(4) C9 0.024(4) 0.076(6) 0.039(4) 0.009(4) 0.004(3) 0.007(4) C10 0.042(5) 0.056(5) 0.034(4) -0.005(4) 0.017(3) 0.011(4) C11 0.071(3) 0.041(2) 0.066(3) 0.0063(17) 0.013(2) 0.0126(19) C12 0.071(3) 0.041(2) 0.066(3) 0.0063(17) 0.013(2) 0.0126(19) C13 0.071(3) 0.041(2) 0.066(3) 0.0063(17) 0.013(2) 0.0126(19) C14 0.071(3) 0.041(2) 0.066(3) 0.0063(17) 0.013(2) 0.0126(19) C15 0.147(12) 0.102(9) 0.140(11) 0.073(8) 0.078(9) 0.077(9) C16 0.137(12) 0.050(6) 0.33(2) -0.043(10) -0.160(14) 0.019(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2 2.194(5) 4_545 ? Cd1 N3 2.228(10) 1_556 ? Cd1 N1 2.278(11) . ? Cd1 O4 2.325(6) . ? Cd1 O3 2.389(5) . ? Cd1 O1 2.724(4) 4_545 ? O1 C11 1.260(10) . ? O2 C11 1.313(10) . ? O3 C14 1.261(10) . ? O4 C14 1.500(10) . ? N1 C5 1.286(13) . ? N1 C1 1.345(11) . ? N2 C8 1.313(14) . ? N2 C3 1.450(13) . ? N3 C10 1.336(12) . ? N3 C6 1.355(13) . ? C1 C2 1.404(10) . ? C2 C3 1.348(12) . ? C3 C4 1.415(11) . ? C4 C5 1.350(11) . ? C6 C7 1.377(12) . ? C7 C8 1.412(15) . ? C8 C9 1.401(12) . ? C9 C10 1.344(10) . ? C11 C12 1.585(11) . ? C12 C13 1.448(10) . ? C12 C15 1.508(11) . ? C12 C16 1.598(11) . ? C13 C14 1.782(11) . ? 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 N3 104.2(5) 4_545 1_556 ? O2 Cd1 N1 101.2(6) 4_545 . ? N3 Cd1 N1 131.4(2) 1_556 . ? O2 Cd1 O4 86.8(2) 4_545 . ? N3 Cd1 O4 122.7(3) 1_556 . ? N1 Cd1 O4 99.2(3) . . ? O2 Cd1 O3 140.3(2) 4_545 . ? N3 Cd1 O3 94.1(4) 1_556 . ? N1 Cd1 O3 92.0(4) . . ? O4 Cd1 O3 53.9(2) . . ? O2 Cd1 O1 51.30(16) 4_545 4_545 ? N3 Cd1 O1 81.2(4) 1_556 4_545 ? N1 Cd1 O1 83.4(4) . 4_545 ? O4 Cd1 O1 137.3(2) . 4_545 ? O3 Cd1 O1 168.42(18) . 4_545 ? C11 O2 Cd1 103.4(5) . 4 ? C14 O3 Cd1 89.8(4) . . ? C14 O4 Cd1 86.9(4) . . ? C5 N1 C1 119.3(10) . . ? C5 N1 Cd1 119.0(7) . . ? C1 N1 Cd1 120.8(6) . . ? C8 N2 C3 130.2(5) . . ? C10 N3 C6 113.6(9) . . ? C10 N3 Cd1 125.9(7) . 1_554 ? C6 N3 Cd1 120.2(7) . 1_554 ? N1 C1 C2 120.6(8) . . ? C3 C2 C1 118.9(7) . . ? C2 C3 C4 119.0(8) . . ? C2 C3 N2 118.6(8) . . ? C4 C3 N2 122.4(8) . . ? C5 C4 C3 117.4(8) . . ? N1 C5 C4 124.7(8) . . ? N3 C6 C7 124.8(9) . . ? C6 C7 C8 119.3(8) . . ? N2 C8 C9 117.9(9) . . ? N2 C8 C7 126.6(9) . . ? C9 C8 C7 115.5(9) . . ? C10 C9 C8 119.8(8) . . ? N3 C10 C9 126.8(8) . . ? O1 C11 O2 116.0(8) . . ? O1 C11 C12 122.7(7) . . ? O2 C11 C12 117.8(7) . . ? C13 C12 C15 120.7(8) . . ? C13 C12 C11 106.9(6) . . ? C15 C12 C11 111.6(7) . . ? C13 C12 C16 98.8(10) . . ? C15 C12 C16 106.8(11) . . ? C11 C12 C16 111.3(7) . . ? C12 C13 C14 87.9(5) . . ? O3 C14 O4 101.1(8) . . ? O3 C14 C13 104.5(7) . . ? O4 C14 C13 91.5(6) . . ? O3 C14 Cd1 62.3(3) . . ? O4 C14 Cd1 59.4(3) . . ? C13 C14 Cd1 141.5(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 _geom_hbond_publ_flag N2 H2N O1 0.90(2) 1.99(3) 2.853(7) 159(7) 7_564 . _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.741 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.108 # Attachment '0codimsucdpafinal.cif' data_mono _database_code_depnum_ccdc_archive 'CCDC 660715' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 Co2 N6 O8' _chemical_formula_weight 748.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.831(4) _cell_length_b 10.984(2) _cell_length_c 19.584(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.956(3) _cell_angle_gamma 90.00 _cell_volume 3282.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 1.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.811 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 36436 _diffrn_reflns_av_R_equivalents 0.1096 _diffrn_reflns_av_sigmaI/netI 0.1163 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.23 _reflns_number_total 7622 _reflns_number_gt 3827 _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. N---H bond distances for the amine groups were restrained at 0.89(2) \%A. C---C bond distances for the disordered dimethylsuccinate methyl groups were restrained at 1.55(2) \%A. Restraints improved the refinement. ; _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^)+(0.0785P)^2^+4.6351P] 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 7622 _refine_ls_number_parameters 457 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.1944 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.034 _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 0.68394(4) -0.00208(7) 0.14321(4) 0.0287(2) Uani 1 1 d . . . Co2 Co 0.77689(5) -0.48909(7) -0.18381(4) 0.0313(2) Uani 1 1 d . . . O1 O 0.6921(3) -0.1540(4) 0.0929(2) 0.0502(12) Uani 1 1 d . . . O2 O 0.7885(3) -0.0472(4) 0.0705(2) 0.0470(11) Uani 1 1 d . . . O3 O 0.6812(3) -0.4559(4) -0.0986(2) 0.0452(11) Uani 1 1 d . . . O4 O 0.7706(3) -0.3438(4) -0.1271(3) 0.0538(12) Uani 1 1 d . . . O5 O 0.6164(3) 0.1338(4) 0.2209(3) 0.0574(12) Uani 1 1 d . . . O6 O 0.5873(3) -0.0466(4) 0.1687(3) 0.0531(12) Uani 1 1 d . . . O7 O 0.3326(3) -0.0312(5) 0.2464(3) 0.0691(15) Uani 1 1 d . . . O8 O 0.4369(3) -0.0569(5) 0.3565(3) 0.0726(15) Uani 1 1 d . B . N1 N 0.6563(3) -0.5316(4) -0.2672(3) 0.0359(12) Uani 1 1 d . . . N2 N 0.4165(3) -0.5890(4) -0.4521(3) 0.0417(12) Uani 1 1 d D . . H2N H 0.379(3) -0.532(4) -0.453(3) 0.050 Uiso 1 1 d D . . N3 N 0.3246(3) -0.8646(4) -0.6138(2) 0.0347(11) Uani 1 1 d . . . N4 N 0.6404(3) 0.1409(4) 0.0701(3) 0.0367(11) Uani 1 1 d . . . N5 N 0.5416(3) 0.4289(4) -0.0825(3) 0.0405(12) Uani 1 1 d D . . H5N H 0.582(3) 0.472(4) -0.090(3) 0.049 Uiso 1 1 d D . . N6 N 0.2994(3) 0.4798(4) -0.2648(2) 0.0315(11) Uani 1 1 d . . . C1 C 0.5813(4) -0.4776(5) -0.2748(3) 0.0434(16) Uani 1 1 d . . . H1 H 0.5833 -0.4227 -0.2367 0.052 Uiso 1 1 calc R . . C2 C 0.5033(4) -0.4973(5) -0.3337(3) 0.0443(15) Uani 1 1 d . . . H2 H 0.4524 -0.4570 -0.3357 0.053 Uiso 1 1 calc R . . C3 C 0.4968(4) -0.5761(5) -0.3914(3) 0.0355(14) Uani 1 1 d . . . C4 C 0.5743(4) -0.6327(5) -0.3836(3) 0.0411(15) Uani 1 1 d . . . H4 H 0.5741 -0.6885 -0.4207 0.049 Uiso 1 1 calc R . . C5 C 0.6503(4) -0.6073(5) -0.3222(3) 0.0369(14) Uani 1 1 d . . . H5 H 0.7024 -0.6462 -0.3185 0.044 Uiso 1 1 calc R . . C6 C 0.2903(4) -0.7528(5) -0.6267(3) 0.0378(14) Uani 1 1 d . . . H6 H 0.2428 -0.7363 -0.6739 0.045 Uiso 1 1 calc R . . C7 C 0.3207(4) -0.6607(5) -0.5748(3) 0.0413(15) Uani 1 1 d . . . H7 H 0.2944 -0.5824 -0.5865 0.050 Uiso 1 1 calc R . . C8 C 0.3897(4) -0.6815(5) -0.5050(3) 0.0351(13) Uani 1 1 d . . . C9 C 0.4244(4) -0.7974(5) -0.4920(3) 0.0406(15) Uani 1 1 d . . . H9 H 0.4715 -0.8166 -0.4451 0.049 Uiso 1 1 calc R . . C10 C 0.3911(4) -0.8849(6) -0.5466(3) 0.0444(16) Uani 1 1 d . . . H10 H 0.4165 -0.9638 -0.5363 0.053 Uiso 1 1 calc R . . C11 C 0.6923(4) 0.2127(5) 0.0503(3) 0.0357(14) Uani 1 1 d . . . H11 H 0.7535 0.1971 0.0723 0.043 Uiso 1 1 calc R . . C12 C 0.6619(3) 0.3053(5) 0.0011(3) 0.0352(14) Uani 1 1 d . . . H12 H 0.7015 0.3530 -0.0108 0.042 Uiso 1 1 calc R . . C13 C 0.5721(4) 0.3319(5) -0.0328(3) 0.0327(13) Uani 1 1 d . . . C14 C 0.5188(4) 0.2591(6) -0.0108(3) 0.0404(15) Uani 1 1 d . . . H14 H 0.4575 0.2737 -0.0307 0.049 Uiso 1 1 calc R . . C15 C 0.5552(4) 0.1676(6) 0.0392(3) 0.0409(15) Uani 1 1 d . . . H15 H 0.5175 0.1194 0.0531 0.049 Uiso 1 1 calc R . . C16 C 0.3224(4) 0.3723(5) -0.2313(3) 0.0381(14) Uani 1 1 d . . . H16 H 0.2820 0.3070 -0.2505 0.046 Uiso 1 1 calc R . . C17 C 0.4001(4) 0.3491(5) -0.1711(3) 0.0378(14) Uani 1 1 d . . . H17 H 0.4134 0.2695 -0.1504 0.045 Uiso 1 1 calc R . . C18 C 0.4589(3) 0.4430(5) -0.1409(3) 0.0291(12) Uani 1 1 d . . . C19 C 0.4359(4) 0.5561(5) -0.1744(3) 0.0342(13) Uani 1 1 d . . . H19 H 0.4746 0.6232 -0.1550 0.041 Uiso 1 1 calc R . . C20 C 0.3583(4) 0.5711(5) -0.2350(3) 0.0325(13) Uani 1 1 d . . . H20 H 0.3444 0.6493 -0.2577 0.039 Uiso 1 1 calc R . . C21 C 0.7508(4) -0.1455(6) 0.0680(4) 0.0469(16) Uani 1 1 d . . . C22 C 0.7721(4) -0.2664(6) 0.0335(4) 0.0532(18) Uani 1 1 d . . . C23 C 0.7116(4) -0.2503(6) -0.0473(4) 0.0571(19) Uani 1 1 d . . . H23A H 0.7254 -0.1736 -0.0665 0.069 Uiso 1 1 calc R . . H23B H 0.6504 -0.2458 -0.0530 0.069 Uiso 1 1 calc R . . C24 C 0.7222(4) -0.3602(6) -0.0930(4) 0.0441(16) Uani 1 1 d . . . C25 C 0.8682(4) -0.2651(6) 0.0463(4) 0.0565(19) Uani 1 1 d . . . H25A H 0.9057 -0.2761 0.1001 0.085 Uiso 1 1 calc R . . H25B H 0.8818 -0.1870 0.0295 0.085 Uiso 1 1 calc R . . H25C H 0.8787 -0.3314 0.0177 0.085 Uiso 1 1 calc R . . C26 C 0.7521(5) -0.3793(5) 0.0676(4) 0.0571(19) Uani 1 1 d . . . H26A H 0.7937 -0.3855 0.1206 0.086 Uiso 1 1 calc R . . H26B H 0.7573 -0.4513 0.0402 0.086 Uiso 1 1 calc R . . H26C H 0.6923 -0.3740 0.0640 0.086 Uiso 1 1 calc R . . C31 C 0.5729(5) 0.0426(7) 0.2048(4) 0.0539(18) Uani 1 1 d . B . C32 C 0.4883(6) 0.0365(8) 0.2196(6) 0.090(3) Uani 1 1 d D . . C33 C 0.4796(5) -0.0736(10) 0.2540(5) 0.089(3) Uani 1 1 d D A . C34 C 0.4115(5) -0.0503(7) 0.2880(4) 0.0560(19) Uani 1 1 d . . . C35 C 0.5599(7) -0.1337(12) 0.3074(7) 0.068(4) Uani 0.60 1 d PD A 1 H35A H 0.5445 -0.2099 0.3249 0.102 Uiso 0.60 1 calc PR A 1 H35B H 0.5905 -0.0800 0.3505 0.102 Uiso 0.60 1 calc PR A 1 H35C H 0.5982 -0.1514 0.2823 0.102 Uiso 0.60 1 calc PR A 1 C36 C 0.4338(9) -0.1622(15) 0.1842(8) 0.097(6) Uani 0.60 1 d PD A 1 H36A H 0.4244 -0.2419 0.2021 0.146 Uiso 0.60 1 calc PR A 1 H36B H 0.4714 -0.1715 0.1576 0.146 Uiso 0.60 1 calc PR A 1 H36C H 0.3772 -0.1278 0.1499 0.146 Uiso 0.60 1 calc PR A 1 C35A C 0.4523(12) 0.1541(14) 0.2302(11) 0.066(5) Uani 0.40 1 d PD B 2 H35D H 0.4670 0.2179 0.2025 0.099 Uiso 0.40 1 calc PR B 2 H35E H 0.4776 0.1745 0.2839 0.099 Uiso 0.40 1 calc PR B 2 H35F H 0.3885 0.1477 0.2113 0.099 Uiso 0.40 1 calc PR B 2 C36A C 0.4119(10) -0.0236(18) 0.1422(10) 0.070(6) Uani 0.40 1 d PD B 2 H36D H 0.3963 0.0345 0.1006 0.104 Uiso 0.40 1 calc PR B 2 H36E H 0.3599 -0.0425 0.1507 0.104 Uiso 0.40 1 calc PR B 2 H36F H 0.4344 -0.0985 0.1295 0.104 Uiso 0.40 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0286(4) 0.0316(4) 0.0277(4) -0.0019(3) 0.0136(3) -0.0055(3) Co2 0.0300(4) 0.0368(5) 0.0267(4) -0.0030(3) 0.0115(3) -0.0004(4) O1 0.048(3) 0.055(3) 0.065(3) -0.026(2) 0.040(2) -0.022(2) O2 0.045(3) 0.042(2) 0.061(3) -0.011(2) 0.030(2) -0.014(2) O3 0.053(3) 0.048(2) 0.044(3) -0.017(2) 0.029(2) -0.031(2) O4 0.070(3) 0.043(3) 0.079(3) -0.019(2) 0.062(3) -0.022(2) O5 0.058(3) 0.056(3) 0.070(3) -0.009(3) 0.039(3) -0.010(2) O6 0.068(3) 0.047(3) 0.069(3) -0.008(2) 0.053(3) -0.012(2) O7 0.042(3) 0.122(5) 0.048(3) -0.002(3) 0.023(2) -0.002(3) O8 0.075(4) 0.097(4) 0.061(3) 0.019(3) 0.044(3) 0.033(3) N1 0.037(3) 0.038(3) 0.032(3) -0.002(2) 0.014(2) 0.009(2) N2 0.029(3) 0.046(3) 0.042(3) -0.011(3) 0.007(2) 0.008(2) N3 0.027(3) 0.044(3) 0.026(3) 0.004(2) 0.004(2) 0.005(2) N4 0.026(3) 0.043(3) 0.041(3) 0.007(2) 0.015(2) -0.002(2) N5 0.035(3) 0.043(3) 0.043(3) 0.012(2) 0.016(3) -0.007(2) N6 0.029(2) 0.027(3) 0.035(3) 0.005(2) 0.010(2) 0.004(2) C1 0.040(4) 0.054(4) 0.037(3) -0.011(3) 0.017(3) 0.013(3) C2 0.028(3) 0.058(4) 0.042(3) -0.011(3) 0.010(3) 0.013(3) C3 0.034(3) 0.047(4) 0.025(3) -0.006(3) 0.012(3) 0.004(3) C4 0.037(4) 0.043(4) 0.044(4) -0.018(3) 0.017(3) 0.002(3) C5 0.029(3) 0.042(3) 0.041(3) -0.013(3) 0.016(3) 0.003(3) C6 0.029(3) 0.038(3) 0.033(3) 0.004(3) 0.001(3) 0.002(3) C7 0.029(3) 0.037(3) 0.047(4) 0.000(3) 0.007(3) 0.007(3) C8 0.029(3) 0.039(3) 0.035(3) -0.004(3) 0.011(3) 0.001(3) C9 0.033(3) 0.040(3) 0.031(3) -0.005(3) -0.004(3) 0.001(3) C10 0.033(3) 0.042(4) 0.041(4) 0.002(3) -0.001(3) 0.012(3) C11 0.025(3) 0.043(3) 0.040(3) 0.008(3) 0.014(3) -0.003(3) C12 0.029(3) 0.040(3) 0.042(3) 0.005(3) 0.020(3) -0.008(3) C13 0.032(3) 0.038(3) 0.029(3) 0.001(2) 0.013(3) -0.008(3) C14 0.024(3) 0.060(4) 0.038(3) 0.015(3) 0.013(3) -0.004(3) C15 0.028(3) 0.059(4) 0.041(4) 0.014(3) 0.020(3) -0.002(3) C16 0.032(3) 0.034(3) 0.041(4) 0.005(3) 0.008(3) -0.007(3) C17 0.035(3) 0.028(3) 0.044(4) 0.012(3) 0.011(3) -0.004(3) C18 0.023(3) 0.040(3) 0.024(3) 0.003(2) 0.010(2) -0.003(2) C19 0.033(3) 0.039(3) 0.028(3) -0.002(3) 0.011(3) -0.006(3) C20 0.036(3) 0.027(3) 0.038(3) 0.003(2) 0.018(3) 0.000(3) C21 0.045(4) 0.054(4) 0.054(4) -0.021(3) 0.034(3) -0.016(3) C22 0.036(4) 0.066(5) 0.056(4) 0.017(4) 0.018(3) 0.001(3) C23 0.041(4) 0.078(5) 0.060(5) 0.017(4) 0.029(4) -0.002(4) C24 0.043(4) 0.045(4) 0.053(4) -0.014(3) 0.029(3) -0.011(3) C25 0.035(4) 0.077(5) 0.058(4) -0.025(4) 0.021(3) -0.003(3) C26 0.088(6) 0.041(4) 0.050(4) 0.006(3) 0.036(4) 0.003(4) C31 0.069(5) 0.056(4) 0.063(5) -0.005(4) 0.055(4) -0.006(4) C32 0.104(7) 0.070(6) 0.127(9) -0.005(5) 0.078(7) -0.018(5) C33 0.075(6) 0.132(9) 0.082(6) 0.018(6) 0.053(5) 0.001(6) C34 0.041(4) 0.094(5) 0.043(4) -0.003(4) 0.026(4) -0.009(4) C35 0.038(7) 0.096(10) 0.076(9) 0.034(8) 0.030(7) 0.029(7) C36 0.070(10) 0.142(14) 0.106(12) -0.087(11) 0.063(9) -0.041(10) C35A 0.078(14) 0.051(11) 0.091(15) -0.028(10) 0.056(12) -0.008(10) C36A 0.026(8) 0.095(15) 0.079(14) -0.050(12) 0.014(9) -0.019(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O6 1.954(4) . ? Co1 O1 1.972(4) . ? Co1 N6 2.032(4) 4_666 ? Co1 N4 2.042(5) . ? Co2 O7 1.970(4) 4_655 ? Co2 O4 1.973(4) . ? Co2 N3 2.043(5) 4_646 ? Co2 N1 2.051(5) . ? O1 C21 1.276(6) . ? O2 C21 1.242(7) . ? O3 C24 1.236(7) . ? O4 C24 1.265(7) . ? O5 C31 1.202(7) . ? O6 C31 1.289(7) . ? O7 C34 1.248(8) . ? O7 Co2 1.970(4) 4_556 ? O8 C34 1.227(7) . ? N1 C5 1.331(6) . ? N1 C1 1.345(7) . ? N2 C3 1.380(7) . ? N2 C8 1.384(7) . ? N3 C6 1.335(7) . ? N3 C10 1.339(7) . ? N3 Co2 2.043(5) 4_545 ? N4 C15 1.333(7) . ? N4 C11 1.350(6) . ? N5 C13 1.387(7) . ? N5 C18 1.388(7) . ? N6 C16 1.326(6) . ? N6 C20 1.357(6) . ? N6 Co1 2.032(4) 4_565 ? C1 C2 1.349(8) . ? C2 C3 1.391(7) . ? C3 C4 1.394(7) . ? C4 C5 1.365(7) . ? C6 C7 1.371(8) . ? C7 C8 1.389(7) . ? C8 C9 1.379(8) . ? C9 C10 1.369(8) . ? C11 C12 1.345(7) . ? C12 C13 1.401(7) . ? C13 C14 1.399(7) . ? C14 C15 1.356(8) . ? C16 C17 1.365(7) . ? C17 C18 1.378(7) . ? C18 C19 1.382(7) . ? C19 C20 1.354(7) . ? C21 C22 1.598(9) . ? C22 C23 1.486(9) . ? C22 C26 1.512(8) . ? C22 C25 1.528(8) . ? C23 C24 1.558(9) . ? C31 C32 1.569(10) . ? C32 C33 1.422(12) . ? C32 C35A 1.478(13) . ? C32 C36A 1.655(13) . ? C33 C35 1.470(11) . ? C33 C34 1.571(10) . ? C33 C36 1.587(12) . ? 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 99.05(17) . . ? O6 Co1 N6 113.00(19) . 4_666 ? O1 Co1 N6 107.62(18) . 4_666 ? O6 Co1 N4 106.28(19) . . ? O1 Co1 N4 112.37(19) . . ? N6 Co1 N4 117.10(18) 4_666 . ? O7 Co2 O4 117.0(2) 4_655 . ? O7 Co2 N3 112.8(2) 4_655 4_646 ? O4 Co2 N3 110.97(19) . 4_646 ? O7 Co2 N1 94.24(19) 4_655 . ? O4 Co2 N1 111.24(19) . . ? N3 Co2 N1 109.38(18) 4_646 . ? C21 O1 Co1 111.0(4) . . ? C24 O4 Co2 112.4(4) . . ? C31 O6 Co1 108.6(4) . . ? C34 O7 Co2 104.6(4) . 4_556 ? C5 N1 C1 116.1(5) . . ? C5 N1 Co2 119.8(4) . . ? C1 N1 Co2 123.7(4) . . ? C3 N2 C8 127.8(5) . . ? C6 N3 C10 117.0(5) . . ? C6 N3 Co2 125.5(4) . 4_545 ? C10 N3 Co2 117.2(4) . 4_545 ? C15 N4 C11 116.3(5) . . ? C15 N4 Co1 119.1(4) . . ? C11 N4 Co1 124.5(4) . . ? C13 N5 C18 127.5(5) . . ? C16 N6 C20 115.9(5) . . ? C16 N6 Co1 121.1(4) . 4_565 ? C20 N6 Co1 123.0(4) . 4_565 ? N1 C1 C2 123.6(5) . . ? C1 C2 C3 120.5(5) . . ? N2 C3 C2 118.5(5) . . ? N2 C3 C4 125.4(5) . . ? C2 C3 C4 116.1(5) . . ? C5 C4 C3 119.4(5) . . ? N1 C5 C4 124.2(5) . . ? N3 C6 C7 122.9(5) . . ? C6 C7 C8 120.2(5) . . ? C9 C8 N2 124.1(5) . . ? C9 C8 C7 116.5(5) . . ? N2 C8 C7 119.3(5) . . ? C10 C9 C8 120.1(5) . . ? N3 C10 C9 123.2(5) . . ? C12 C11 N4 123.4(5) . . ? C11 C12 C13 120.3(5) . . ? N5 C13 C14 124.1(5) . . ? N5 C13 C12 119.8(5) . . ? C14 C13 C12 116.1(5) . . ? C15 C14 C13 119.5(5) . . ? N4 C15 C14 124.3(5) . . ? N6 C16 C17 124.5(5) . . ? C16 C17 C18 118.9(5) . . ? C17 C18 C19 117.6(5) . . ? C17 C18 N5 124.0(5) . . ? C19 C18 N5 118.2(5) . . ? C20 C19 C18 119.9(5) . . ? C19 C20 N6 123.1(5) . . ? O2 C21 O1 120.8(6) . . ? O2 C21 C22 122.5(5) . . ? O1 C21 C22 116.7(5) . . ? C23 C22 C26 112.8(6) . . ? C23 C22 C25 112.1(6) . . ? C26 C22 C25 110.6(6) . . ? C23 C22 C21 100.1(5) . . ? C26 C22 C21 111.3(5) . . ? C25 C22 C21 109.5(5) . . ? C22 C23 C24 109.1(6) . . ? O3 C24 O4 122.3(6) . . ? O3 C24 C23 121.0(5) . . ? O4 C24 C23 116.6(5) . . ? O5 C31 O6 122.8(6) . . ? O5 C31 C32 119.2(6) . . ? O6 C31 C32 117.6(6) . . ? C33 C32 C35A 123.1(10) . . ? C33 C32 C31 113.9(8) . . ? C35A C32 C31 116.5(9) . . ? C33 C32 C36A 84.2(10) . . ? C35A C32 C36A 105.7(12) . . ? C31 C32 C36A 105.3(8) . . ? C32 C33 C35 118.2(9) . . ? C32 C33 C34 107.5(8) . . ? C35 C33 C34 112.8(7) . . ? C32 C33 C36 102.9(9) . . ? C35 C33 C36 107.7(11) . . ? C34 C33 C36 106.7(7) . . ? O8 C34 O7 120.5(6) . . ? O8 C34 C33 118.3(6) . . ? O7 C34 C33 121.1(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O2 0.89(2) 1.97(3) 2.808(6) 158(6) 4 N5 H5N O3 0.89(2) 1.92(2) 2.801(6) 171(6) 1_565 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.886 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.104 # Attachment '0cudimsdpa.cif' data_ortho_0cudimsdpa _database_code_depnum_ccdc_archive 'CCDC 660716' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Cu N3 O4' _chemical_formula_weight 378.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Cmca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 11.664(3) _cell_length_b 15.697(5) _cell_length_c 17.263(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3160.7(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 1.408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _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 16814 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1960 _reflns_number_gt 1805 _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^)+(0.0000P)^2^+23.3820P] 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 1960 _refine_ls_number_parameters 126 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.240 _refine_ls_restrained_S_all 1.240 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.06328(3) 0.37095(3) 0.02055(16) Uani 1 2 d S . . O1 O 0.5000 0.1686(2) 0.3114(2) 0.0289(8) Uani 1 2 d S . . O2 O 0.5000 0.2459(2) 0.4191(2) 0.0373(9) Uani 1 2 d S . . O3 O 0.5000 0.4767(2) 0.2362(2) 0.0479(12) Uani 1 2 d S . . O4 O 0.5000 0.4349(2) 0.11605(19) 0.0301(8) Uani 1 2 d S . . N1 N 0.3365(2) 0.07403(17) 0.40457(16) 0.0246(6) Uani 1 1 d . . . N2 N 0.0000 0.1180(3) 0.4783(2) 0.0261(9) Uani 1 2 d SD . . H2N H 0.0000 0.155(3) 0.517(2) 0.031 Uiso 1 2 d SD . . C1 C 0.3105(3) 0.1156(3) 0.4693(2) 0.0418(10) Uani 1 1 d . . . H1 H 0.3700 0.1358 0.5001 0.050 Uiso 1 1 calc R . . C2 C 0.1998(3) 0.1300(3) 0.4929(2) 0.0428(10) Uani 1 1 d . . . H2 H 0.1862 0.1606 0.5381 0.051 Uiso 1 1 calc R . . C3 C 0.1083(3) 0.0998(2) 0.45019(19) 0.0224(6) Uani 1 1 d . . . C4 C 0.1355(3) 0.0535(3) 0.3848(3) 0.0501(12) Uani 1 1 d . . . H4 H 0.0778 0.0294 0.3547 0.060 Uiso 1 1 calc R . . C5 C 0.2488(4) 0.0431(3) 0.3645(3) 0.0487(12) Uani 1 1 d . . . H5 H 0.2650 0.0124 0.3197 0.058 Uiso 1 1 calc R . . C6 C 0.5000 0.2393(3) 0.3468(3) 0.0291(11) Uani 1 2 d S . . C7 C 0.5000 0.3218(3) 0.3011(3) 0.0499(18) Uani 1 2 d S . . H7A H 0.4333 0.3537 0.3180 0.060 Uiso 0.50 1 calc PR . . H7B H 0.5667 0.3537 0.3180 0.060 Uiso 0.50 1 calc PR . . C8 C 0.5000 0.3245(3) 0.2145(3) 0.0296(11) Uani 1 2 d S . . C9 C 0.5000 0.4182(3) 0.1883(3) 0.0230(9) Uani 1 2 d S . . C10 C 0.6033(8) 0.2824(4) 0.1814(4) 0.135(4) Uani 1 1 d . . . H10A H 0.6001 0.2849 0.1258 0.202 Uiso 1 1 calc R . . H10B H 0.6055 0.2239 0.1977 0.202 Uiso 1 1 calc R . . H10C H 0.6710 0.3111 0.1992 0.202 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0183(3) 0.0171(3) 0.0263(3) 0.0000(2) 0.000 0.000 O1 0.042(2) 0.0168(15) 0.0284(18) 0.0006(13) 0.000 0.000 O2 0.056(3) 0.0301(19) 0.0261(18) -0.0009(15) 0.000 0.000 O3 0.097(4) 0.0180(17) 0.029(2) -0.0007(15) 0.000 0.000 O4 0.042(2) 0.0229(16) 0.0260(18) 0.0017(14) 0.000 0.000 N1 0.0197(14) 0.0255(14) 0.0287(14) -0.0009(11) 0.0002(11) -0.0009(11) N2 0.0181(19) 0.032(2) 0.028(2) -0.0095(17) 0.000 0.000 C1 0.0212(18) 0.065(3) 0.039(2) -0.021(2) -0.0021(16) -0.0052(18) C2 0.0241(18) 0.067(3) 0.037(2) -0.028(2) 0.0030(16) -0.0028(18) C3 0.0187(15) 0.0218(14) 0.0268(16) 0.0020(12) 0.0012(13) 0.0010(12) C4 0.0209(18) 0.081(3) 0.049(3) -0.036(2) -0.0032(17) -0.001(2) C5 0.0243(18) 0.073(3) 0.049(2) -0.037(2) 0.0012(18) 0.000(2) C6 0.037(3) 0.023(2) 0.028(2) 0.0024(19) 0.000 0.000 C7 0.105(6) 0.015(2) 0.029(3) -0.001(2) 0.000 0.000 C8 0.043(3) 0.019(2) 0.027(2) 0.0010(19) 0.000 0.000 C9 0.023(2) 0.018(2) 0.028(2) -0.0002(17) 0.000 0.000 C10 0.191(9) 0.074(4) 0.139(6) 0.067(4) 0.121(6) 0.091(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.947(3) . ? Cu1 N1 2.000(3) . ? Cu1 N1 2.000(3) 12_655 ? Cu1 O4 2.027(3) 10_556 ? Cu1 O3 2.296(4) 10_556 ? Cu1 C9 2.496(5) 10_556 ? O1 C6 1.267(6) . ? O2 C6 1.252(6) . ? O3 C9 1.235(6) . ? O3 Cu1 2.296(4) 10_566 ? O4 C9 1.275(6) . ? O4 Cu1 2.027(3) 10_566 ? N1 C5 1.327(5) . ? N1 C1 1.329(5) . ? N2 C3 1.383(4) 12 ? N2 C3 1.383(4) . ? C1 C2 1.373(5) . ? C2 C3 1.381(5) . ? C3 C4 1.380(5) . ? C4 C5 1.378(6) . ? C6 C7 1.516(7) . ? C7 C8 1.497(7) . ? C8 C10 1.489(6) 12_655 ? C8 C10 1.489(6) . ? C8 C9 1.539(6) . ? C9 Cu1 2.496(5) 10_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 94.68(9) . . ? O1 Cu1 N1 94.68(9) . 12_655 ? N1 Cu1 N1 144.82(16) . 12_655 ? O1 Cu1 O4 154.48(14) . 10_556 ? N1 Cu1 O4 92.96(9) . 10_556 ? N1 Cu1 O4 92.96(9) 12_655 10_556 ? O1 Cu1 O3 94.42(14) . 10_556 ? N1 Cu1 O3 106.49(8) . 10_556 ? N1 Cu1 O3 106.49(8) 12_655 10_556 ? O4 Cu1 O3 60.05(13) 10_556 10_556 ? O1 Cu1 C9 123.91(15) . 10_556 ? N1 Cu1 C9 101.30(8) . 10_556 ? N1 Cu1 C9 101.30(8) 12_655 10_556 ? O4 Cu1 C9 30.56(14) 10_556 10_556 ? O3 Cu1 C9 29.49(14) 10_556 10_556 ? C6 O1 Cu1 119.2(3) . . ? C9 O3 Cu1 84.3(3) . 10_566 ? C9 O4 Cu1 95.5(3) . 10_566 ? C5 N1 C1 116.2(3) . . ? C5 N1 Cu1 123.6(2) . . ? C1 N1 Cu1 120.2(2) . . ? C3 N2 C3 131.9(4) 12 . ? N1 C1 C2 123.0(3) . . ? C1 C2 C3 120.8(3) . . ? C4 C3 C2 116.1(3) . . ? C4 C3 N2 127.3(3) . . ? C2 C3 N2 116.6(3) . . ? C5 C4 C3 119.4(4) . . ? N1 C5 C4 124.4(4) . . ? O2 C6 O1 123.6(5) . . ? O2 C6 C7 116.6(5) . . ? O1 C6 C7 119.8(5) . . ? C8 C7 C6 123.0(5) . . ? C10 C8 C10 108.1(9) 12_655 . ? C10 C8 C7 111.8(4) 12_655 . ? C10 C8 C7 111.8(4) . . ? C10 C8 C9 108.2(3) 12_655 . ? C10 C8 C9 108.2(3) . . ? C7 C8 C9 108.7(4) . . ? O3 C9 O4 120.2(4) . . ? O3 C9 C8 120.9(4) . . ? O4 C9 C8 118.9(4) . . ? O3 C9 Cu1 66.2(3) . 10_566 ? O4 C9 Cu1 53.9(2) . 10_566 ? C8 C9 Cu1 172.8(3) . 10_566 ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.486 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.091 # Attachment '0nidimsdpafinal.cif' data_ortho_0nidimsdpafinal _database_code_depnum_ccdc_archive 'CCDC 660717' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N3 Ni O4' _chemical_formula_weight 374.04 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.316(6) _cell_length_b 8.094(3) _cell_length_c 23.421(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3092.9(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 1.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.906 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _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 32441 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3679 _reflns_number_gt 2806 _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^)+(0.0310P)^2^+3.5390P] 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 3679 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 0.227867(17) 0.24507(3) 0.104493(12) 0.02098(9) Uani 1 1 d . . . O1 O 0.11688(10) 0.3010(2) 0.13219(7) 0.0318(4) Uani 1 1 d . . . O2 O -0.01031(12) 0.3501(3) 0.15555(11) 0.0604(7) Uani 1 1 d . . . O3 O 0.21020(9) -0.00261(19) 0.09863(7) 0.0234(3) Uani 1 1 d . . . O4 O 0.15011(10) -0.23486(18) 0.07738(7) 0.0255(3) Uani 1 1 d . . . N1 N 0.27208(12) 0.2020(2) 0.18747(8) 0.0265(4) Uani 1 1 d . . . N2 N 0.36570(13) 0.0891(3) 0.35002(9) 0.0318(5) Uani 1 1 d D . . H2N H 0.4094(13) 0.031(3) 0.3473(12) 0.038 Uiso 1 1 d D . . N3 N 0.30899(12) 0.2043(2) 0.52013(8) 0.0233(4) Uani 1 1 d . . . C1 C 0.22732(16) 0.2289(4) 0.23419(11) 0.0377(6) Uani 1 1 d . . . H1 H 0.1751 0.2730 0.2294 0.045 Uiso 1 1 calc R . . C2 C 0.25290(18) 0.1960(4) 0.28900(11) 0.0402(7) Uani 1 1 d . . . H2 H 0.2184 0.2162 0.3198 0.048 Uiso 1 1 calc R . . C3 C 0.33122(15) 0.1321(3) 0.29779(10) 0.0271(5) Uani 1 1 d . . . C4 C 0.37650(15) 0.0978(3) 0.24913(10) 0.0299(5) Uani 1 1 d . . . H4 H 0.4281 0.0499 0.2525 0.036 Uiso 1 1 calc R . . C5 C 0.34601(15) 0.1339(3) 0.19603(10) 0.0281(5) Uani 1 1 d . . . H5 H 0.3782 0.1099 0.1643 0.034 Uiso 1 1 calc R . . C6 C 0.36950(14) 0.1001(3) 0.50543(10) 0.0267(5) Uani 1 1 d . . . H6 H 0.3995 0.0500 0.5344 0.032 Uiso 1 1 calc R . . C7 C 0.38935(15) 0.0637(3) 0.44990(10) 0.0278(5) Uani 1 1 d . . . H7 H 0.4325 -0.0079 0.4421 0.033 Uiso 1 1 calc R . . C8 C 0.34502(14) 0.1339(3) 0.40490(9) 0.0240(5) Uani 1 1 d . . . C9 C 0.28428(15) 0.2466(3) 0.42029(11) 0.0326(6) Uani 1 1 d . . . H9 H 0.2543 0.3015 0.3923 0.039 Uiso 1 1 calc R . . C10 C 0.26903(16) 0.2759(3) 0.47723(11) 0.0316(6) Uani 1 1 d . . . H10 H 0.2279 0.3510 0.4863 0.038 Uiso 1 1 calc R . . C11 C 0.04314(15) 0.2581(3) 0.13604(10) 0.0297(5) Uani 1 1 d . . . C12 C 0.01633(15) 0.0824(3) 0.11746(13) 0.0372(6) Uani 1 1 d . . . C13 C 0.06675(14) 0.0060(3) 0.06833(11) 0.0293(5) Uani 1 1 d . . . H13A H 0.0319 -0.0727 0.0487 0.035 Uiso 1 1 calc R . . H13B H 0.0792 0.0935 0.0414 0.035 Uiso 1 1 calc R . . C14 C 0.14616(13) -0.0806(3) 0.08262(9) 0.0220(5) Uani 1 1 d . . . C15 C -0.07244(18) 0.0934(5) 0.0947(2) 0.0777(13) Uani 1 1 d . . . H15A H -0.1070 0.1416 0.1234 0.117 Uiso 1 1 calc R . . H15B H -0.0919 -0.0153 0.0856 0.117 Uiso 1 1 calc R . . H15C H -0.0735 0.1610 0.0611 0.117 Uiso 1 1 calc R . . C16 C 0.0200(3) -0.0285(5) 0.17014(17) 0.0773(13) Uani 1 1 d . . . H16A H -0.0116 0.0201 0.2004 0.116 Uiso 1 1 calc R . . H16B H 0.0759 -0.0402 0.1822 0.116 Uiso 1 1 calc R . . H16C H -0.0020 -0.1353 0.1610 0.116 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 0.02367(16) 0.02016(15) 0.01910(15) -0.00108(11) -0.00046(11) 0.00057(12) O1 0.0279(9) 0.0348(9) 0.0327(10) -0.0067(8) 0.0039(7) 0.0034(7) O2 0.0342(11) 0.0560(14) 0.0911(18) -0.0253(13) 0.0042(12) 0.0185(10) O3 0.0220(8) 0.0212(8) 0.0269(9) -0.0017(6) -0.0043(7) -0.0005(6) O4 0.0287(8) 0.0200(8) 0.0278(8) -0.0005(7) 0.0007(7) -0.0020(7) N1 0.0324(11) 0.0226(9) 0.0246(10) -0.0017(8) -0.0006(8) 0.0023(8) N2 0.0319(11) 0.0409(13) 0.0227(10) -0.0004(9) -0.0002(9) 0.0164(10) N3 0.0256(10) 0.0243(10) 0.0201(9) -0.0005(7) 0.0010(8) -0.0004(8) C1 0.0347(14) 0.0502(17) 0.0280(13) -0.0033(12) -0.0032(11) 0.0149(13) C2 0.0345(13) 0.0649(19) 0.0211(12) -0.0014(13) 0.0014(11) 0.0159(13) C3 0.0290(12) 0.0296(12) 0.0226(12) 0.0000(9) -0.0025(10) 0.0026(10) C4 0.0260(12) 0.0371(13) 0.0267(12) 0.0013(11) 0.0005(10) 0.0070(11) C5 0.0299(12) 0.0325(13) 0.0219(12) -0.0010(10) 0.0047(10) 0.0044(11) C6 0.0316(12) 0.0270(12) 0.0214(12) 0.0019(9) -0.0054(10) 0.0031(10) C7 0.0269(12) 0.0305(13) 0.0261(12) 0.0009(10) -0.0001(10) 0.0075(10) C8 0.0256(11) 0.0269(12) 0.0194(11) 0.0009(9) -0.0003(9) -0.0037(10) C9 0.0348(13) 0.0388(14) 0.0244(12) 0.0030(11) -0.0029(10) 0.0108(12) C10 0.0339(14) 0.0355(14) 0.0255(12) -0.0011(10) -0.0006(10) 0.0108(11) C11 0.0282(12) 0.0364(14) 0.0247(12) 0.0007(11) -0.0006(10) 0.0113(11) C12 0.0238(12) 0.0378(15) 0.0500(17) 0.0011(13) 0.0089(12) 0.0027(11) C13 0.0246(11) 0.0288(12) 0.0345(14) -0.0020(10) -0.0061(10) -0.0011(10) C14 0.0229(11) 0.0257(12) 0.0173(10) 0.0010(9) 0.0007(9) 0.0009(9) C15 0.0255(15) 0.076(3) 0.132(4) -0.036(3) 0.0019(19) -0.0026(16) C16 0.113(3) 0.053(2) 0.066(2) 0.0189(18) 0.054(2) 0.015(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 O1 1.9762(18) . ? Ni1 O3 2.0299(17) . ? Ni1 O4 2.0961(18) 8_665 ? Ni1 N1 2.102(2) . ? Ni1 N3 2.106(2) 2_554 ? Ni1 O3 2.2826(17) 8_665 ? O1 C11 1.255(3) . ? O2 C11 1.234(3) . ? O3 C14 1.277(3) . ? O3 Ni1 2.2827(17) 8_655 ? O4 C14 1.257(3) . ? O4 Ni1 2.0960(18) 8_655 ? N1 C1 1.333(3) . ? N1 C5 1.341(3) . ? N2 C8 1.378(3) . ? N2 C3 1.390(3) . ? N3 C10 1.331(3) . ? N3 C6 1.343(3) . ? N3 Ni1 2.105(2) 2 ? C1 C2 1.376(4) . ? C2 C3 1.394(4) . ? C3 C4 1.386(3) . ? C4 C5 1.371(3) . ? C6 C7 1.372(3) . ? C7 C8 1.399(3) . ? C8 C9 1.394(3) . ? C9 C10 1.377(4) . ? C11 C12 1.550(4) . ? C12 C16 1.527(5) . ? C12 C13 1.544(4) . ? C12 C15 1.546(4) . ? C13 C14 1.510(3) . ? 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 Ni1 O3 96.79(7) . . ? O1 Ni1 O4 162.20(7) . 8_665 ? O3 Ni1 O4 101.01(6) . 8_665 ? O1 Ni1 N1 92.81(8) . . ? O3 Ni1 N1 86.99(7) . . ? O4 Ni1 N1 88.11(7) 8_665 . ? O1 Ni1 N3 90.09(8) . 2_554 ? O3 Ni1 N3 95.06(7) . 2_554 ? O4 Ni1 N3 88.39(7) 8_665 2_554 ? N1 Ni1 N3 176.23(8) . 2_554 ? O1 Ni1 O3 102.74(7) . 8_665 ? O3 Ni1 O3 160.45(4) . 8_665 ? O4 Ni1 O3 59.47(6) 8_665 8_665 ? N1 Ni1 O3 92.98(7) . 8_665 ? N3 Ni1 O3 84.02(7) 2_554 8_665 ? C11 O1 Ni1 146.98(17) . . ? C14 O3 Ni1 128.61(14) . . ? C14 O3 Ni1 86.44(13) . 8_655 ? Ni1 O3 Ni1 144.74(8) . 8_655 ? C14 O4 Ni1 95.52(14) . 8_655 ? C1 N1 C5 115.9(2) . . ? C1 N1 Ni1 122.93(17) . . ? C5 N1 Ni1 121.00(16) . . ? C8 N2 C3 131.0(2) . . ? C10 N3 C6 116.1(2) . . ? C10 N3 Ni1 118.94(16) . 2 ? C6 N3 Ni1 124.94(15) . 2 ? N1 C1 C2 124.6(2) . . ? C1 C2 C3 119.2(2) . . ? C4 C3 N2 117.2(2) . . ? C4 C3 C2 116.2(2) . . ? N2 C3 C2 126.4(2) . . ? C5 C4 C3 120.7(2) . . ? N1 C5 C4 123.3(2) . . ? N3 C6 C7 123.4(2) . . ? C6 C7 C8 120.3(2) . . ? N2 C8 C9 126.0(2) . . ? N2 C8 C7 118.0(2) . . ? C9 C8 C7 116.0(2) . . ? C10 C9 C8 119.4(2) . . ? N3 C10 C9 124.6(2) . . ? O2 C11 O1 122.5(3) . . ? O2 C11 C12 117.2(2) . . ? O1 C11 C12 120.3(2) . . ? C16 C12 C13 110.2(2) . . ? C16 C12 C15 110.4(3) . . ? C13 C12 C15 105.4(3) . . ? C16 C12 C11 107.6(3) . . ? C13 C12 C11 115.2(2) . . ? C15 C12 C11 107.9(2) . . ? C14 C13 C12 118.5(2) . . ? O4 C14 O3 118.5(2) . . ? O4 C14 C13 118.9(2) . . ? O3 C14 C13 122.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O2 0.856(17) 1.967(19) 2.802(3) 165(3) 6_656 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.433 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.067