# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Wolfgang Schmitt' 'Rodolphe Clerac' 'Nigel G. R. Hearns' 'Paul E. Kruger' 'David P. Walsh' _publ_contact_author_name 'Wolfgang Schmitt' _publ_contact_author_email SCHMITTW@TCD.IE _publ_section_title ; Modulating Topologies and Magnetic Properties of Coordination Polymers using 2,2-Bipyridine and 5-Aminodiacetic Isophthalic Acid as Ligands ; # Attachment 'Compound1.CIF' data_dwcu2m _database_code_depnum_ccdc_archive 'CCDC 718745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 Co2 N3 O15' _chemical_formula_weight 693.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1987(7) _cell_length_b 12.1765(8) _cell_length_c 12.6676(8) _cell_angle_alpha 103.8970(10) _cell_angle_beta 105.9730(10) _cell_angle_gamma 107.5480(10) _cell_volume 1349.43(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 114 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.27 _exptl_crystal_description plates _exptl_crystal_colour pink _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 1.310 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 18836 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6713 _reflns_number_gt 6024 _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^)+(0.0604P)^2^+0.8475P] 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 6713 _refine_ls_number_parameters 427 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co -0.43233(3) -0.53945(2) 0.39977(2) 0.01446(8) Uani 1 1 d . . . Co2 Co 0.18759(3) -0.14002(2) 0.15257(3) 0.01890(9) Uani 1 1 d . . . O5 O -0.00537(18) -0.28237(14) 0.12820(16) 0.0278(4) Uani 1 1 d . . . O3 O -0.57507(16) -0.45437(13) 0.43620(12) 0.0178(3) Uani 1 1 d . . . O1 O -0.60173(16) -0.70565(13) 0.31341(13) 0.0209(3) Uani 1 1 d . . . O2 O -0.83137(17) -0.80781(15) 0.18112(15) 0.0282(4) Uani 1 1 d . . . C2 C -0.4499(2) -0.61931(18) 0.09768(17) 0.0170(4) Uani 1 1 d . . . H2 H -0.5196 -0.6941 0.0891 0.020 Uiso 1 1 calc R . . N1 N -0.54715(18) -0.51324(15) 0.22784(15) 0.0151(3) Uani 1 1 d . . . O6 O -0.13629(18) -0.17843(14) 0.18411(16) 0.0282(4) Uani 1 1 d . . . C12 C -0.6236(2) -0.39744(18) 0.37122(18) 0.0179(4) Uani 1 1 d . . . C1 C -0.4488(2) -0.50956(17) 0.16461(16) 0.0151(3) Uani 1 1 d . . . C8 C -0.1175(2) -0.27682(18) 0.14782(19) 0.0200(4) Uani 1 1 d . . . C6 C -0.2407(2) -0.50689(19) 0.05907(19) 0.0206(4) Uani 1 1 d . . . H6 H -0.1712 -0.5059 0.0244 0.025 Uiso 1 1 calc R . . C10 C -0.5700(2) -0.39892(18) 0.26976(18) 0.0172(4) Uani 1 1 d . . . H10A H -0.6428 -0.3930 0.2059 0.021 Uiso 1 1 calc R . . H10B H -0.4775 -0.3284 0.2955 0.021 Uiso 1 1 calc R . . O4 O -0.7035(2) -0.34371(19) 0.38718(17) 0.0373(5) Uani 1 1 d . . . C5 C -0.2377(2) -0.39727(18) 0.12627(18) 0.0175(4) Uani 1 1 d . . . C3 C -0.3432(2) -0.39857(18) 0.17679(17) 0.0166(4) Uani 1 1 d . . . H3 H -0.3432 -0.3246 0.2190 0.020 Uiso 1 1 calc R . . C11 C -0.7083(2) -0.71861(18) 0.22629(18) 0.0181(4) Uani 1 1 d . . . C9 C -0.6918(2) -0.61969(18) 0.17046(18) 0.0173(4) Uani 1 1 d . . . H9A H -0.7069 -0.6573 0.0890 0.021 Uiso 1 1 calc R . . H9B H -0.7697 -0.5898 0.1714 0.021 Uiso 1 1 calc R . . C4 C -0.3478(2) -0.61832(18) 0.04356(17) 0.0169(4) Uani 1 1 d . . . C7 C -0.3498(2) -0.73632(18) -0.03041(18) 0.0181(4) Uani 1 1 d . . . O8 O -0.45749(18) -0.83620(14) -0.05692(16) 0.0286(4) Uani 1 1 d . . . N3 N -0.23670(19) -0.38280(16) 0.44995(15) 0.0178(3) Uani 1 1 d . . . O7 O -0.24310(18) -0.72663(14) -0.06323(16) 0.0267(3) Uani 1 1 d . . . N2 N -0.28397(19) -0.61549(16) 0.36012(16) 0.0194(3) Uani 1 1 d . . . O13 O 0.38371(18) 0.00511(14) 0.17263(15) 0.0259(3) Uani 1 1 d D . . O10 O 0.13690(19) -0.00551(14) 0.25177(16) 0.0265(3) Uani 1 1 d D . . O12 O 0.0882(2) -0.11500(18) -0.00092(18) 0.0381(4) Uani 1 1 d D . . C17 C -0.1290(2) -0.40427(19) 0.41644(18) 0.0189(4) Uani 1 1 d . . . C22 C -0.3171(3) -0.7366(2) 0.3153(2) 0.0265(4) Uani 1 1 d . . . H22 H -0.4032 -0.7920 0.3149 0.032 Uiso 1 1 calc R . . O11 O 0.3008(3) -0.15151(18) 0.31127(18) 0.0444(5) Uani 1 1 d D . . C13 C -0.2164(2) -0.2661(2) 0.5021(2) 0.0235(4) Uani 1 1 d . . . H13 H -0.2888 -0.2512 0.5274 0.028 Uiso 1 1 calc R . . C15 C 0.0164(3) -0.1885(2) 0.4828(2) 0.0326(5) Uani 1 1 d . . . H15 H 0.1002 -0.1232 0.4923 0.039 Uiso 1 1 calc R . . C21 C -0.2273(3) -0.7818(2) 0.2695(2) 0.0330(5) Uani 1 1 d . . . H21 H -0.2539 -0.8661 0.2375 0.040 Uiso 1 1 calc R . . C19 C -0.0611(3) -0.5743(2) 0.3210(2) 0.0271(5) Uani 1 1 d . . . H19 H 0.0264 -0.5173 0.3251 0.033 Uiso 1 1 calc R . . C16 C -0.0010(2) -0.3084(2) 0.4315(2) 0.0269(5) Uani 1 1 d . . . H16 H 0.0716 -0.3249 0.4075 0.032 Uiso 1 1 calc R . . C18 C -0.1571(2) -0.53550(19) 0.36359(17) 0.0189(4) Uani 1 1 d . . . C14 C -0.0912(3) -0.1664(2) 0.5198(2) 0.0295(5) Uani 1 1 d . . . H14 H -0.0803 -0.0863 0.5558 0.035 Uiso 1 1 calc R . . C20 C -0.0979(3) -0.6999(2) 0.2720(2) 0.0323(5) Uani 1 1 d . . . H20 H -0.0363 -0.7283 0.2414 0.039 Uiso 1 1 calc R . . O23 O 0.2795(2) 0.08295(17) -0.02684(18) 0.0342(4) Uani 1 1 d D . . O21 O -0.3122(3) -0.0934(2) 0.2923(2) 0.0516(5) Uani 1 1 d D . . O22 O 0.3788(4) 0.0590(4) 0.5094(5) 0.0454(10) Uani 0.50 1 d PD . . O20 O -0.9363(4) -0.5099(4) 0.1313(4) 0.0407(9) Uani 0.50 1 d P . . H22A H 0.389(8) 0.082(6) 0.459(4) 0.049 Uiso 0.50 1 d PD . . H11A H 0.318(4) -0.098(2) 0.373(2) 0.049 Uiso 1 1 d D . . H11B H 0.296(4) -0.212(2) 0.333(3) 0.049 Uiso 1 1 d D . . H10C H 0.142(3) 0.056(2) 0.230(3) 0.049 Uiso 1 1 d D . . H10D H 0.045(2) -0.042(3) 0.229(3) 0.049 Uiso 1 1 d D . . H13A H 0.419(4) -0.030(3) 0.127(3) 0.049 Uiso 1 1 d D . . H13B H 0.368(4) 0.055(3) 0.138(3) 0.049 Uiso 1 1 d D . . H12A H 0.126(3) -0.054(2) -0.021(3) 0.049 Uiso 1 1 d D . . H12B H 0.001(2) -0.138(3) -0.049(3) 0.049 Uiso 1 1 d D . . H23A H 0.235(3) 0.113(3) -0.069(3) 0.049 Uiso 1 1 d D . . H23B H 0.361(2) 0.103(3) -0.037(3) 0.049 Uiso 1 1 d D . . H22B H 0.408(8) 0.108(4) 0.567(3) 0.049 Uiso 0.50 1 d PD . . H21A H -0.392(3) -0.112(3) 0.231(2) 0.049 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01349(13) 0.01587(14) 0.01704(14) 0.00706(10) 0.00864(10) 0.00609(10) Co2 0.01987(15) 0.01286(14) 0.02733(16) 0.00667(11) 0.01466(12) 0.00592(11) O5 0.0264(8) 0.0169(7) 0.0469(10) 0.0096(7) 0.0269(8) 0.0069(6) O3 0.0203(7) 0.0228(7) 0.0190(7) 0.0118(6) 0.0115(6) 0.0127(6) O1 0.0185(7) 0.0178(7) 0.0267(8) 0.0104(6) 0.0080(6) 0.0058(6) O2 0.0205(7) 0.0219(8) 0.0333(9) 0.0132(7) 0.0057(7) -0.0020(6) C2 0.0173(9) 0.0158(9) 0.0190(9) 0.0076(7) 0.0089(7) 0.0047(7) N1 0.0153(7) 0.0136(7) 0.0189(8) 0.0064(6) 0.0104(6) 0.0048(6) O6 0.0279(8) 0.0155(7) 0.0494(10) 0.0121(7) 0.0249(8) 0.0094(6) C12 0.0188(9) 0.0201(9) 0.0207(9) 0.0108(8) 0.0112(8) 0.0092(8) C1 0.0154(8) 0.0173(9) 0.0155(8) 0.0074(7) 0.0086(7) 0.0064(7) C8 0.0236(10) 0.0168(9) 0.0252(10) 0.0101(8) 0.0158(8) 0.0072(8) C6 0.0242(10) 0.0180(9) 0.0245(10) 0.0079(8) 0.0171(8) 0.0072(8) C10 0.0201(9) 0.0173(9) 0.0215(9) 0.0101(7) 0.0131(8) 0.0094(7) O4 0.0566(12) 0.0564(12) 0.0427(10) 0.0361(9) 0.0383(10) 0.0471(10) C5 0.0196(9) 0.0163(9) 0.0207(9) 0.0091(7) 0.0121(8) 0.0064(7) C3 0.0193(9) 0.0152(9) 0.0182(9) 0.0071(7) 0.0101(7) 0.0069(7) C11 0.0188(9) 0.0154(9) 0.0233(10) 0.0073(7) 0.0129(8) 0.0061(7) C9 0.0145(8) 0.0163(9) 0.0208(9) 0.0071(7) 0.0085(7) 0.0037(7) C4 0.0196(9) 0.0168(9) 0.0170(9) 0.0062(7) 0.0100(7) 0.0076(7) C7 0.0187(9) 0.0173(9) 0.0202(9) 0.0066(8) 0.0101(8) 0.0069(7) O8 0.0251(8) 0.0170(7) 0.0417(10) 0.0026(7) 0.0215(7) 0.0034(6) N3 0.0169(8) 0.0196(8) 0.0187(8) 0.0080(7) 0.0083(6) 0.0071(6) O7 0.0278(8) 0.0166(7) 0.0424(10) 0.0080(7) 0.0252(7) 0.0084(6) N2 0.0178(8) 0.0220(8) 0.0212(8) 0.0083(7) 0.0088(7) 0.0095(7) O13 0.0237(8) 0.0167(7) 0.0368(9) 0.0062(7) 0.0158(7) 0.0056(6) O10 0.0293(8) 0.0164(7) 0.0401(9) 0.0099(7) 0.0221(8) 0.0090(6) O12 0.0251(9) 0.0364(10) 0.0416(11) 0.0237(9) 0.0032(8) -0.0018(7) C17 0.0155(9) 0.0228(10) 0.0190(9) 0.0088(8) 0.0074(8) 0.0065(8) C22 0.0244(11) 0.0229(10) 0.0316(12) 0.0075(9) 0.0099(9) 0.0106(9) O11 0.0604(13) 0.0275(9) 0.0386(11) 0.0138(8) 0.0081(10) 0.0164(9) C13 0.0240(10) 0.0233(10) 0.0252(10) 0.0087(8) 0.0117(9) 0.0097(8) C15 0.0237(11) 0.0264(11) 0.0405(14) 0.0124(10) 0.0124(10) -0.0002(9) C21 0.0338(13) 0.0256(11) 0.0387(13) 0.0043(10) 0.0131(11) 0.0166(10) C19 0.0236(10) 0.0355(12) 0.0290(11) 0.0117(10) 0.0158(9) 0.0150(9) C16 0.0182(10) 0.0313(12) 0.0333(12) 0.0134(10) 0.0136(9) 0.0073(9) C18 0.0167(9) 0.0249(10) 0.0169(9) 0.0084(8) 0.0068(7) 0.0093(8) C14 0.0317(12) 0.0200(10) 0.0333(12) 0.0076(9) 0.0130(10) 0.0063(9) C20 0.0308(12) 0.0388(13) 0.0346(13) 0.0087(11) 0.0175(10) 0.0218(11) O23 0.0283(9) 0.0343(9) 0.0492(11) 0.0238(8) 0.0228(8) 0.0099(7) O21 0.0486(13) 0.0494(13) 0.0501(13) 0.0045(10) 0.0120(10) 0.0269(11) O22 0.0255(18) 0.048(2) 0.072(3) 0.016(2) 0.027(2) 0.0221(18) O20 0.0317(19) 0.061(3) 0.042(2) 0.027(2) 0.0174(17) 0.0238(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.0163(15) . ? Co1 O3 2.0787(14) 2_446 ? Co1 N2 2.1068(17) . ? Co1 N3 2.1090(17) . ? Co1 O3 2.1107(14) . ? Co1 N1 2.3177(17) . ? Co2 O7 2.0645(15) 2_545 ? Co2 O12 2.0706(18) . ? Co2 O5 2.0794(15) . ? Co2 O11 2.085(2) . ? Co2 O10 2.0996(16) . ? Co2 O13 2.1357(16) . ? O5 C8 1.253(3) . ? O3 C12 1.288(2) . ? O3 Co1 2.0787(14) 2_446 ? O1 C11 1.256(3) . ? O2 C11 1.251(2) . ? C2 C4 1.394(3) . ? C2 C1 1.395(3) . ? N1 C1 1.443(2) . ? N1 C10 1.477(2) . ? N1 C9 1.480(2) . ? O6 C8 1.267(3) . ? C12 O4 1.218(3) . ? C12 C10 1.527(3) . ? C1 C3 1.393(3) . ? C8 C5 1.506(3) . ? C6 C5 1.387(3) . ? C6 C4 1.390(3) . ? C5 C3 1.393(3) . ? C11 C9 1.527(3) . ? C4 C7 1.506(3) . ? C7 O7 1.251(2) . ? C7 O8 1.263(2) . ? N3 C13 1.340(3) . ? N3 C17 1.353(3) . ? O7 Co2 2.0645(15) 2_545 ? N2 C22 1.343(3) . ? N2 C18 1.347(3) . ? C17 C16 1.393(3) . ? C17 C18 1.479(3) . ? C22 C21 1.386(3) . ? C13 C14 1.390(3) . ? C15 C14 1.377(4) . ? C15 C16 1.383(4) . ? C21 C20 1.380(4) . ? C19 C18 1.385(3) . ? C19 C20 1.391(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 O1 Co1 O3 93.33(6) . 2_446 ? O1 Co1 N2 90.28(7) . . ? O3 Co1 N2 105.99(6) 2_446 . ? O1 Co1 N3 163.57(7) . . ? O3 Co1 N3 100.05(6) 2_446 . ? N2 Co1 N3 76.96(7) . . ? O1 Co1 O3 92.12(6) . . ? O3 Co1 O3 76.44(6) 2_446 . ? N2 Co1 O3 176.49(6) . . ? N3 Co1 O3 100.21(6) . . ? O1 Co1 N1 79.53(6) . . ? O3 Co1 N1 149.60(6) 2_446 . ? N2 Co1 N1 103.58(6) . . ? N3 Co1 N1 93.30(6) . . ? O3 Co1 N1 74.36(5) . . ? O7 Co2 O12 91.40(8) 2_545 . ? O7 Co2 O5 86.99(6) 2_545 . ? O12 Co2 O5 92.77(7) . . ? O7 Co2 O11 90.17(8) 2_545 . ? O12 Co2 O11 175.48(8) . . ? O5 Co2 O11 91.54(8) . . ? O7 Co2 O10 176.94(7) 2_545 . ? O12 Co2 O10 91.65(8) . . ? O5 Co2 O10 92.98(6) . . ? O11 Co2 O10 86.77(8) . . ? O7 Co2 O13 92.39(6) 2_545 . ? O12 Co2 O13 85.84(7) . . ? O5 Co2 O13 178.46(7) . . ? O11 Co2 O13 89.86(8) . . ? O10 Co2 O13 87.72(6) . . ? C8 O5 Co2 129.17(14) . . ? C12 O3 Co1 134.83(13) . 2_446 ? C12 O3 Co1 120.45(12) . . ? Co1 O3 Co1 103.56(6) 2_446 . ? C11 O1 Co1 119.05(13) . . ? C4 C2 C1 120.81(17) . . ? C1 N1 C10 116.47(15) . . ? C1 N1 C9 115.22(15) . . ? C10 N1 C9 109.82(15) . . ? C1 N1 Co1 106.17(11) . . ? C10 N1 Co1 103.40(11) . . ? C9 N1 Co1 104.20(11) . . ? O4 C12 O3 124.87(18) . . ? O4 C12 C10 120.56(18) . . ? O3 C12 C10 114.56(17) . . ? C3 C1 C2 118.74(17) . . ? C3 C1 N1 121.38(17) . . ? C2 C1 N1 119.65(16) . . ? O5 C8 O6 124.98(19) . . ? O5 C8 C5 116.60(18) . . ? O6 C8 C5 118.41(18) . . ? C5 C6 C4 119.91(18) . . ? N1 C10 C12 110.65(15) . . ? C6 C5 C3 120.11(18) . . ? C6 C5 C8 119.97(18) . . ? C3 C5 C8 119.90(18) . . ? C5 C3 C1 120.62(18) . . ? O2 C11 O1 124.47(19) . . ? O2 C11 C9 116.10(18) . . ? O1 C11 C9 119.42(17) . . ? N1 C9 C11 115.07(16) . . ? C6 C4 C2 119.75(18) . . ? C6 C4 C7 119.07(17) . . ? C2 C4 C7 121.17(17) . . ? O7 C7 O8 124.66(19) . . ? O7 C7 C4 116.21(17) . . ? O8 C7 C4 119.12(18) . . ? C13 N3 C17 118.59(18) . . ? C13 N3 Co1 125.77(14) . . ? C17 N3 Co1 115.39(14) . . ? C7 O7 Co2 130.60(14) . 2_545 ? C22 N2 C18 118.73(18) . . ? C22 N2 Co1 124.53(15) . . ? C18 N2 Co1 115.89(14) . . ? N3 C17 C16 121.7(2) . . ? N3 C17 C18 115.40(17) . . ? C16 C17 C18 122.91(19) . . ? N2 C22 C21 122.2(2) . . ? N3 C13 C14 122.5(2) . . ? C14 C15 C16 119.5(2) . . ? C20 C21 C22 119.1(2) . . ? C18 C19 C20 118.9(2) . . ? C15 C16 C17 118.9(2) . . ? N2 C18 C19 122.1(2) . . ? N2 C18 C17 114.71(18) . . ? C19 C18 C17 123.18(19) . . ? C15 C14 C13 118.7(2) . . ? C21 C20 C19 119.0(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.515 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.097 # Attachment 'Compound2.CIF' data_dwni2b _database_code_depnum_ccdc_archive 'CCDC 718746' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 N3 Ni2 O15' _chemical_formula_weight 692.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0968(10) _cell_length_b 12.1101(12) _cell_length_c 12.5860(13) _cell_angle_alpha 103.193(2) _cell_angle_beta 106.046(2) _cell_angle_gamma 107.178(2) _cell_volume 1330.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 207 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.29 _exptl_crystal_description plates _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 1.497 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 14632 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4816 _reflns_number_gt 4357 _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^)+(0.0430P)^2^+0.5865P] 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 4816 _refine_ls_number_parameters 435 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.43490(3) 0.53857(2) 0.10136(2) 0.01234(9) Uani 1 1 d . . . Ni2 Ni 0.18450(3) 0.85961(2) 0.65047(2) 0.01592(9) Uani 1 1 d . . . O1 O 0.60639(15) 0.70232(13) 0.17692(12) 0.0165(3) Uani 1 1 d . . . O2 O 0.83092(17) 0.80898(14) 0.31566(14) 0.0275(4) Uani 1 1 d . . . O3 O 0.57645(15) 0.45516(13) 0.06281(12) 0.0150(3) Uani 1 1 d . . . O4 O 0.71412(19) 0.35022(16) 0.11821(15) 0.0286(4) Uani 1 1 d . . . O5 O 0.23355(18) 0.72726(14) 0.55688(15) 0.0275(4) Uani 1 1 d . . . O8 O 0.13804(17) 0.17927(13) 0.31421(15) 0.0245(4) Uani 1 1 d . . . O6 O 0.45334(18) 0.83412(14) 0.55556(15) 0.0279(4) Uani 1 1 d . . . O11 O 0.37623(17) 1.00128(14) 0.66847(14) 0.0214(3) Uani 1 1 d D . . O10 O 0.3055(2) 0.84381(17) 0.80200(16) 0.0379(4) Uani 1 1 d D . . O12 O 0.0806(2) 0.88999(18) 0.50176(17) 0.0386(5) Uani 1 1 d D . . O7 O -0.00275(17) 0.72012(13) 0.62837(15) 0.0236(4) Uani 1 1 d . . . O13 O 0.13619(18) 0.99042(14) 0.75319(14) 0.0229(3) Uani 1 1 d D . . C1 C 0.4484(2) 0.51085(19) 0.33577(17) 0.0140(4) Uani 1 1 d . . . C2 C 0.4476(2) 0.61957(18) 0.40204(18) 0.0154(4) Uani 1 1 d . . . H2 H 0.5184 0.6944 0.4118 0.019 Uiso 1 1 calc R . . C3 C 0.3434(2) 0.40001(19) 0.32415(18) 0.0158(4) Uani 1 1 d . . . H3 H 0.3459 0.3266 0.2836 0.019 Uiso 1 1 calc R . . C4 C 0.3422(2) 0.61761(19) 0.45390(18) 0.0161(4) Uani 1 1 d . . . C5 C 0.2343(2) 0.39750(19) 0.37264(18) 0.0158(4) Uani 1 1 d . . . C6 C 0.2332(2) 0.50607(19) 0.43699(19) 0.0181(4) Uani 1 1 d . . . H6 H 0.1601 0.5047 0.4688 0.022 Uiso 1 1 calc R . . C7 C 0.3432(2) 0.73564(19) 0.52723(18) 0.0175(4) Uani 1 1 d . . . C8 C 0.1163(2) 0.27640(19) 0.35140(18) 0.0175(4) Uani 1 1 d . . . C9 C 0.6924(2) 0.62115(19) 0.32830(18) 0.0162(4) Uani 1 1 d . . . H9A H 0.7716 0.5909 0.3303 0.019 Uiso 1 1 calc R . . H9B H 0.7052 0.6600 0.4089 0.019 Uiso 1 1 calc R . . C10 C 0.5730(2) 0.40145(19) 0.23133(18) 0.0165(4) Uani 1 1 d . . . H10A H 0.4808 0.3308 0.2058 0.020 Uiso 1 1 calc R . . H10B H 0.6462 0.3955 0.2961 0.020 Uiso 1 1 calc R . . C11 C 0.7099(2) 0.71816(19) 0.26828(18) 0.0171(4) Uani 1 1 d . . . C12 C 0.6288(2) 0.40097(18) 0.13006(18) 0.0156(4) Uani 1 1 d . . . C13 C 0.2236(2) 0.26716(19) -0.00098(19) 0.0205(5) Uani 1 1 d . . . H13 H 0.2969 0.2518 -0.0259 0.025 Uiso 1 1 calc R . . C14 C 0.0976(3) 0.1683(2) -0.0179(2) 0.0265(5) Uani 1 1 d . . . H14 H 0.0872 0.0882 -0.0528 0.032 Uiso 1 1 calc R . . C15 C -0.0115(3) 0.1915(2) 0.0180(2) 0.0288(5) Uani 1 1 d . . . H15 H -0.0966 0.1269 0.0081 0.035 Uiso 1 1 calc R . . C16 C 0.0060(3) 0.3108(2) 0.0685(2) 0.0243(5) Uani 1 1 d . . . H16 H -0.0674 0.3277 0.0922 0.029 Uiso 1 1 calc R . . C17 C 0.1346(2) 0.4056(2) 0.08357(18) 0.0169(4) Uani 1 1 d . . . C18 C 0.1634(2) 0.53698(19) 0.13711(18) 0.0174(4) Uani 1 1 d . . . C19 C 0.0664(3) 0.5769(2) 0.1792(2) 0.0245(5) Uani 1 1 d . . . H19 H -0.0226 0.5208 0.1745 0.029 Uiso 1 1 calc R . . C20 C 0.1047(3) 0.7018(2) 0.2283(2) 0.0287(5) Uani 1 1 d . . . H20 H 0.0423 0.7307 0.2584 0.034 Uiso 1 1 calc R . . C21 C 0.2361(3) 0.7830(2) 0.2322(2) 0.0275(5) Uani 1 1 d . . . H21 H 0.2630 0.8673 0.2641 0.033 Uiso 1 1 calc R . . C22 C 0.3269(3) 0.7370(2) 0.1877(2) 0.0219(5) Uani 1 1 d . . . H22 H 0.4147 0.7917 0.1892 0.026 Uiso 1 1 calc R . . N1 N 0.54735(19) 0.51512(15) 0.27131(15) 0.0137(3) Uani 1 1 d . . . N3 N 0.24330(19) 0.38373(16) 0.04991(15) 0.0158(4) Uani 1 1 d . . . N2 N 0.29303(19) 0.61608(16) 0.14253(15) 0.0158(4) Uani 1 1 d . . . O20 O 0.2804(2) 1.08212(17) 0.47110(17) 0.0322(4) Uani 1 1 d D . . O22 O 0.3234(3) 1.1004(2) 1.2025(2) 0.0513(5) Uani 1 1 d D . . O21 O 0.3710(5) 1.0476(4) 0.9876(5) 0.0515(11) Uani 0.50 1 d P . . O21A O 0.3653(10) 0.9717(11) 1.0276(7) 0.057(3) Uani 0.25 1 d P . . O21B O 0.9390(12) 0.5144(11) 0.3698(10) 0.070(3) Uani 0.25 1 d P . . H13B H 0.043(2) 0.952(3) 0.732(4) 0.085 Uiso 1 1 d D . . H11C H 0.416(4) 0.960(3) 0.629(3) 0.085 Uiso 1 1 d D . . H11D H 0.351(4) 1.046(3) 0.628(3) 0.085 Uiso 1 1 d D . . H12B H 0.129(4) 0.947(3) 0.482(4) 0.085 Uiso 1 1 d D . . H12A H -0.006(3) 0.860(4) 0.446(3) 0.085 Uiso 1 1 d D . . H13A H 0.135(4) 1.045(3) 0.723(3) 0.085 Uiso 1 1 d D . . H22B H 0.253(4) 1.118(4) 1.227(4) 0.085 Uiso 1 1 d D . . H10D H 0.320(5) 0.895(3) 0.867(2) 0.085 Uiso 1 1 d D . . H10C H 0.294(5) 0.781(2) 0.824(3) 0.085 Uiso 1 1 d D . . H22A H 0.410(3) 1.118(4) 1.256(3) 0.085 Uiso 1 1 d D . . H20A H 0.363(2) 1.102(3) 0.459(3) 0.043(8) Uiso 1 1 d D . . H20B H 0.228(3) 1.117(3) 0.435(3) 0.067(12) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01165(15) 0.01364(14) 0.01343(15) 0.00504(11) 0.00677(11) 0.00479(11) Ni2 0.01648(16) 0.01280(15) 0.01994(16) 0.00508(11) 0.01026(12) 0.00464(11) O1 0.0155(7) 0.0156(7) 0.0179(8) 0.0065(6) 0.0067(6) 0.0043(6) O2 0.0196(8) 0.0229(8) 0.0270(9) 0.0120(7) 0.0004(7) -0.0045(7) O3 0.0161(7) 0.0188(7) 0.0151(7) 0.0079(6) 0.0090(6) 0.0088(6) O4 0.0378(10) 0.0424(10) 0.0352(10) 0.0268(8) 0.0280(8) 0.0314(9) O5 0.0255(9) 0.0178(8) 0.0419(10) 0.0046(7) 0.0241(8) 0.0055(7) O8 0.0242(8) 0.0162(8) 0.0405(10) 0.0104(7) 0.0198(8) 0.0097(7) O6 0.0234(9) 0.0171(8) 0.0410(10) 0.0014(7) 0.0210(8) 0.0025(7) O11 0.0193(8) 0.0151(8) 0.0271(9) 0.0041(6) 0.0100(7) 0.0038(6) O10 0.0485(12) 0.0296(10) 0.0320(10) 0.0159(8) 0.0067(9) 0.0136(9) O12 0.0267(10) 0.0383(11) 0.0335(10) 0.0228(9) -0.0022(8) -0.0064(8) O7 0.0223(8) 0.0168(7) 0.0371(9) 0.0080(7) 0.0216(7) 0.0060(7) O13 0.0243(8) 0.0164(8) 0.0311(9) 0.0073(7) 0.0157(7) 0.0073(7) C1 0.0130(10) 0.0195(10) 0.0113(10) 0.0069(8) 0.0056(8) 0.0063(8) C2 0.0150(10) 0.0148(10) 0.0157(10) 0.0067(8) 0.0061(8) 0.0030(8) C3 0.0190(10) 0.0169(10) 0.0155(10) 0.0069(8) 0.0094(9) 0.0083(9) C4 0.0176(10) 0.0176(10) 0.0143(10) 0.0051(8) 0.0076(8) 0.0069(9) C5 0.0160(10) 0.0182(10) 0.0158(10) 0.0084(8) 0.0078(8) 0.0062(9) C6 0.0192(11) 0.0197(11) 0.0188(11) 0.0072(9) 0.0124(9) 0.0064(9) C7 0.0177(11) 0.0167(10) 0.0181(11) 0.0054(9) 0.0081(9) 0.0059(9) C8 0.0200(11) 0.0180(11) 0.0191(11) 0.0090(9) 0.0117(9) 0.0070(9) C9 0.0136(10) 0.0187(10) 0.0172(10) 0.0072(8) 0.0072(8) 0.0050(8) C10 0.0184(11) 0.0179(10) 0.0189(11) 0.0096(9) 0.0108(9) 0.0082(9) C11 0.0176(11) 0.0178(10) 0.0192(11) 0.0065(9) 0.0106(9) 0.0075(9) C12 0.0155(10) 0.0159(10) 0.0187(11) 0.0079(8) 0.0096(9) 0.0057(8) C13 0.0227(11) 0.0210(11) 0.0185(11) 0.0060(9) 0.0102(9) 0.0072(9) C14 0.0302(13) 0.0192(11) 0.0270(12) 0.0068(10) 0.0127(10) 0.0040(10) C15 0.0214(12) 0.0238(12) 0.0316(13) 0.0089(10) 0.0091(10) -0.0032(10) C16 0.0167(11) 0.0312(12) 0.0267(12) 0.0117(10) 0.0114(10) 0.0068(10) C17 0.0143(10) 0.0221(11) 0.0143(10) 0.0072(9) 0.0056(8) 0.0057(9) C18 0.0164(10) 0.0231(11) 0.0146(10) 0.0079(9) 0.0059(8) 0.0089(9) C19 0.0197(11) 0.0325(13) 0.0259(12) 0.0107(10) 0.0125(10) 0.0119(10) C20 0.0264(13) 0.0370(14) 0.0290(13) 0.0076(11) 0.0146(11) 0.0193(11) C21 0.0301(13) 0.0240(12) 0.0278(13) 0.0036(10) 0.0099(10) 0.0144(10) C22 0.0218(11) 0.0201(11) 0.0228(11) 0.0060(9) 0.0067(9) 0.0088(9) N1 0.0134(8) 0.0141(8) 0.0156(9) 0.0059(7) 0.0083(7) 0.0046(7) N3 0.0153(9) 0.0187(9) 0.0144(9) 0.0067(7) 0.0069(7) 0.0056(7) N2 0.0147(9) 0.0188(9) 0.0151(9) 0.0059(7) 0.0064(7) 0.0073(7) O20 0.0243(9) 0.0374(10) 0.0450(11) 0.0255(9) 0.0195(8) 0.0103(8) O22 0.0443(13) 0.0541(13) 0.0551(14) 0.0133(11) 0.0144(11) 0.0259(11) O21 0.036(2) 0.039(2) 0.073(3) 0.004(2) 0.018(2) 0.019(2) O21A 0.041(5) 0.091(7) 0.018(4) -0.009(4) 0.015(4) 0.014(5) O21B 0.076(7) 0.091(8) 0.071(7) 0.040(6) 0.040(6) 0.045(6) _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 2.0089(14) . ? Ni1 N2 2.0455(17) . ? Ni1 O3 2.0578(14) 2_665 ? Ni1 N3 2.0708(17) . ? Ni1 O3 2.0762(14) . ? Ni1 N1 2.2516(17) . ? Ni2 O7 2.0282(15) . ? Ni2 O5 2.0326(15) . ? Ni2 O10 2.0454(18) . ? Ni2 O12 2.0485(18) . ? Ni2 O13 2.0709(16) . ? Ni2 O11 2.0882(16) . ? O1 C11 1.252(3) . ? O2 C11 1.250(3) . ? O3 C12 1.280(2) . ? O3 Ni1 2.0578(14) 2_665 ? O4 C12 1.218(3) . ? O5 C7 1.247(3) . ? O8 C8 1.269(3) . ? O6 C7 1.260(3) . ? O7 C8 1.251(3) 2_566 ? C1 C3 1.389(3) . ? C1 C2 1.392(3) . ? C1 N1 1.448(3) . ? C2 C4 1.391(3) . ? C3 C5 1.396(3) . ? C4 C6 1.394(3) . ? C4 C7 1.510(3) . ? C5 C6 1.383(3) . ? C5 C8 1.502(3) . ? C8 O7 1.251(3) 2_566 ? C9 N1 1.482(3) . ? C9 C11 1.529(3) . ? C10 N1 1.477(3) . ? C10 C12 1.528(3) . ? C13 N3 1.339(3) . ? C13 C14 1.389(3) . ? C14 C15 1.378(4) . ? C15 C16 1.375(3) . ? C16 C17 1.387(3) . ? C17 N3 1.353(3) . ? C17 C18 1.482(3) . ? C18 N2 1.347(3) . ? C18 C19 1.387(3) . ? C19 C20 1.384(3) . ? C20 C21 1.379(4) . ? C21 C22 1.381(3) . ? C22 N2 1.342(3) . ? O21 O21A 1.140(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 O1 Ni1 N2 91.07(6) . . ? O1 Ni1 O3 90.65(6) . 2_665 ? N2 Ni1 O3 105.70(6) . 2_665 ? O1 Ni1 N3 168.29(6) . . ? N2 Ni1 N3 79.12(7) . . ? O3 Ni1 N3 98.11(6) 2_665 . ? O1 Ni1 O3 90.20(6) . . ? N2 Ni1 O3 177.80(6) . . ? O3 Ni1 O3 76.07(6) 2_665 . ? N3 Ni1 O3 99.41(6) . . ? O1 Ni1 N1 81.24(6) . . ? N2 Ni1 N1 102.03(6) . . ? O3 Ni1 N1 151.23(6) 2_665 . ? N3 Ni1 N1 94.46(6) . . ? O3 Ni1 N1 76.40(6) . . ? O7 Ni2 O5 85.58(6) . . ? O7 Ni2 O10 92.78(7) . . ? O5 Ni2 O10 89.24(8) . . ? O7 Ni2 O12 92.65(7) . . ? O5 Ni2 O12 91.74(8) . . ? O10 Ni2 O12 174.54(7) . . ? O7 Ni2 O13 93.21(6) . . ? O5 Ni2 O13 176.85(7) . . ? O10 Ni2 O13 87.91(7) . . ? O12 Ni2 O13 91.22(8) . . ? O7 Ni2 O11 178.47(6) . . ? O5 Ni2 O11 93.36(6) . . ? O10 Ni2 O11 88.31(7) . . ? O12 Ni2 O11 86.27(7) . . ? O13 Ni2 O11 87.90(6) . . ? C11 O1 Ni1 118.14(13) . . ? C12 O3 Ni1 135.84(13) . 2_665 ? C12 O3 Ni1 119.32(12) . . ? Ni1 O3 Ni1 103.93(6) 2_665 . ? C7 O5 Ni2 130.23(14) . . ? C8 O7 Ni2 129.75(14) 2_566 . ? C3 C1 C2 118.71(18) . . ? C3 C1 N1 121.17(18) . . ? C2 C1 N1 119.83(18) . . ? C4 C2 C1 120.74(19) . . ? C1 C3 C5 120.79(19) . . ? C2 C4 C6 119.96(19) . . ? C2 C4 C7 120.60(18) . . ? C6 C4 C7 119.43(18) . . ? C6 C5 C3 120.01(19) . . ? C6 C5 C8 120.58(19) . . ? C3 C5 C8 119.39(19) . . ? C5 C6 C4 119.66(19) . . ? O5 C7 O6 124.7(2) . . ? O5 C7 C4 116.40(18) . . ? O6 C7 C4 118.90(19) . . ? O7 C8 O8 125.09(19) 2_566 . ? O7 C8 C5 116.61(18) 2_566 . ? O8 C8 C5 118.31(18) . . ? N1 C9 C11 114.76(17) . . ? N1 C10 C12 110.56(16) . . ? O2 C11 O1 124.64(19) . . ? O2 C11 C9 115.78(18) . . ? O1 C11 C9 119.57(18) . . ? O4 C12 O3 125.80(19) . . ? O4 C12 C10 119.96(18) . . ? O3 C12 C10 114.24(17) . . ? N3 C13 C14 122.5(2) . . ? C15 C14 C13 118.6(2) . . ? C16 C15 C14 119.6(2) . . ? C15 C16 C17 119.2(2) . . ? N3 C17 C16 121.7(2) . . ? N3 C17 C18 115.28(18) . . ? C16 C17 C18 123.02(19) . . ? N2 C18 C19 122.0(2) . . ? N2 C18 C17 114.61(18) . . ? C19 C18 C17 123.4(2) . . ? C20 C19 C18 118.7(2) . . ? C21 C20 C19 119.5(2) . . ? C20 C21 C22 118.8(2) . . ? N2 C22 C21 122.4(2) . . ? C1 N1 C10 116.27(16) . . ? C1 N1 C9 115.00(16) . . ? C10 N1 C9 109.36(16) . . ? C1 N1 Ni1 107.18(12) . . ? C10 N1 Ni1 102.79(12) . . ? C9 N1 Ni1 104.83(11) . . ? C13 N3 C17 118.50(18) . . ? C13 N3 Ni1 127.01(15) . . ? C17 N3 Ni1 114.13(14) . . ? C22 N2 C18 118.63(18) . . ? C22 N2 Ni1 125.29(15) . . ? C18 N2 Ni1 115.49(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.486 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.076 # Attachment 'Compound3.CIF' data_dwcu3 _database_code_depnum_ccdc_archive 'CCDC 718747' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Cu N3 O8' _chemical_formula_weight 514.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0403(8) _cell_length_b 9.0493(5) _cell_length_c 17.2277(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.9620(10) _cell_angle_gamma 90.00 _cell_volume 2093.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 199 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.25 _exptl_crystal_description plates _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1052 _exptl_absorpt_coefficient_mu 1.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 22967 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3895 _reflns_number_gt 3454 _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^)+(0.0491P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3895 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.095571(15) 0.37562(2) 0.263157(12) 0.01398(9) Uani 1 1 d . . . N3 N 0.18153(11) 0.19537(16) 0.29853(9) 0.0160(3) Uani 1 1 d . . . N2 N 0.05453(11) 0.31998(17) 0.36141(9) 0.0174(3) Uani 1 1 d . . . C22 C 0.24389(14) 0.1386(2) 0.26058(12) 0.0217(4) Uani 1 1 d . . . H22 H 0.2406 0.1721 0.2088 0.026 Uiso 1 1 calc R . . C18 C 0.18475(14) 0.1456(2) 0.37296(11) 0.0187(4) Uani 1 1 d . . . C13 C -0.02260(15) 0.3775(2) 0.38211(12) 0.0232(4) Uani 1 1 d . . . H13 H -0.0600 0.4522 0.3504 0.028 Uiso 1 1 calc R . . C17 C 0.10791(14) 0.2098(2) 0.40632(11) 0.0194(4) Uani 1 1 d . . . C21 C 0.31283(15) 0.0319(2) 0.29600(13) 0.0287(5) Uani 1 1 d . . . H21 H 0.3541 -0.0085 0.2680 0.034 Uiso 1 1 calc R . . C19 C 0.25422(15) 0.0421(2) 0.41294(12) 0.0265(4) Uani 1 1 d . . . H19 H 0.2571 0.0107 0.4650 0.032 Uiso 1 1 calc R . . C14 C -0.04780(17) 0.3285(2) 0.44950(13) 0.0326(5) Uani 1 1 d . . . H14 H -0.1027 0.3678 0.4621 0.039 Uiso 1 1 calc R . . C20 C 0.31946(15) -0.0138(2) 0.37349(14) 0.0325(5) Uani 1 1 d . . . H20 H 0.3677 -0.0821 0.3994 0.039 Uiso 1 1 calc R . . C15 C 0.00906(18) 0.2211(2) 0.49773(13) 0.0352(5) Uani 1 1 d . . . H15 H -0.0055 0.1895 0.5444 0.042 Uiso 1 1 calc R . . C16 C 0.08828(17) 0.1604(2) 0.47614(12) 0.0295(5) Uani 1 1 d . . . H16 H 0.1277 0.0877 0.5081 0.035 Uiso 1 1 calc R . . O2 O 0.04115(9) 0.79437(14) 0.32223(7) 0.0202(3) Uani 1 1 d . . . N1 N 0.24214(10) 0.55464(17) 0.33014(8) 0.0153(3) Uani 1 1 d . . . O5 O 0.48047(11) 0.23662(18) 0.63141(9) 0.0316(4) Uani 1 1 d . . . O8 O 0.54420(10) 0.27287(17) 0.29004(8) 0.0279(3) Uani 1 1 d . . . C2 C 0.33066(13) 0.4455(2) 0.46120(10) 0.0169(4) Uani 1 1 d . . . H2 H 0.2842 0.4862 0.4840 0.020 Uiso 1 1 calc R . . O7 O 0.62516(11) 0.20856(19) 0.41678(9) 0.0357(4) Uani 1 1 d . . . C10 C 0.25371(13) 0.61954(19) 0.25565(11) 0.0164(4) Uani 1 1 d . . . H10B H 0.3239 0.6389 0.2637 0.020 Uiso 1 1 calc R . . H10A H 0.2194 0.7139 0.2467 0.020 Uiso 1 1 calc R . . O6 O 0.35536(11) 0.39170(17) 0.62753(9) 0.0333(4) Uani 1 1 d . . . C3 C 0.39552(13) 0.4129(2) 0.34805(11) 0.0170(4) Uani 1 1 d . . . H3 H 0.3917 0.4288 0.2939 0.020 Uiso 1 1 calc R . . C9 C 0.18172(13) 0.6417(2) 0.36934(11) 0.0188(4) Uani 1 1 d . . . H9A H 0.2154 0.7341 0.3884 0.023 Uiso 1 1 calc R . . H9B H 0.1747 0.5882 0.4161 0.023 Uiso 1 1 calc R . . C11 C 0.07859(13) 0.6744(2) 0.31178(10) 0.0154(4) Uani 1 1 d . . . C8 C 0.55042(14) 0.2678(2) 0.36198(11) 0.0223(4) Uani 1 1 d . . . C4 C 0.40638(14) 0.3580(2) 0.50853(11) 0.0178(4) Uani 1 1 d . . . C5 C 0.47279(13) 0.3295(2) 0.39657(11) 0.0186(4) Uani 1 1 d . . . C1 C 0.32270(12) 0.47381(19) 0.37986(10) 0.0153(4) Uani 1 1 d . . . C6 C 0.47885(14) 0.3002(2) 0.47682(11) 0.0195(4) Uani 1 1 d . . . H6 H 0.5305 0.2430 0.5089 0.023 Uiso 1 1 calc R . . C7 C 0.41001(14) 0.3324(2) 0.59488(11) 0.0219(4) Uani 1 1 d . . . O4 O 0.24257(10) 0.56146(17) 0.11876(8) 0.0286(3) Uani 1 1 d . . . O1 O 0.03752(9) 0.57755(14) 0.26020(8) 0.0175(3) Uani 1 1 d . . . C12 C 0.21473(13) 0.5256(2) 0.17872(11) 0.0174(4) Uani 1 1 d . . . O3 O 0.15516(9) 0.42100(14) 0.17697(7) 0.0182(3) Uani 1 1 d . . . H7 H 0.6657(17) 0.174(2) 0.3996(13) 0.022 Uiso 1 1 d . . . H5 H 0.4847(16) 0.237(2) 0.6758(14) 0.022 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01502(14) 0.01458(14) 0.01361(13) 0.00163(8) 0.00617(9) -0.00006(8) N3 0.0170(8) 0.0140(8) 0.0174(8) 0.0004(6) 0.0056(6) -0.0017(6) N2 0.0204(8) 0.0174(8) 0.0155(8) -0.0005(6) 0.0071(6) -0.0021(6) C22 0.0211(10) 0.0216(10) 0.0248(10) -0.0017(8) 0.0105(8) -0.0015(8) C18 0.0198(10) 0.0160(9) 0.0196(10) -0.0009(7) 0.0047(8) -0.0042(7) C13 0.0252(11) 0.0222(10) 0.0256(11) -0.0007(8) 0.0127(9) 0.0010(8) C17 0.0237(10) 0.0182(9) 0.0157(9) -0.0013(7) 0.0051(8) -0.0044(8) C21 0.0262(11) 0.0235(11) 0.0414(13) 0.0013(9) 0.0177(10) 0.0032(8) C19 0.0279(11) 0.0244(11) 0.0246(10) 0.0077(9) 0.0038(9) 0.0016(8) C14 0.0397(13) 0.0332(12) 0.0348(12) -0.0041(10) 0.0265(11) -0.0005(10) C20 0.0257(11) 0.0254(11) 0.0440(13) 0.0069(10) 0.0061(10) 0.0080(9) C15 0.0526(14) 0.0354(12) 0.0251(11) 0.0028(9) 0.0233(11) -0.0028(11) C16 0.0422(13) 0.0270(11) 0.0209(10) 0.0045(9) 0.0120(9) 0.0005(9) O2 0.0204(7) 0.0216(7) 0.0185(7) -0.0015(5) 0.0055(5) 0.0050(5) N1 0.0136(7) 0.0202(8) 0.0125(7) 0.0016(6) 0.0048(6) 0.0031(6) O5 0.0371(9) 0.0461(9) 0.0117(7) 0.0065(7) 0.0074(7) 0.0184(7) O8 0.0237(7) 0.0478(9) 0.0132(7) -0.0015(6) 0.0068(6) 0.0097(6) C2 0.0145(9) 0.0213(10) 0.0163(9) -0.0025(7) 0.0067(7) 0.0001(7) O7 0.0315(8) 0.0598(11) 0.0185(7) 0.0053(7) 0.0114(7) 0.0306(8) C10 0.0145(9) 0.0181(9) 0.0161(9) 0.0030(7) 0.0037(7) 0.0009(7) O6 0.0341(9) 0.0511(10) 0.0196(7) 0.0059(7) 0.0156(7) 0.0154(7) C3 0.0170(9) 0.0235(9) 0.0102(8) -0.0014(7) 0.0035(7) -0.0002(7) C9 0.0177(9) 0.0209(10) 0.0165(9) -0.0030(7) 0.0029(8) 0.0036(7) C11 0.0168(9) 0.0188(9) 0.0125(9) 0.0035(7) 0.0070(7) 0.0015(7) C8 0.0196(10) 0.0294(11) 0.0171(10) -0.0023(8) 0.0044(8) 0.0049(8) C4 0.0183(9) 0.0219(10) 0.0136(9) -0.0016(7) 0.0052(7) 0.0005(7) C5 0.0174(9) 0.0229(10) 0.0158(9) -0.0019(7) 0.0055(8) 0.0027(8) C1 0.0129(8) 0.0166(9) 0.0152(9) -0.0016(7) 0.0023(7) -0.0020(7) C6 0.0178(9) 0.0243(10) 0.0145(9) 0.0008(7) 0.0016(7) 0.0063(8) C7 0.0202(10) 0.0290(11) 0.0163(9) 0.0006(8) 0.0049(8) 0.0001(8) O4 0.0295(8) 0.0430(9) 0.0161(7) -0.0033(6) 0.0111(6) -0.0200(7) O1 0.0149(6) 0.0173(6) 0.0188(7) 0.0012(5) 0.0027(5) 0.0010(5) C12 0.0137(9) 0.0213(10) 0.0168(9) 0.0020(7) 0.0039(7) -0.0005(7) O3 0.0203(7) 0.0212(7) 0.0148(6) -0.0003(5) 0.0080(5) -0.0050(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 O3 1.9489(12) . ? Cu1 O1 1.9955(13) . ? Cu1 N2 2.0049(15) . ? Cu1 N3 2.0148(15) . ? Cu1 O2 2.1775(12) 2_545 ? N3 C22 1.339(2) . ? N3 C18 1.348(2) . ? N2 C13 1.340(2) . ? N2 C17 1.348(2) . ? C22 C21 1.377(3) . ? C18 C19 1.382(3) . ? C18 C17 1.481(3) . ? C13 C14 1.382(3) . ? C17 C16 1.384(3) . ? C21 C20 1.374(3) . ? C19 C20 1.385(3) . ? C14 C15 1.373(3) . ? C15 C16 1.385(3) . ? O2 C11 1.242(2) . ? O2 Cu1 2.1775(12) 2 ? N1 C1 1.408(2) . ? N1 C9 1.460(2) . ? N1 C10 1.463(2) . ? O5 C7 1.328(2) . ? O8 C8 1.218(2) . ? C2 C4 1.384(3) . ? C2 C1 1.397(2) . ? O7 C8 1.305(2) . ? C10 C12 1.535(2) . ? O6 C7 1.202(2) . ? C3 C5 1.384(3) . ? C3 C1 1.406(2) . ? C9 C11 1.526(2) . ? C11 O1 1.262(2) . ? C8 C5 1.495(3) . ? C4 C6 1.390(3) . ? C4 C7 1.492(2) . ? C5 C6 1.386(3) . ? O4 C12 1.249(2) . ? C12 O3 1.258(2) . ? 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 Cu1 O1 92.90(5) . . ? O3 Cu1 N2 171.55(6) . . ? O1 Cu1 N2 92.04(6) . . ? O3 Cu1 N3 92.78(6) . . ? O1 Cu1 N3 162.41(6) . . ? N2 Cu1 N3 80.55(6) . . ? O3 Cu1 O2 92.65(5) . 2_545 ? O1 Cu1 O2 91.09(5) . 2_545 ? N2 Cu1 O2 94.11(5) . 2_545 ? N3 Cu1 O2 105.26(5) . 2_545 ? C22 N3 C18 119.43(16) . . ? C22 N3 Cu1 125.63(13) . . ? C18 N3 Cu1 114.16(12) . . ? C13 N2 C17 119.47(16) . . ? C13 N2 Cu1 125.49(13) . . ? C17 N2 Cu1 114.95(12) . . ? N3 C22 C21 121.87(18) . . ? N3 C18 C19 121.56(17) . . ? N3 C18 C17 114.34(16) . . ? C19 C18 C17 124.10(17) . . ? N2 C13 C14 121.57(19) . . ? N2 C17 C16 121.29(18) . . ? N2 C17 C18 114.43(16) . . ? C16 C17 C18 124.25(18) . . ? C20 C21 C22 118.73(18) . . ? C18 C19 C20 118.31(19) . . ? C15 C14 C13 119.3(2) . . ? C21 C20 C19 119.98(19) . . ? C14 C15 C16 119.26(19) . . ? C17 C16 C15 119.0(2) . . ? C11 O2 Cu1 121.61(12) . 2 ? C1 N1 C9 118.10(14) . . ? C1 N1 C10 117.85(14) . . ? C9 N1 C10 114.68(14) . . ? C4 C2 C1 121.26(16) . . ? N1 C10 C12 115.61(14) . . ? C5 C3 C1 120.62(16) . . ? N1 C9 C11 111.92(14) . . ? O2 C11 O1 125.70(17) . . ? O2 C11 C9 115.90(16) . . ? O1 C11 C9 118.36(15) . . ? O8 C8 O7 123.76(17) . . ? O8 C8 C5 123.21(17) . . ? O7 C8 C5 113.03(16) . . ? C2 C4 C6 120.54(17) . . ? C2 C4 C7 118.26(16) . . ? C6 C4 C7 121.16(17) . . ? C3 C5 C6 121.06(16) . . ? C3 C5 C8 119.81(16) . . ? C6 C5 C8 119.12(17) . . ? C2 C1 C3 117.70(16) . . ? C2 C1 N1 121.37(15) . . ? C3 C1 N1 120.86(15) . . ? C5 C6 C4 118.77(17) . . ? O6 C7 O5 123.98(18) . . ? O6 C7 C4 123.80(18) . . ? O5 C7 C4 112.22(16) . . ? C11 O1 Cu1 121.26(11) . . ? O4 C12 O3 122.82(17) . . ? O4 C12 C10 116.83(16) . . ? O3 C12 C10 120.31(15) . . ? C12 O3 Cu1 124.80(12) . . ? 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 O7 H7 O4 0.78(2) 1.74(2) 2.5018(19) 165(2) 2_645 O5 H5 O8 0.75(2) 1.90(2) 2.6173(19) 159(2) 4_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.411 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.094