# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- Ni-Zn-Cu-macrocyclic ligands.cif' _publ_contact_author ; Dr. Montserrat Oliv\'an Departamento de Qu\'imica Inorg\'anica - ICMA Universidad de Zaragoza - CSIC 50009 Zaragoza, Spain ; _publ_contact_author_email molivan@unizar.es #-----------------------------------------------------------------------------80 #Publication details loop_ _publ_author_name 'Pellico, D.' "G\'omez-Gallego, M." 'Escudero, R.' "Ram\'irez-L\'opez, P." "Oliv\'an, M." 'Sierra, M. A.' _publ_section_title ; C-Branched Macrocyclic aminoacids: Structure of their Ni(II), Zn(II) and Cu(II) Complexes ; _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? #-----------------------------------------------------------------------------80 # Data for compound 8a-Ni(II) (local labelling data_montse2as) data_montse2as _database_code_depnum_ccdc_archive 'CCDC 819737' #TrackingRef '- Ni-Zn-Cu-macrocyclic ligands.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 N2 Ni O6, 7(H2 O)' _chemical_formula_sum 'C21 H36 N2 Ni O13' _chemical_formula_weight 583.23 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 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 10.5486(10) _cell_length_b 16.1100(15) _cell_length_c 15.8867(15) _cell_angle_alpha 90.00 _cell_angle_beta 108.0310(10) _cell_angle_gamma 90.00 _cell_volume 2567.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3302 _cell_measurement_theta_min 2 _cell_measurement_theta_max 21 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.825 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details ; Absorption correction performed with SADABS program. This is based on the method of Blessing: Blessing, R. H., Acta Crystallogr., Sect. A 1995, 51, 33. SADABS: Area-Detector Absorption Correction. Bruker-AXS within SAINT+ package, v. 6.1 (2000). ; _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 'Bruker SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 27115 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6253 _reflns_number_gt 3550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2008.4-0, Bruker AXS' _computing_cell_refinement 'APEX2 v2008.4-0, Bruker AXS' _computing_data_reduction ; SAINT-Bruker integration program embedded in APEX2 v2008.4-0, Bruker AXS ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, SHELXTL v. 6.1 (Bruker, 2000)' _computing_publication_material 'XCIF, SHELXTL v. 6.1 (Bruker, 2000)' _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^)+(0.0320P)^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 6253 _refine_ls_number_parameters 376 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _refine_ls_shift/su_max 0.014 _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 Ni Ni 0.75814(3) 0.43573(2) 0.50468(2) 0.02041(10) Uani 1 1 d . . . N1 N 0.6285(2) 0.50843(15) 0.41258(15) 0.0223(6) Uani 1 1 d . B . H32 H 0.557(3) 0.5053(18) 0.4168(17) 0.027 Uiso 1 1 d . . . N2 N 0.8735(2) 0.51847(15) 0.59046(15) 0.0204(5) Uani 1 1 d . B . H33 H 0.946(3) 0.5205(17) 0.5885(17) 0.024 Uiso 1 1 d . . . O1 O 0.65933(16) 0.43472(11) 0.59597(11) 0.0236(4) Uani 1 1 d . . . O2 O 0.71840(18) 0.43129(12) 0.74329(12) 0.0273(5) Uani 1 1 d . . . O3 O 0.85019(16) 0.43303(11) 0.40930(11) 0.0235(4) Uani 1 1 d . . . O4 O 0.77816(18) 0.40827(12) 0.26325(12) 0.0275(5) Uani 1 1 d . . . O5 O 0.66216(17) 0.32633(11) 0.43956(12) 0.0248(5) Uani 1 1 d . . . O6 O 0.87476(18) 0.33810(11) 0.58200(12) 0.0259(5) Uani 1 1 d . B . C1 C 0.7616(2) 0.43255(17) 0.33300(18) 0.0212(6) Uani 1 1 d . . . C2 C 0.6218(2) 0.46444(16) 0.32858(17) 0.0214(6) Uani 1 1 d . . . H2 H 0.5910 0.5045 0.2783 0.026 Uiso 1 1 calc R . . C3 C 0.5223(3) 0.39401(17) 0.31365(18) 0.0219(6) Uani 1 1 d . . . C4 C 0.5414(3) 0.32630(17) 0.37107(17) 0.0238(6) Uani 1 1 d . . . C5 C 0.4486(3) 0.26409(18) 0.36038(19) 0.0293(7) Uani 1 1 d . . . H5 H 0.4634 0.2191 0.4009 0.035 Uiso 1 1 calc R . . C6 C 0.3324(3) 0.26845(19) 0.2889(2) 0.0342(8) Uani 1 1 d . . . H6 H 0.2675 0.2257 0.2803 0.041 Uiso 1 1 calc R . . C7 C 0.3106(3) 0.33371(19) 0.2309(2) 0.0343(8) Uani 1 1 d . . . H7 H 0.2309 0.3363 0.1824 0.041 Uiso 1 1 calc R . . C8 C 0.4056(3) 0.39605(19) 0.24346(18) 0.0282(7) Uani 1 1 d . . . H8 H 0.3900 0.4411 0.2029 0.034 Uiso 1 1 calc R . . C9 C 0.6690(3) 0.59736(17) 0.41531(18) 0.0274(7) Uani 1 1 d . . . H9A H 0.5969 0.6307 0.4264 0.033 Uiso 0.50 1 calc PR A 1 H9B H 0.6715 0.6122 0.3554 0.033 Uiso 0.50 1 calc PR A 1 H9C H 0.7498 0.6031 0.3966 0.033 Uiso 0.50 1 calc PR A 2 H9D H 0.5966 0.6308 0.3750 0.033 Uiso 0.50 1 calc PR A 2 C10A C 0.7980(5) 0.6256(3) 0.4800(3) 0.0143(11) Uiso 0.50 1 d P B 1 H10A H 0.8715 0.6017 0.4614 0.017 Uiso 0.50 1 calc PR B 1 H10B H 0.8030 0.6867 0.4749 0.017 Uiso 0.50 1 calc PR B 1 C10B C 0.6962(6) 0.6258(4) 0.5074(4) 0.0377(16) Uiso 0.50 1 d P B 2 H10C H 0.6881 0.6871 0.5057 0.045 Uiso 0.50 1 calc PR B 2 H10D H 0.6237 0.6043 0.5287 0.045 Uiso 0.50 1 calc PR B 2 C11 C 0.8232(3) 0.60519(17) 0.57497(19) 0.0309(7) Uani 1 1 d . . . H11A H 0.7398 0.6107 0.5906 0.037 Uiso 0.50 1 calc PR B 1 H11B H 0.8900 0.6439 0.6124 0.037 Uiso 0.50 1 calc PR B 1 H11C H 0.8171 0.6261 0.6322 0.037 Uiso 0.50 1 calc PR B 2 H11D H 0.8933 0.6383 0.5611 0.037 Uiso 0.50 1 calc PR B 2 C12 C 0.8780(2) 0.48375(17) 0.67866(17) 0.0215(6) Uani 1 1 d . . . H12 H 0.8987 0.5296 0.7232 0.026 Uiso 1 1 calc R B . C13 C 0.7408(3) 0.44705(16) 0.67268(18) 0.0219(6) Uani 1 1 d . B . C14 C 0.9868(2) 0.41891(16) 0.70643(17) 0.0215(6) Uani 1 1 d . B . C15 C 1.0955(3) 0.43028(18) 0.78164(17) 0.0263(7) Uani 1 1 d . . . H15 H 1.0990 0.4782 0.8171 0.032 Uiso 1 1 calc R B . C16 C 1.1991(3) 0.37334(18) 0.80623(19) 0.0313(7) Uani 1 1 d . B . H16 H 1.2721 0.3822 0.8582 0.038 Uiso 1 1 calc R . . C17 C 1.1957(3) 0.30419(19) 0.75518(19) 0.0321(7) Uani 1 1 d . . . H17 H 1.2675 0.2658 0.7713 0.039 Uiso 1 1 calc R B . C18 C 1.0875(3) 0.28998(18) 0.67991(18) 0.0265(7) Uani 1 1 d . B . H18 H 1.0840 0.2415 0.6451 0.032 Uiso 1 1 calc R . . C19 C 0.9857(3) 0.34743(17) 0.65675(17) 0.0232(6) Uani 1 1 d . . . C20 C 0.8486(3) 0.25906(17) 0.53720(19) 0.0285(7) Uani 1 1 d . . . H20A H 0.8802 0.2132 0.5801 0.034 Uiso 1 1 calc R B . H20B H 0.8953 0.2555 0.4920 0.034 Uiso 1 1 calc R . . C21 C 0.7003(3) 0.25324(17) 0.49411(18) 0.0280(7) Uani 1 1 d . B . H21A H 0.6774 0.2024 0.4575 0.034 Uiso 1 1 calc R . . H21B H 0.6539 0.2516 0.5395 0.034 Uiso 1 1 calc R . . O7 O 0.5305(2) 0.33302(15) 0.79089(17) 0.0426(6) Uani 1 1 d D . . H72 H 0.577(3) 0.3642(16) 0.772(2) 0.050 Uiso 1 1 d D . . H71 H 0.564(3) 0.3372(17) 0.8509(18) 0.031(9) Uiso 1 1 d . . . O8 O 0.8401(2) 0.05517(15) 0.51845(15) 0.0457(6) Uani 1 1 d D . . H81 H 0.787(2) 0.0408(18) 0.5450(18) 0.040 Uiso 1 1 d D . . H82 H 0.842(3) 0.0211(15) 0.4808(15) 0.040 Uiso 1 1 d D . . O9 O 0.5390(3) 0.81928(16) 0.29571(17) 0.0515(7) Uani 1 1 d . . . H91 H 0.5172 0.7617 0.2669 0.050 Uiso 1 1 d R . . H92 H 0.583(3) 0.844(2) 0.275(2) 0.048(12) Uiso 1 1 d . . . O10 O 0.8494(2) 0.48906(15) 0.90885(14) 0.0422(6) Uani 1 1 d D . . H101 H 0.826(3) 0.4673(17) 0.8591(10) 0.040 Uiso 1 1 d D . . H102 H 0.868(3) 0.4541(19) 0.942(2) 0.040 Uiso 1 1 d . . . O11 O 0.6115(2) 0.43134(13) 0.09331(13) 0.0432(6) Uani 1 1 d . . . H111 H 0.6608 0.4239 0.1575 0.085(13) Uiso 1 1 d R . . H112 H 0.5220 0.4402 0.0992 0.040 Uiso 1 1 d R . . O12 O 0.8257(3) 0.82665(18) 0.5264(2) 0.0659(8) Uani 1 1 d D . . H121 H 0.854(3) 0.8558(18) 0.4925(18) 0.050 Uiso 1 1 d D . . H122 H 0.7479(15) 0.840(2) 0.520(2) 0.050 Uiso 1 1 d D . . O13 O 0.5242(2) 0.87587(15) 0.45332(16) 0.0433(6) Uani 1 1 d D . . H131 H 0.469(2) 0.9130(14) 0.439(2) 0.040 Uiso 1 1 d D . . H132 H 0.536(3) 0.8560(19) 0.407(2) 0.044(11) 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 Ni 0.01787(18) 0.02062(19) 0.02156(19) -0.00030(17) 0.00439(14) -0.00078(17) N1 0.0181(12) 0.0241(14) 0.0245(13) -0.0020(11) 0.0062(11) -0.0008(11) N2 0.0150(12) 0.0233(13) 0.0232(13) -0.0001(10) 0.0063(10) 0.0006(11) O1 0.0177(9) 0.0301(11) 0.0220(10) -0.0011(9) 0.0045(8) -0.0012(9) O2 0.0275(11) 0.0310(12) 0.0246(10) 0.0009(9) 0.0100(9) -0.0017(10) O3 0.0171(9) 0.0277(11) 0.0249(10) 0.0003(9) 0.0055(8) 0.0002(9) O4 0.0262(11) 0.0342(12) 0.0240(11) -0.0016(9) 0.0105(9) 0.0032(9) O5 0.0235(10) 0.0214(11) 0.0248(10) 0.0018(9) 0.0004(8) -0.0038(9) O6 0.0260(11) 0.0201(11) 0.0257(11) -0.0022(9) -0.0005(9) 0.0027(9) C1 0.0199(14) 0.0180(15) 0.0272(15) 0.0013(13) 0.0095(12) -0.0031(12) C2 0.0201(14) 0.0234(16) 0.0205(14) 0.0021(12) 0.0061(12) 0.0029(12) C3 0.0177(14) 0.0237(16) 0.0244(15) -0.0047(12) 0.0067(12) -0.0001(12) C4 0.0177(14) 0.0289(17) 0.0222(15) -0.0065(13) 0.0025(12) -0.0027(13) C5 0.0284(17) 0.0250(17) 0.0357(18) -0.0042(14) 0.0116(14) -0.0035(13) C6 0.0250(17) 0.036(2) 0.0416(19) -0.0134(16) 0.0094(15) -0.0092(15) C7 0.0204(16) 0.043(2) 0.0364(18) -0.0163(16) 0.0037(14) -0.0016(15) C8 0.0244(16) 0.0331(18) 0.0256(16) -0.0057(13) 0.0056(13) 0.0066(14) C9 0.0336(17) 0.0222(16) 0.0247(16) 0.0029(13) 0.0066(13) -0.0045(13) C11 0.0359(18) 0.0225(17) 0.0305(17) -0.0017(13) 0.0048(14) 0.0078(14) C12 0.0196(14) 0.0234(16) 0.0211(15) -0.0029(12) 0.0054(12) -0.0012(12) C13 0.0208(14) 0.0188(16) 0.0269(15) 0.0006(12) 0.0086(12) 0.0019(12) C14 0.0164(14) 0.0244(17) 0.0236(15) 0.0047(12) 0.0062(12) 0.0000(12) C15 0.0244(15) 0.0273(17) 0.0251(15) 0.0005(13) 0.0048(12) -0.0056(14) C16 0.0204(15) 0.0347(19) 0.0325(17) 0.0083(15) -0.0012(13) -0.0027(14) C17 0.0233(16) 0.0346(19) 0.0358(18) 0.0099(15) 0.0053(14) 0.0046(14) C18 0.0261(16) 0.0248(17) 0.0296(16) 0.0008(13) 0.0102(13) 0.0027(13) C19 0.0173(14) 0.0284(17) 0.0228(15) 0.0043(13) 0.0046(12) -0.0008(12) C20 0.0339(17) 0.0174(16) 0.0318(17) -0.0024(13) 0.0066(14) 0.0038(13) C21 0.0322(17) 0.0198(16) 0.0296(17) 0.0003(13) 0.0062(14) -0.0046(13) O7 0.0333(14) 0.0519(17) 0.0426(15) -0.0017(13) 0.0117(12) -0.0115(11) O8 0.0476(15) 0.0453(16) 0.0440(16) -0.0082(12) 0.0138(12) -0.0033(13) O9 0.0549(17) 0.0506(17) 0.0626(18) -0.0132(14) 0.0381(15) -0.0177(14) O10 0.0442(14) 0.0461(17) 0.0286(14) 0.0032(11) 0.0002(12) 0.0010(12) O11 0.0352(12) 0.0636(16) 0.0304(12) 0.0057(12) 0.0095(10) 0.0070(12) O12 0.073(2) 0.058(2) 0.064(2) 0.0119(15) 0.0150(18) -0.0015(18) O13 0.0454(16) 0.0440(17) 0.0369(15) 0.0008(13) 0.0072(12) 0.0004(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni N2 2.022(2) . ? Ni O1 2.0311(17) . ? Ni N1 2.036(2) . ? Ni O3 2.0376(17) . ? Ni O5 2.1339(18) . ? Ni O6 2.1356(18) . ? N1 C9 1.492(3) . ? N1 C2 1.493(3) . ? N1 H32 0.78(2) . ? N2 C11 1.488(3) . ? N2 C12 1.496(3) . ? N2 H33 0.77(2) . ? O1 C13 1.271(3) . ? O2 C13 1.242(3) . ? O3 C1 1.281(3) . ? O4 C1 1.237(3) . ? O5 C4 1.396(3) . ? O5 C21 1.443(3) . ? O6 C19 1.394(3) . ? O6 C20 1.443(3) . ? C1 C2 1.543(3) . ? C2 C3 1.513(4) . ? C2 H2 1.0000 . ? C3 C8 1.382(4) . ? C3 C4 1.396(4) . ? C4 C5 1.375(4) . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.370(4) . ? C6 H6 0.9500 . ? C7 C8 1.389(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10B 1.474(6) . ? C9 C10A 1.500(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 H9C 0.9900 . ? C9 H9D 0.9900 . ? C10A C11 1.485(5) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C10B C11 1.473(6) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 H11C 0.9900 . ? C11 H11D 0.9900 . ? C12 C14 1.514(3) . ? C12 C13 1.538(3) . ? C12 H12 1.0000 . ? C14 C15 1.388(3) . ? C14 C19 1.394(4) . ? C15 C16 1.387(4) . ? C15 H15 0.9500 . ? C16 C17 1.372(4) . ? C16 H16 0.9500 . ? C17 C18 1.393(4) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C20 C21 1.504(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? O7 H72 0.819(10) . ? O7 H71 0.91(3) . ? O8 H81 0.829(10) . ? O8 H82 0.816(10) . ? O9 H91 1.0282 . ? O9 H92 0.76(3) . ? O10 H101 0.830(10) . ? O10 H102 0.75(3) . ? O11 H111 0.9981 . ? O11 H112 0.9872 . ? O12 H121 0.837(10) . ? O12 H122 0.824(10) . ? O13 H131 0.813(10) . ? O13 H132 0.85(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 N2 Ni O1 81.89(8) . . ? N2 Ni N1 103.63(9) . . ? O1 Ni N1 97.98(8) . . ? N2 Ni O3 100.91(8) . . ? O1 Ni O3 177.19(7) . . ? N1 Ni O3 81.18(8) . . ? N2 Ni O5 165.36(8) . . ? O1 Ni O5 93.91(7) . . ? N1 Ni O5 90.82(8) . . ? O3 Ni O5 83.43(7) . . ? N2 Ni O6 88.77(8) . . ? O1 Ni O6 85.12(7) . . ? N1 Ni O6 167.52(8) . . ? O3 Ni O6 95.15(7) . . ? O5 Ni O6 76.87(7) . . ? C9 N1 C2 114.6(2) . . ? C9 N1 Ni 114.13(16) . . ? C2 N1 Ni 101.82(16) . . ? C9 N1 H32 110(2) . . ? C2 N1 H32 105(2) . . ? Ni N1 H32 111(2) . . ? C11 N2 C12 114.3(2) . . ? C11 N2 Ni 113.46(17) . . ? C12 N2 Ni 102.87(16) . . ? C11 N2 H33 105(2) . . ? C12 N2 H33 108(2) . . ? Ni N2 H33 113(2) . . ? C13 O1 Ni 109.83(16) . . ? C1 O3 Ni 109.15(16) . . ? C4 O5 C21 119.0(2) . . ? C4 O5 Ni 124.04(16) . . ? C21 O5 Ni 112.35(15) . . ? C19 O6 C20 119.8(2) . . ? C19 O6 Ni 126.37(16) . . ? C20 O6 Ni 112.21(15) . . ? O4 C1 O3 125.9(2) . . ? O4 C1 C2 117.5(2) . . ? O3 C1 C2 116.6(2) . . ? N1 C2 C3 109.6(2) . . ? N1 C2 C1 109.7(2) . . ? C3 C2 C1 111.4(2) . . ? N1 C2 H2 108.7 . . ? C3 C2 H2 108.7 . . ? C1 C2 H2 108.7 . . ? C8 C3 C4 117.3(3) . . ? C8 C3 C2 120.7(3) . . ? C4 C3 C2 122.0(2) . . ? C5 C4 C3 122.4(3) . . ? C5 C4 O5 122.7(3) . . ? C3 C4 O5 114.9(2) . . ? C4 C5 C6 118.6(3) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 120.7(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C3 C8 C7 121.4(3) . . ? C3 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10B C9 N1 107.1(3) . . ? C10B C9 C10A 50.8(3) . . ? N1 C9 C10A 120.2(3) . . ? C10B C9 H9A 65.1 . . ? N1 C9 H9A 107.3 . . ? C10A C9 H9A 107.3 . . ? C10B C9 H9B 145.5 . . ? N1 C9 H9B 107.3 . . ? C10A C9 H9B 107.3 . . ? H9A C9 H9B 106.9 . . ? C10B C9 H9C 110.3 . . ? N1 C9 H9C 110.3 . . ? C10A C9 H9C 59.6 . . ? H9A C9 H9C 141.5 . . ? H9B C9 H9C 53.6 . . ? C10B C9 H9D 110.3 . . ? N1 C9 H9D 110.3 . . ? C10A C9 H9D 129.2 . . ? H9A C9 H9D 48.7 . . ? H9B C9 H9D 59.4 . . ? H9C C9 H9D 108.5 . . ? C11 C10A C9 117.9(4) . . ? C11 C10A H10A 107.8 . . ? C9 C10A H10A 107.8 . . ? C11 C10A H10B 107.8 . . ? C9 C10A H10B 107.8 . . ? H10A C10A H10B 107.2 . . ? C11 C10B C9 120.5(5) . . ? C11 C10B H10C 107.2 . . ? C9 C10B H10C 107.2 . . ? C11 C10B H10D 107.2 . . ? C9 C10B H10D 107.2 . . ? H10C C10B H10D 106.8 . . ? C10B C11 C10A 51.1(3) . . ? C10B C11 N2 122.0(3) . . ? C10A C11 N2 108.6(3) . . ? C10B C11 H11A 59.0 . . ? C10A C11 H11A 110.0 . . ? N2 C11 H11A 110.0 . . ? C10B C11 H11B 127.8 . . ? C10A C11 H11B 110.0 . . ? N2 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C10B C11 H11C 106.8 . . ? C10A C11 H11C 144.6 . . ? N2 C11 H11C 106.8 . . ? H11A C11 H11C 54.8 . . ? H11B C11 H11C 58.0 . . ? C10B C11 H11D 106.8 . . ? C10A C11 H11D 64.3 . . ? N2 C11 H11D 106.8 . . ? H11A C11 H11D 142.3 . . ? H11B C11 H11D 49.7 . . ? H11C C11 H11D 106.7 . . ? N2 C12 C14 109.4(2) . . ? N2 C12 C13 109.2(2) . . ? C14 C12 C13 111.5(2) . . ? N2 C12 H12 108.9 . . ? C14 C12 H12 108.9 . . ? C13 C12 H12 108.9 . . ? O2 C13 O1 124.9(2) . . ? O2 C13 C12 117.5(2) . . ? O1 C13 C12 117.6(2) . . ? C15 C14 C19 117.2(3) . . ? C15 C14 C12 120.6(3) . . ? C19 C14 C12 122.2(2) . . ? C16 C15 C14 121.6(3) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C17 C16 C15 119.8(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 118.8(3) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 O6 122.3(3) . . ? C18 C19 C14 122.3(3) . . ? O6 C19 C14 115.4(2) . . ? O6 C20 C21 107.0(2) . . ? O6 C20 H20A 110.3 . . ? C21 C20 H20A 110.3 . . ? O6 C20 H20B 110.3 . . ? C21 C20 H20B 110.3 . . ? H20A C20 H20B 108.6 . . ? O5 C21 C20 106.3(2) . . ? O5 C21 H21A 110.5 . . ? C20 C21 H21A 110.5 . . ? O5 C21 H21B 110.5 . . ? C20 C21 H21B 110.5 . . ? H21A C21 H21B 108.7 . . ? H72 O7 H71 104(3) . . ? H81 O8 H82 111(3) . . ? H91 O9 H92 111.3 . . ? H101 O10 H102 106(3) . . ? H111 O11 H112 97.6 . . ? H121 O12 H122 109(4) . . ? H131 O13 H132 109(3) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.494 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.070 #===END #-----------------------------------------------------------------------------80 # Data for compound 8a-Zn(II) (local labelling montse3as) data_montse3as _database_code_depnum_ccdc_archive 'CCDC 819738' #TrackingRef '- Ni-Zn-Cu-macrocyclic ligands.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 N2 O10 Zn' _chemical_formula_weight 549.87 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.7777(11) _cell_length_b 7.4694(7) _cell_length_c 14.6265(13) _cell_angle_alpha 90.00 _cell_angle_beta 107.0520(10) _cell_angle_gamma 90.00 _cell_volume 1230.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 1.056 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.857 _exptl_absorpt_correction_T_max 0.925 _exptl_absorpt_process_details ; Absorption correction performed with SADABS program. This is based on the method of Blessing: Blessing, R. H., Acta Crystallogr., Sect. A 1995, 51, 33. SADABS: Area-Detector Absorption Correction. Bruker-AXS within SAINT+ package, v. 6.1 (2000). ; _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 'Bruker SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 11233 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.57 _reflns_number_total 5872 _reflns_number_gt 4290 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2008.4-0, Bruker AXS' _computing_cell_refinement 'APEX2 v2008.4-0, Bruker AXS' _computing_data_reduction ; SAINT-Bruker integration program embedded in APEX2 v2008.4-0, Bruker AXS ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, SHELXTL v. 6.1 (Bruker, 2000)' _computing_publication_material 'XCIF, SHELXTL v. 6.1 (Bruker, 2000)' _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^)+(0.0607P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(17) _refine_ls_number_reflns 5872 _refine_ls_number_parameters 328 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 1.681 _refine_ls_shift/su_mean 0.005 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 Zn Zn 0.56404(4) 0.88322(8) 0.14871(3) 0.02404(14) Uani 1 1 d D . . N1 N 0.6167(3) 1.1091(5) 0.0859(3) 0.0222(8) Uani 1 1 d . . . H21 H 0.550(5) 1.132(8) 0.038(4) 0.040 Uiso 1 1 d . . . N2 N 0.6803(4) 0.9288(5) 0.2835(3) 0.0239(9) Uani 1 1 d . . . H22 H 0.752(4) 0.909(8) 0.269(3) 0.038(15) Uiso 1 1 d . . . O1 O 0.5937(3) 0.7679(4) 0.0342(2) 0.0258(7) Uani 1 1 d . . . O2 O 0.6932(3) 0.7931(5) -0.0731(2) 0.0316(8) Uani 1 1 d . . . O3 O 0.5362(3) 0.6521(5) 0.2104(2) 0.0300(8) Uani 1 1 d . . . O4 O 0.5633(3) 0.5182(5) 0.3514(2) 0.0364(9) Uani 1 1 d . . . O5 O 0.8429(3) 0.8274(4) 0.1561(2) 0.0272(8) Uani 1 1 d . . . O6 O 0.8430(3) 0.6470(5) 0.3182(2) 0.0289(8) Uani 1 1 d . . . O7 O 0.3947(3) 0.9628(5) 0.1288(3) 0.0323(8) Uani 1 1 d D . . H71 H 0.373(5) 0.946(8) 0.176(3) 0.050 Uiso 1 1 d D . . H72 H 0.3586(17) 0.961(8) 0.0709(10) 0.050 Uiso 1 1 d D . . C1 C 0.6578(4) 0.8564(8) -0.0069(3) 0.0267(12) Uani 1 1 d . . . C2 C 0.6878(4) 1.0519(7) 0.0224(3) 0.0238(10) Uani 1 1 d . . . H2 H 0.6591 1.1246 -0.0373 0.029 Uiso 1 1 calc R . . C3 C 0.6574(4) 1.2698(7) 0.1465(3) 0.0272(11) Uani 1 1 d . . . H3A H 0.5869 1.3323 0.1547 0.033 Uiso 1 1 calc R . . H3B H 0.6968 1.3522 0.1123 0.033 Uiso 1 1 calc R . . C4 C 0.7425(4) 1.2309(6) 0.2447(3) 0.0259(11) Uani 1 1 d . . . H4A H 0.8124 1.1676 0.2359 0.031 Uiso 1 1 calc R . . H4B H 0.7708 1.3466 0.2761 0.031 Uiso 1 1 calc R . . C5 C 0.6941(5) 1.1207(7) 0.3122(3) 0.0285(11) Uani 1 1 d . . . H5A H 0.7487 1.1305 0.3779 0.034 Uiso 1 1 calc R . . H5B H 0.6161 1.1694 0.3125 0.034 Uiso 1 1 calc R . . C6 C 0.6523(4) 0.8072(6) 0.3531(3) 0.0257(10) Uani 1 1 d . . . H6 H 0.5989 0.8750 0.3828 0.031 Uiso 1 1 calc R . . C7 C 0.5805(4) 0.6453(7) 0.3017(3) 0.0275(11) Uani 1 1 d . . . C8 C 0.8204(4) 1.0843(6) 0.0603(3) 0.0229(10) Uani 1 1 d . . . C9 C 0.8706(4) 1.2334(7) 0.0282(3) 0.0289(11) Uani 1 1 d . . . H9 H 0.8208 1.3140 -0.0160 0.035 Uiso 1 1 calc R . . C10 C 0.9924(4) 1.2647(7) 0.0603(4) 0.0307(11) Uani 1 1 d . . . H10 H 1.0251 1.3662 0.0380 0.037 Uiso 1 1 calc R . . C11 C 1.0664(4) 1.1474(7) 0.1249(4) 0.0328(12) Uani 1 1 d . . . H11 H 1.1496 1.1684 0.1465 0.039 Uiso 1 1 calc R . . C12 C 1.0181(4) 0.9992(7) 0.1579(3) 0.0270(11) Uani 1 1 d . . . H12 H 1.0684 0.9197 0.2025 0.032 Uiso 1 1 calc R . . C13 C 0.8971(4) 0.9672(7) 0.1258(3) 0.0236(10) Uani 1 1 d . . . C14 C 0.9065(5) 0.6628(7) 0.1819(4) 0.0289(11) Uani 1 1 d . . . H14A H 0.9755 0.6621 0.1563 0.035 Uiso 1 1 calc R . . H14B H 0.8541 0.5617 0.1525 0.035 Uiso 1 1 calc R . . C15 C 0.9490(4) 0.6369(8) 0.2880(4) 0.0311(12) Uani 1 1 d . . . H15A H 0.9881 0.5190 0.3043 0.037 Uiso 1 1 calc R . . H15B H 1.0060 0.7320 0.3188 0.037 Uiso 1 1 calc R . . C16 C 0.8548(4) 0.6705(7) 0.4137(3) 0.0267(11) Uani 1 1 d . . . C17 C 0.9536(4) 0.6102(7) 0.4864(4) 0.0334(12) Uani 1 1 d . . . H17 H 1.0192 0.5553 0.4720 0.040 Uiso 1 1 calc R . . C18 C 0.9521(5) 0.6341(8) 0.5822(4) 0.0414(14) Uani 1 1 d . . . H18 H 1.0167 0.5908 0.6329 0.050 Uiso 1 1 calc R . . C19 C 0.8594(5) 0.7181(8) 0.6033(4) 0.0389(14) Uani 1 1 d . . . H19 H 0.8624 0.7376 0.6682 0.047 Uiso 1 1 calc R . . C20 C 0.7605(5) 0.7753(7) 0.5302(3) 0.0324(12) Uani 1 1 d . . . H20 H 0.6954 0.8305 0.5450 0.039 Uiso 1 1 calc R . . C21 C 0.7581(4) 0.7504(7) 0.4337(3) 0.0259(10) Uani 1 1 d . . . O8 O 0.3361(3) 0.3944(9) 0.2641(3) 0.0659(13) Uani 1 1 d . . . O9 O 0.3597(5) 1.0122(8) 0.2984(3) 0.0821(17) Uani 1 1 d . . . O10 O 1.2170(8) 0.7039(12) 0.3092(6) 0.059(2) Uiso 0.50 1 d P . . C22 C 0.5041(14) 1.0662(19) 0.4883(12) 0.083(3) Uiso 0.50 1 d PDU . . C23 C 0.4561(12) 0.884(2) 0.4735(12) 0.094(3) Uiso 0.50 1 d PDU . . O11 O 0.3514(10) 0.8425(17) 0.4687(9) 0.104(3) Uiso 0.50 1 d PDU . . 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 Zn 0.0227(2) 0.0232(3) 0.0233(2) -0.0021(3) 0.00218(18) -0.0026(3) N1 0.020(2) 0.019(2) 0.025(2) -0.0046(17) 0.0028(17) -0.0011(17) N2 0.024(2) 0.022(3) 0.0258(19) -0.0013(15) 0.0064(17) -0.0023(15) O1 0.0220(17) 0.0252(19) 0.0297(18) -0.0075(15) 0.0067(14) -0.0053(15) O2 0.0293(19) 0.035(2) 0.0304(19) -0.0090(16) 0.0091(15) -0.0005(16) O3 0.033(2) 0.027(2) 0.0265(18) -0.0003(16) 0.0039(15) -0.0078(16) O4 0.039(2) 0.036(2) 0.0301(19) 0.0096(17) 0.0046(16) -0.0119(17) O5 0.0199(16) 0.028(2) 0.0323(18) 0.0098(14) 0.0056(14) -0.0004(13) O6 0.0240(18) 0.035(2) 0.0256(17) 0.0001(16) 0.0043(14) 0.0035(15) O7 0.0222(18) 0.038(2) 0.034(2) 0.0082(18) 0.0039(16) 0.0027(15) C1 0.018(2) 0.037(4) 0.021(2) -0.006(2) -0.0005(17) -0.002(2) C2 0.021(2) 0.027(3) 0.020(2) 0.001(2) 0.0016(19) 0.000(2) C3 0.027(3) 0.024(3) 0.031(3) -0.001(2) 0.009(2) -0.001(2) C4 0.028(3) 0.020(3) 0.028(3) -0.003(2) 0.005(2) -0.007(2) C5 0.030(3) 0.025(3) 0.028(3) -0.005(2) 0.004(2) -0.002(2) C6 0.021(2) 0.024(2) 0.029(3) 0.001(2) 0.002(2) 0.0029(19) C7 0.026(3) 0.026(3) 0.030(3) 0.000(2) 0.008(2) -0.005(2) C8 0.021(2) 0.027(3) 0.020(2) -0.005(2) 0.0053(19) -0.002(2) C9 0.030(3) 0.032(3) 0.026(2) 0.001(2) 0.009(2) -0.002(2) C10 0.030(3) 0.029(3) 0.036(3) 0.003(2) 0.015(2) -0.008(2) C11 0.020(2) 0.045(3) 0.033(3) -0.002(2) 0.007(2) -0.012(2) C12 0.020(2) 0.032(3) 0.026(2) -0.001(2) 0.004(2) -0.001(2) C13 0.018(2) 0.032(3) 0.021(2) 0.001(2) 0.0048(19) 0.000(2) C14 0.032(3) 0.023(3) 0.033(3) -0.002(2) 0.009(2) 0.002(2) C15 0.023(3) 0.034(3) 0.037(3) 0.004(2) 0.010(2) 0.007(2) C16 0.028(3) 0.023(3) 0.026(2) 0.003(2) 0.002(2) -0.007(2) C17 0.026(3) 0.030(3) 0.038(3) 0.005(2) -0.001(2) -0.001(2) C18 0.034(3) 0.048(4) 0.031(3) 0.011(3) -0.007(2) -0.011(3) C19 0.052(4) 0.041(3) 0.021(3) 0.002(2) 0.006(2) -0.014(3) C20 0.036(3) 0.034(3) 0.027(3) -0.002(2) 0.008(2) -0.003(2) C21 0.035(3) 0.017(2) 0.023(2) 0.0031(19) 0.003(2) -0.002(2) O8 0.051(2) 0.103(4) 0.043(2) -0.004(3) 0.0124(18) -0.041(3) O9 0.107(4) 0.094(4) 0.061(3) 0.019(3) 0.049(3) 0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn O1 2.003(3) . ? Zn O7 2.018(3) . ? Zn O3 2.018(3) . ? Zn N2 2.072(4) . ? Zn N1 2.100(4) . ? N1 C2 1.484(6) . ? N1 C3 1.485(6) . ? N1 H21 0.90(5) . ? N2 C6 1.472(6) . ? N2 C5 1.490(6) . ? N2 H22 0.95(5) . ? O1 C1 1.279(6) . ? O2 C1 1.254(5) . ? O3 C7 1.285(6) . ? O4 C7 1.248(6) . ? O5 C13 1.365(5) . ? O5 C14 1.431(6) . ? O6 C16 1.374(6) . ? O6 C15 1.444(6) . ? O7 H71 0.820(10) . ? O7 H72 0.828(10) . ? C1 C2 1.533(7) . ? C2 C8 1.515(6) . ? C2 H2 1.0000 . ? C3 C4 1.520(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.518(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C21 1.503(7) . ? C6 C7 1.539(7) . ? C6 H6 1.0000 . ? C8 C9 1.405(7) . ? C8 C13 1.411(6) . ? C9 C10 1.392(7) . ? C9 H9 0.9500 . ? C10 C11 1.392(7) . ? C10 H10 0.9500 . ? C11 C12 1.394(7) . ? C11 H11 0.9500 . ? C12 C13 1.384(6) . ? C12 H12 0.9500 . ? C14 C15 1.497(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.391(7) . ? C16 C17 1.401(7) . ? C17 C18 1.419(7) . ? C17 H17 0.9500 . ? C18 C19 1.371(8) . ? C18 H18 0.9500 . ? C19 C20 1.398(8) . ? C19 H19 0.9500 . ? C20 C21 1.415(6) . ? C20 H20 0.9500 . ? C22 C23 1.466(10) . ? C23 O11 1.253(9) . ? 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 Zn O7 114.39(14) . . ? O1 Zn O3 95.55(14) . . ? O7 Zn O3 91.91(15) . . ? O1 Zn N2 129.61(15) . . ? O7 Zn N2 116.00(16) . . ? O3 Zn N2 82.17(14) . . ? O1 Zn N1 80.41(15) . . ? O7 Zn N1 96.09(15) . . ? O3 Zn N1 171.96(15) . . ? N2 Zn N1 95.00(15) . . ? C2 N1 C3 117.6(4) . . ? C2 N1 Zn 109.6(3) . . ? C3 N1 Zn 118.2(3) . . ? C2 N1 H21 96(3) . . ? C3 N1 H21 111(4) . . ? Zn N1 H21 101(4) . . ? C6 N2 C5 115.3(4) . . ? C6 N2 Zn 109.7(3) . . ? C5 N2 Zn 114.4(3) . . ? C6 N2 H22 118(3) . . ? C5 N2 H22 100(4) . . ? Zn N2 H22 98(3) . . ? C1 O1 Zn 116.3(3) . . ? C7 O3 Zn 115.4(3) . . ? C13 O5 C14 118.9(3) . . ? C16 O6 C15 118.6(4) . . ? Zn O7 H71 112(4) . . ? Zn O7 H72 109.4(11) . . ? H71 O7 H72 132(5) . . ? O2 C1 O1 123.0(5) . . ? O2 C1 C2 118.3(4) . . ? O1 C1 C2 118.7(4) . . ? N1 C2 C8 115.8(4) . . ? N1 C2 C1 108.9(4) . . ? C8 C2 C1 112.5(4) . . ? N1 C2 H2 106.3 . . ? C8 C2 H2 106.3 . . ? C1 C2 H2 106.3 . . ? N1 C3 C4 114.7(4) . . ? N1 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? N1 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 116.7(4) . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? C3 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? N2 C5 C4 111.7(4) . . ? N2 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? N2 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? N2 C6 C21 114.4(4) . . ? N2 C6 C7 110.4(4) . . ? C21 C6 C7 111.8(4) . . ? N2 C6 H6 106.6 . . ? C21 C6 H6 106.6 . . ? C7 C6 H6 106.6 . . ? O4 C7 O3 123.3(5) . . ? O4 C7 C6 118.2(4) . . ? O3 C7 C6 118.3(4) . . ? C9 C8 C13 118.0(4) . . ? C9 C8 C2 119.6(4) . . ? C13 C8 C2 122.4(4) . . ? C10 C9 C8 120.9(5) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 120.1(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 120.2(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? O5 C13 C12 123.7(4) . . ? O5 C13 C8 115.3(4) . . ? C12 C13 C8 121.0(4) . . ? O5 C14 C15 112.0(4) . . ? O5 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? O5 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? O6 C15 C14 104.7(4) . . ? O6 C15 H15A 110.8 . . ? C14 C15 H15A 110.8 . . ? O6 C15 H15B 110.8 . . ? C14 C15 H15B 110.8 . . ? H15A C15 H15B 108.9 . . ? O6 C16 C21 115.0(4) . . ? O6 C16 C17 123.0(5) . . ? C21 C16 C17 121.9(5) . . ? C16 C17 C18 117.4(5) . . ? C16 C17 H17 121.3 . . ? C18 C17 H17 121.3 . . ? C19 C18 C17 121.5(5) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 120.5(5) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C21 119.4(5) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C16 C21 C20 119.2(4) . . ? C16 C21 C6 119.9(4) . . ? C20 C21 C6 120.9(5) . . ? O11 C23 C22 124.6(12) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.165 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.096 #===END #-----------------------------------------------------------------------------80 # Data for compound 8a-Cu(II) (local labelling datat) data_datat _database_code_depnum_ccdc_archive 'CCDC 819739' #TrackingRef '- Ni-Zn-Cu-macrocyclic ligands.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H50 Cu2 N4 O15' _chemical_formula_weight 977.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.4667(13) _cell_length_b 21.127(2) _cell_length_c 16.2489(17) _cell_angle_alpha 90.00 _cell_angle_beta 92.054(2) _cell_angle_gamma 90.00 _cell_volume 4620.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2615 _cell_measurement_theta_min 2 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; Absorption correction performed with SADABS program. This is based on the method of Blessing: Blessing, R. H., Acta Crystallogr., Sect. A 1995, 51, 33. SADABS: Area-Detector Absorption Correction. Bruker-AXS within SAINT+ package, v. 6.1 (2000). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 18880 _diffrn_reflns_av_R_equivalents 0.0919 _diffrn_reflns_av_sigmaI/netI 0.1228 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4511 _reflns_number_gt 2130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2008.4-0, Bruker AXS' _computing_cell_refinement 'APEX2 v2008.4-0, Bruker AXS' _computing_data_reduction ; SAINT-Bruker integration program embedded in APEX2 v2008.4-0, Bruker AXS ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, SHELXTL v. 6.1 (Bruker, 2000)' _computing_publication_material 'XCIF, SHELXTL v. 6.1 (Bruker, 2000)' _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^)+(0.1400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4511 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1579 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.2682 _refine_ls_wR_factor_gt 0.2169 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3936(6) 0.4638(4) 1.1067(4) 0.045(2) Uani 1 1 d . . . C2 C 0.3128(6) 0.4341(4) 1.0522(4) 0.0404(19) Uani 1 1 d . . . H2A H 0.3248 0.3883 1.0520 0.048 Uiso 1 1 calc R . . C3 C 0.2104(6) 0.4445(4) 1.0859(4) 0.044(2) Uani 1 1 d . . . C4 C 0.1498(7) 0.3927(5) 1.1046(5) 0.065(3) Uani 1 1 d . . . H4 H 0.1719 0.3516 1.0958 0.078 Uiso 1 1 calc R . . C5 C 0.0568(8) 0.4030(7) 1.1364(7) 0.086(4) Uani 1 1 d . . . H5 H 0.0175 0.3689 1.1510 0.104 Uiso 1 1 calc R . . C6 C 0.0231(8) 0.4639(7) 1.1461(7) 0.081(3) Uani 1 1 d . . . H6 H -0.0396 0.4707 1.1666 0.097 Uiso 1 1 calc R . . C7 C 0.0809(7) 0.5151(6) 1.1260(6) 0.070(3) Uani 1 1 d . . . H7 H 0.0567 0.5559 1.1322 0.084 Uiso 1 1 calc R . . C8 C 0.1746(6) 0.5058(4) 1.0968(5) 0.046(2) Uani 1 1 d . . . C9 C 0.2237(8) 0.6174(4) 1.1037(6) 0.068(3) Uani 1 1 d . . . H9A H 0.2873 0.6358 1.1205 0.082 Uiso 1 1 calc R . . H9B H 0.1816 0.6177 1.1509 0.082 Uiso 1 1 calc R . . C10 C 0.1768(7) 0.6559(4) 1.0362(6) 0.061(3) Uani 1 1 d . . . H10A H 0.1130 0.6383 1.0188 0.073 Uiso 1 1 calc R . . H10B H 0.1670 0.6992 1.0542 0.073 Uiso 1 1 calc R . . C11 C 0.2203(6) 0.6867(4) 0.9005(6) 0.054(2) Uani 1 1 d . . . C12 C 0.1404(7) 0.7259(5) 0.8895(7) 0.073(3) Uani 1 1 d . . . H12 H 0.0960 0.7320 0.9314 0.088 Uiso 1 1 calc R . . C13 C 0.1268(9) 0.7568(5) 0.8137(8) 0.088(4) Uani 1 1 d . . . H13 H 0.0710 0.7822 0.8049 0.105 Uiso 1 1 calc R . . C14 C 0.1913(11) 0.7510(6) 0.7537(8) 0.100(4) Uani 1 1 d . . . H14 H 0.1819 0.7736 0.7049 0.120 Uiso 1 1 calc R . . C15 C 0.2711(8) 0.7118(5) 0.7646(6) 0.075(3) Uani 1 1 d . . . H15 H 0.3151 0.7069 0.7222 0.090 Uiso 1 1 calc R . . C16 C 0.2880(6) 0.6790(4) 0.8377(5) 0.050(2) Uani 1 1 d . . . C17 C 0.3787(6) 0.6362(4) 0.8482(5) 0.045(2) Uani 1 1 d . . . H17 H 0.4170 0.6411 0.7984 0.054 Uiso 1 1 calc R . . C18 C 0.4465(6) 0.6587(4) 0.9211(5) 0.049(2) Uani 1 1 d . . . C19 C 0.2592(6) 0.5480(4) 0.8219(4) 0.044(2) Uani 1 1 d . . . H19A H 0.2512 0.5618 0.7651 0.053 Uiso 1 1 calc R . . H19B H 0.2071 0.5673 0.8530 0.053 Uiso 1 1 calc R . . C20 C 0.2499(7) 0.4756(4) 0.8260(5) 0.053(2) Uani 1 1 d . . . H20A H 0.1954 0.4624 0.7894 0.063 Uiso 1 1 calc R . . H20B H 0.3103 0.4569 0.8062 0.063 Uiso 1 1 calc R . . C21 C 0.2322(7) 0.4502(4) 0.9123(5) 0.054(2) Uani 1 1 d . . . H21A H 0.1778 0.4732 0.9360 0.065 Uiso 1 1 calc R . . H21B H 0.2137 0.4059 0.9088 0.065 Uiso 1 1 calc R . . Cu1 Cu 0.39063(7) 0.53971(5) 0.97028(5) 0.0397(4) Uani 1 1 d . . . N2 N 0.3222(5) 0.4571(3) 0.9659(3) 0.0398(15) Uani 1 1 d . . . H2 H 0.3817 0.4318 0.9401 0.048 Uiso 1 1 d R . . N1 N 0.3563(5) 0.5683(3) 0.8555(3) 0.0381(15) Uani 1 1 d . . . H1 H 0.4067 0.5451 0.8199 0.046 Uiso 1 1 d R . . O1 O 0.2382(5) 0.5528(3) 1.0766(4) 0.0599(17) Uani 1 1 d . . . O2 O 0.2443(4) 0.6538(3) 0.9708(3) 0.0592(16) Uani 1 1 d . . . O3 O 0.4422(4) 0.5103(3) 1.0770(3) 0.0456(14) Uani 1 1 d . . . O4 O 0.4616(4) 0.6183(3) 0.9802(3) 0.0485(14) Uani 1 1 d . . . O5 O 0.4111(4) 0.4417(3) 1.1767(3) 0.0628(18) Uani 1 1 d . . . O6 O 0.4832(5) 0.7117(3) 0.9206(4) 0.074(2) Uani 1 1 d . . . O7 O 0.4313(9) 0.3573(5) 0.8747(7) 0.057(3) Uiso 0.50 1 d P . . H71 H 0.4057 0.3260 0.9080 0.068 Uiso 0.50 1 d PR . . H72 H 0.5048 0.3622 0.8956 0.068 Uiso 0.50 1 d PR . . O8 O 0.5000 0.4294(8) 0.7500 0.060(4) Uiso 0.50 2 d SP . . O9 O 0.6519(19) 0.7306(12) 1.0250(14) 0.068(7) Uiso 0.25 1 d P . . O10 O 0.5215(11) 0.8254(7) 0.8389(9) 0.088(4) Uiso 0.50 1 d P . . H100 H 0.5650 0.8191 0.8681 0.106 Uiso 0.50 1 d PR . . H101 H 0.5477 0.8473 0.8066 0.106 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(4) 0.073(6) 0.031(4) 0.003(4) 0.004(3) 0.012(4) C2 0.041(5) 0.047(5) 0.033(4) 0.001(3) 0.006(3) 0.000(4) C3 0.030(5) 0.067(6) 0.033(4) 0.004(4) -0.001(3) -0.006(4) C4 0.061(7) 0.081(7) 0.053(5) 0.005(5) 0.005(5) -0.019(6) C5 0.055(8) 0.125(11) 0.080(7) 0.024(7) 0.008(6) -0.044(7) C6 0.038(6) 0.131(11) 0.074(7) 0.003(7) 0.011(5) -0.004(7) C7 0.041(6) 0.112(9) 0.056(6) -0.009(6) 0.008(5) 0.007(6) C8 0.028(5) 0.072(6) 0.038(4) 0.000(4) 0.004(3) 0.005(4) C9 0.078(7) 0.066(7) 0.063(6) -0.020(5) 0.024(5) -0.004(6) C10 0.056(6) 0.055(6) 0.073(6) -0.006(5) 0.026(5) 0.012(5) C11 0.044(5) 0.050(5) 0.066(6) -0.004(4) -0.008(4) 0.012(4) C12 0.055(6) 0.060(6) 0.104(8) -0.026(6) -0.020(6) 0.018(5) C13 0.092(9) 0.059(7) 0.110(10) -0.010(7) -0.037(8) 0.029(6) C14 0.138(12) 0.081(9) 0.077(8) 0.020(7) -0.029(8) 0.038(9) C15 0.090(8) 0.070(7) 0.062(6) 0.015(5) -0.024(5) 0.014(6) C16 0.048(5) 0.051(5) 0.051(5) 0.003(4) -0.011(4) 0.004(4) C17 0.045(5) 0.054(5) 0.037(4) 0.009(4) 0.008(4) 0.009(4) C18 0.042(5) 0.053(6) 0.053(5) 0.000(4) 0.004(4) -0.005(4) C19 0.037(5) 0.063(6) 0.033(4) 0.000(4) -0.002(3) 0.002(4) C20 0.061(6) 0.063(6) 0.033(4) -0.007(4) -0.003(4) -0.001(5) C21 0.062(6) 0.061(6) 0.040(4) 0.004(4) 0.001(4) -0.016(5) Cu1 0.0346(6) 0.0537(7) 0.0305(5) 0.0018(4) -0.0025(4) 0.0025(5) N2 0.038(4) 0.055(4) 0.026(3) 0.003(3) 0.003(3) 0.007(3) N1 0.036(4) 0.043(4) 0.036(3) -0.004(3) 0.004(3) 0.005(3) O1 0.055(4) 0.055(4) 0.072(4) 0.001(3) 0.023(3) 0.007(3) O2 0.050(4) 0.072(4) 0.057(4) 0.000(3) 0.014(3) 0.017(3) O3 0.032(3) 0.069(4) 0.036(3) 0.005(3) -0.003(2) -0.003(3) O4 0.042(3) 0.061(4) 0.042(3) 0.000(3) -0.005(2) -0.003(3) O5 0.044(4) 0.111(5) 0.033(3) 0.022(3) 0.000(2) 0.007(3) O6 0.071(5) 0.067(5) 0.084(5) 0.011(4) -0.017(4) -0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O5 1.245(9) . ? C1 O3 1.284(9) . ? C1 C2 1.514(11) . ? C1 Cu1 2.735(8) . ? C2 N2 1.495(9) . ? C2 C3 1.517(11) . ? C2 H2A 0.9800 . ? C3 C8 1.395(12) . ? C3 C4 1.404(12) . ? C4 C5 1.389(14) . ? C4 H4 0.9300 . ? C5 C6 1.375(15) . ? C5 H5 0.9300 . ? C6 C7 1.378(14) . ? C6 H6 0.9300 . ? C7 C8 1.378(12) . ? C7 H7 0.9300 . ? C8 O1 1.359(10) . ? C9 O1 1.450(10) . ? C9 C10 1.488(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O2 1.424(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.364(12) . ? C11 O2 1.366(10) . ? C11 C16 1.402(12) . ? C12 C13 1.400(15) . ? C12 H12 0.9300 . ? C13 C14 1.334(16) . ? C13 H13 0.9300 . ? C14 C15 1.364(14) . ? C14 H14 0.9300 . ? C15 C16 1.386(11) . ? C15 H15 0.9300 . ? C16 C17 1.526(11) . ? C17 N1 1.471(10) . ? C17 C18 1.544(11) . ? C17 H17 0.9800 . ? C18 O6 1.224(10) . ? C18 O4 1.296(9) . ? C18 Cu1 2.751(9) . ? C19 N1 1.464(9) . ? C19 C20 1.535(10) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.528(11) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N2 1.474(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? Cu1 O4 1.919(6) . ? Cu1 O3 1.947(5) . ? Cu1 N2 1.974(6) . ? Cu1 N1 1.998(6) . ? Cu1 O3 2.627(5) 5_667 ? Cu1 Cu1 3.4959(18) 5_667 ? N2 H2 1.0609 . ? N1 H1 1.0321 . ? O3 Cu1 2.627(5) 5_667 ? O7 H71 0.9293 . ? O7 H72 1.0390 . ? O10 H100 0.7525 . ? O10 H101 0.7931 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 C1 O3 123.3(7) . . ? O5 C1 C2 119.1(8) . . ? O3 C1 C2 117.6(6) . . ? O5 C1 Cu1 163.3(7) . . ? O3 C1 Cu1 40.5(3) . . ? C2 C1 Cu1 77.3(4) . . ? N2 C2 C1 109.3(6) . . ? N2 C2 C3 113.6(6) . . ? C1 C2 C3 111.9(6) . . ? N2 C2 H2A 107.3 . . ? C1 C2 H2A 107.3 . . ? C3 C2 H2A 107.3 . . ? C8 C3 C4 119.3(8) . . ? C8 C3 C2 120.2(7) . . ? C4 C3 C2 120.5(8) . . ? C5 C4 C3 119.8(10) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 119.7(10) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 121.0(10) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C8 120.1(11) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? O1 C8 C7 124.9(9) . . ? O1 C8 C3 115.1(7) . . ? C7 C8 C3 120.1(9) . . ? O1 C9 C10 110.4(8) . . ? O1 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? O1 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O2 C10 C9 105.6(7) . . ? O2 C10 H10A 110.6 . . ? C9 C10 H10A 110.6 . . ? O2 C10 H10B 110.6 . . ? C9 C10 H10B 110.6 . . ? H10A C10 H10B 108.8 . . ? C12 C11 O2 125.5(9) . . ? C12 C11 C16 120.4(9) . . ? O2 C11 C16 114.1(7) . . ? C11 C12 C13 118.3(10) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C14 C13 C12 122.2(10) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 119.4(11) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 121.2(11) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C11 118.4(8) . . ? C15 C16 C17 119.9(8) . . ? C11 C16 C17 121.8(7) . . ? N1 C17 C16 114.9(7) . . ? N1 C17 C18 110.8(6) . . ? C16 C17 C18 110.6(7) . . ? N1 C17 H17 106.6 . . ? C16 C17 H17 106.6 . . ? C18 C17 H17 106.6 . . ? O6 C18 O4 123.7(8) . . ? O6 C18 C17 120.3(8) . . ? O4 C18 C17 116.0(7) . . ? O6 C18 Cu1 162.2(6) . . ? O4 C18 Cu1 38.7(4) . . ? C17 C18 Cu1 77.3(5) . . ? N1 C19 C20 110.4(6) . . ? N1 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N1 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C19 113.9(6) . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20B 108.8 . . ? C19 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? N2 C21 C20 110.8(7) . . ? N2 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? O4 Cu1 O3 92.3(2) . . ? O4 Cu1 N2 176.6(2) . . ? O3 Cu1 N2 84.3(2) . . ? O4 Cu1 N1 85.1(2) . . ? O3 Cu1 N1 172.3(2) . . ? N2 Cu1 N1 98.1(2) . . ? O4 Cu1 O3 86.7(2) . 5_667 ? O3 Cu1 O3 81.4(2) . 5_667 ? N2 Cu1 O3 92.1(2) . 5_667 ? N1 Cu1 O3 91.2(2) . 5_667 ? O4 Cu1 C1 116.5(2) . . ? O3 Cu1 C1 25.4(2) . . ? N2 Cu1 C1 60.3(2) . . ? N1 Cu1 C1 158.4(3) . . ? O3 Cu1 C1 90.8(2) 5_667 . ? O4 Cu1 C18 25.0(2) . . ? O3 Cu1 C18 117.3(2) . . ? N2 Cu1 C18 158.4(2) . . ? N1 Cu1 C18 60.6(2) . . ? O3 Cu1 C18 92.1(2) 5_667 . ? C1 Cu1 C18 140.8(3) . . ? O4 Cu1 Cu1 88.84(16) . 5_667 ? O3 Cu1 Cu1 47.98(16) . 5_667 ? N2 Cu1 Cu1 88.45(18) . 5_667 ? N1 Cu1 Cu1 124.56(18) . 5_667 ? O3 Cu1 Cu1 33.40(11) 5_667 5_667 ? C1 Cu1 Cu1 60.45(16) . 5_667 ? C18 Cu1 Cu1 106.40(18) . 5_667 ? C21 N2 C2 115.3(6) . . ? C21 N2 Cu1 118.8(5) . . ? C2 N2 Cu1 108.0(4) . . ? C21 N2 H2 109.5 . . ? C2 N2 H2 107.3 . . ? Cu1 N2 H2 95.8 . . ? C19 N1 C17 116.0(6) . . ? C19 N1 Cu1 115.7(5) . . ? C17 N1 Cu1 109.2(4) . . ? C19 N1 H1 104.3 . . ? C17 N1 H1 106.1 . . ? Cu1 N1 H1 104.2 . . ? C8 O1 C9 121.5(7) . . ? C11 O2 C10 118.0(7) . . ? C1 O3 Cu1 114.1(4) . . ? C1 O3 Cu1 104.8(5) . 5_667 ? Cu1 O3 Cu1 98.6(2) . 5_667 ? C18 O4 Cu1 116.3(5) . . ? H71 O7 H72 104.5 . . ? H100 O10 H101 99.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O5 1.03 2.47 3.201(8) 127.3 5_667 N1 H1 O5 1.03 2.35 3.031(8) 122.7 6_565 N2 H2 O7 1.06 2.03 2.992(13) 149.9 . N2 H2 O4 1.06 2.66 3.405(8) 127.3 5_667 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.567 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.136 #===END