# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Leonard Lindoy' 'Jack K Clegg' 'Michael J Hayter' 'Katrina A Jolliffe' 'John C McMurtrie' 'George Meehan' 'Suzanne M. Neville' 'Simon Parsons' 'Peter Tasker' 'Peter Turner' 'Fraser White' _publ_contact_author_name 'Leonard Lindoy' _publ_contact_author_email LINDOY@GMAIL.COM _publ_section_title ; New discrete and polymeric supramolecular architectures derived from dinuclear Co(II), Ni(II) and Cu(II) complexes of aryl-linked bis-beta-diketonato ligands and nitrogen bases: synthetic, structural and high pressure studies ; # Attachment 'Cu_mmorph_150K.CIF' data_lj151sad _database_code_depnum_ccdc_archive 'CCDC 754701' #TrackingRef 'Cu_mmorph_150K.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H70 Cu2 N2 O10' _chemical_formula_sum 'C50 H70 Cu2 N2 O10' _chemical_formula_weight 986.16 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 triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' #_intl_tables_symmetry_no. '2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9932(5) _cell_length_b 11.2678(9) _cell_length_c 16.4656(14) _cell_angle_alpha 83.877(7) _cell_angle_beta 84.620(5) _cell_angle_gamma 73.405(6) _cell_volume 1233.59(17) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1900 _cell_measurement_theta_min 3.002 _cell_measurement_theta_max 23.99 _exptl_crystal_description blade _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29756 _diffrn_reflns_av_R_equivalents 0.0709 _diffrn_reflns_av_sigmaI/netI 0.0744 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6109 _reflns_number_gt 4236 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0518P)^2^+0.0759P] 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 6109 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0862(4) 0.3284(3) 0.4464(2) 0.0457(8) Uani 1 1 d . . . H1A H 0.0079 0.4143 0.4330 0.069 Uiso 1 1 calc R . . H1B H 0.0761 0.3086 0.5058 0.069 Uiso 1 1 calc R . . H1C H 0.0343 0.2719 0.4192 0.069 Uiso 1 1 calc R . . C2 C 0.3893(5) 0.3991(3) 0.4612(2) 0.0461(8) Uani 1 1 d . . . H2A H 0.5293 0.3904 0.4421 0.069 Uiso 1 1 calc R . . H2B H 0.3807 0.3765 0.5203 0.069 Uiso 1 1 calc R . . H2C H 0.3104 0.4854 0.4496 0.069 Uiso 1 1 calc R . . C3 C 0.4284(5) 0.1789(3) 0.43694(19) 0.0427(8) Uani 1 1 d . . . H3A H 0.3781 0.1233 0.4082 0.064 Uiso 1 1 calc R . . H3B H 0.4156 0.1577 0.4961 0.064 Uiso 1 1 calc R . . H3C H 0.5694 0.1696 0.4194 0.064 Uiso 1 1 calc R . . C4 C 0.3073(4) 0.3131(2) 0.41679(17) 0.0260(6) Uani 1 1 d . . . C5 C 0.3131(3) 0.3565(2) 0.32551(16) 0.0189(5) Uani 1 1 d . . . C6 C 0.4076(3) 0.2747(2) 0.26545(16) 0.0203(5) Uani 1 1 d . . . H6 H 0.4681 0.1904 0.2834 0.024 Uiso 1 1 calc R . . C7 C 0.4184(3) 0.3088(2) 0.18161(16) 0.0187(5) Uani 1 1 d . . . C8 C 0.5213(3) 0.2133(2) 0.12311(16) 0.0183(5) Uani 1 1 d . . . C9 C 0.5805(3) 0.2527(2) 0.04399(16) 0.0195(5) Uani 1 1 d . . . H9 H 0.5535 0.3393 0.0285 0.023 Uiso 1 1 calc R . . C10 C 0.6787(3) 0.1682(2) -0.01324(16) 0.0194(5) Uani 1 1 d . . . C11 C 0.7199(4) 0.0407(2) 0.01087(17) 0.0264(6) Uani 1 1 d . . . H11 H 0.7897 -0.0184 -0.0263 0.032 Uiso 1 1 calc R . . C12 C 0.6585(4) 0.0013(2) 0.08885(17) 0.0298(6) Uani 1 1 d . . . H12 H 0.6848 -0.0852 0.1044 0.036 Uiso 1 1 calc R . . C13 C 0.5594(4) 0.0855(2) 0.14474(17) 0.0239(6) Uani 1 1 d . . . H13 H 0.5173 0.0565 0.1978 0.029 Uiso 1 1 calc R . . C14 C 0.7311(3) 0.2182(2) -0.09800(16) 0.0198(5) Uani 1 1 d . . . C15 C 0.8121(4) 0.1379(2) -0.15955(17) 0.0248(6) Uani 1 1 d . . . H15 H 0.8329 0.0514 -0.1456 0.030 Uiso 1 1 calc R . . C16 C 0.8649(3) 0.1763(2) -0.24027(16) 0.0219(6) Uani 1 1 d . . . C17 C 0.9418(4) 0.0843(2) -0.30627(17) 0.0253(6) Uani 1 1 d . . . C18 C 1.1451(4) 0.1006(3) -0.34345(18) 0.0327(7) Uani 1 1 d . . . H18A H 1.1929 0.0478 -0.3889 0.049 Uiso 1 1 calc R . . H18B H 1.2425 0.0767 -0.3014 0.049 Uiso 1 1 calc R . . H18C H 1.1287 0.1878 -0.3636 0.049 Uiso 1 1 calc R . . C19 C 0.9737(4) -0.0528(2) -0.27362(19) 0.0333(7) Uani 1 1 d . . . H19A H 0.8456 -0.0658 -0.2514 0.050 Uiso 1 1 calc R . . H19B H 1.0679 -0.0736 -0.2303 0.050 Uiso 1 1 calc R . . H19C H 1.0280 -0.1062 -0.3183 0.050 Uiso 1 1 calc R . . C20 C 0.7904(5) 0.1191(3) -0.3723(2) 0.0419(8) Uani 1 1 d . . . H20A H 0.6625 0.1070 -0.3489 0.063 Uiso 1 1 calc R . . H20B H 0.8407 0.0662 -0.4176 0.063 Uiso 1 1 calc R . . H20C H 0.7711 0.2064 -0.3927 0.063 Uiso 1 1 calc R . . C21 C -0.2864(4) 0.5950(3) 0.2873(2) 0.0410(8) Uani 1 1 d . . . H21A H -0.1630 0.5782 0.3167 0.049 Uiso 1 1 calc R . . H21B H -0.3970 0.6490 0.3199 0.049 Uiso 1 1 calc R . . C22 C -0.2591(4) 0.6607(3) 0.20536(19) 0.0333(7) Uani 1 1 d . . . H22A H -0.3851 0.6817 0.1773 0.040 Uiso 1 1 calc R . . H22B H -0.2284 0.7393 0.2125 0.040 Uiso 1 1 calc R . . C23 C -0.1405(4) 0.4626(2) 0.14931(19) 0.0330(7) Uani 1 1 d . . . H23A H -0.0278 0.4064 0.1190 0.040 Uiso 1 1 calc R . . H23B H -0.2622 0.4766 0.1192 0.040 Uiso 1 1 calc R . . C24 C -0.1717(4) 0.4032(3) 0.2343(2) 0.0404(8) Uani 1 1 d . . . H24A H -0.2004 0.3231 0.2301 0.048 Uiso 1 1 calc R . . H24B H -0.0473 0.3858 0.2631 0.048 Uiso 1 1 calc R . . C25 C -0.0905(4) 0.6428(3) 0.07130(19) 0.0393(7) Uani 1 1 d . . . H25A H -0.2165 0.6507 0.0469 0.059 Uiso 1 1 calc R . . H25B H 0.0208 0.5918 0.0384 0.059 Uiso 1 1 calc R . . H25C H -0.0717 0.7254 0.0727 0.059 Uiso 1 1 calc R . . N1 N -0.0965(3) 0.5840(2) 0.15431(14) 0.0278(5) Uani 1 1 d . . . O1 O 0.2232(2) 0.47060(15) 0.30918(11) 0.0224(4) Uani 1 1 d . . . O2 O 0.3509(2) 0.41918(15) 0.14774(11) 0.0209(4) Uani 1 1 d . . . O3 O 0.6928(2) 0.33676(15) -0.10850(11) 0.0222(4) Uani 1 1 d . . . O4 O 0.8515(3) 0.28902(16) -0.26653(11) 0.0263(4) Uani 1 1 d . . . O5 O -0.3305(3) 0.4801(2) 0.28015(14) 0.0464(6) Uani 1 1 d . . . Cu1 Cu 0.23595(4) 0.56594(3) 0.20533(2) 0.02157(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0432(17) 0.056(2) 0.030(2) 0.0084(16) 0.0111(14) -0.0107(16) C2 0.070(2) 0.046(2) 0.0260(19) -0.0028(15) -0.0098(16) -0.0202(17) C3 0.064(2) 0.0302(17) 0.0231(18) 0.0017(14) -0.0018(15) 0.0032(15) C4 0.0307(14) 0.0229(14) 0.0208(16) 0.0015(11) 0.0005(11) -0.0036(11) C5 0.0187(11) 0.0171(13) 0.0200(15) 0.0010(10) -0.0007(10) -0.0049(10) C6 0.0249(12) 0.0143(12) 0.0203(15) 0.0028(10) -0.0027(10) -0.0042(10) C7 0.0170(11) 0.0159(12) 0.0231(15) -0.0023(10) 0.0008(10) -0.0050(10) C8 0.0180(11) 0.0163(12) 0.0199(15) 0.0007(10) -0.0028(10) -0.0039(9) C9 0.0180(11) 0.0149(12) 0.0242(15) 0.0015(10) -0.0021(10) -0.0033(10) C10 0.0202(11) 0.0152(12) 0.0216(15) -0.0008(10) -0.0013(10) -0.0034(10) C11 0.0343(14) 0.0146(13) 0.0254(17) -0.0013(11) 0.0025(12) -0.0007(11) C12 0.0458(16) 0.0128(13) 0.0266(17) 0.0015(11) 0.0013(13) -0.0038(12) C13 0.0291(13) 0.0198(13) 0.0214(15) 0.0008(11) 0.0005(11) -0.0062(11) C14 0.0178(11) 0.0177(13) 0.0222(15) -0.0003(11) -0.0012(10) -0.0026(10) C15 0.0297(13) 0.0144(13) 0.0270(17) -0.0010(11) 0.0017(11) -0.0023(11) C16 0.0208(12) 0.0170(13) 0.0258(16) -0.0025(11) -0.0017(10) -0.0014(10) C17 0.0308(13) 0.0178(13) 0.0244(16) -0.0054(11) 0.0029(11) -0.0022(11) C18 0.0383(15) 0.0247(15) 0.0299(18) -0.0060(13) 0.0118(13) -0.0036(12) C19 0.0444(16) 0.0209(14) 0.0328(19) -0.0099(13) 0.0104(13) -0.0075(12) C20 0.0479(18) 0.0385(19) 0.037(2) -0.0147(15) -0.0108(15) -0.0015(15) C21 0.0289(15) 0.046(2) 0.045(2) -0.0094(16) 0.0004(14) -0.0053(14) C22 0.0256(13) 0.0313(16) 0.041(2) -0.0077(14) -0.0043(13) -0.0024(12) C23 0.0276(14) 0.0275(16) 0.046(2) -0.0107(14) -0.0021(13) -0.0084(12) C24 0.0302(15) 0.0402(19) 0.053(2) 0.0022(16) -0.0062(14) -0.0143(14) C25 0.0371(16) 0.048(2) 0.032(2) -0.0018(15) -0.0089(13) -0.0096(14) N1 0.0241(11) 0.0263(12) 0.0289(15) 0.0015(10) -0.0005(10) -0.0022(9) O1 0.0261(9) 0.0166(9) 0.0219(11) -0.0009(7) 0.0017(7) -0.0030(7) O2 0.0263(9) 0.0143(9) 0.0189(10) 0.0004(7) 0.0011(7) -0.0024(7) O3 0.0277(9) 0.0136(9) 0.0222(11) -0.0009(7) 0.0022(7) -0.0024(7) O4 0.0368(10) 0.0172(9) 0.0215(11) 0.0001(8) 0.0040(8) -0.0045(8) O5 0.0364(11) 0.0533(14) 0.0537(16) -0.0029(12) 0.0040(10) -0.0217(11) Cu1 0.02665(17) 0.01350(17) 0.0209(2) 0.00021(12) 0.00349(12) -0.00196(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 C1 C4 1.543(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.533(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.526(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.531(4) . ? C5 O1 1.271(3) . ? C5 C6 1.410(3) . ? C6 C7 1.394(4) . ? C6 H6 0.9500 . ? C7 O2 1.284(3) . ? C7 C8 1.500(3) . ? C8 C9 1.395(3) . ? C8 C13 1.400(3) . ? C9 C10 1.401(3) . ? C9 H9 0.9500 . ? C10 C11 1.403(3) . ? C10 C14 1.501(3) . ? C11 C12 1.383(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.282(3) . ? C14 C15 1.400(4) . ? C15 C16 1.402(4) . ? C15 H15 0.9500 . ? C16 O4 1.278(3) . ? C16 C17 1.535(4) . ? C17 C20 1.532(4) . ? C17 C19 1.541(4) . ? C17 C18 1.546(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O5 1.432(3) . ? C21 C22 1.492(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N1 1.470(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N1 1.497(3) . ? C23 C24 1.510(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O5 1.410(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N1 1.456(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O1 Cu1 1.9288(17) . ? O2 Cu1 1.9266(17) . ? O3 Cu1 1.9447(17) 2_665 ? O4 Cu1 1.9302(18) 2_665 ? Cu1 O4 1.9302(18) 2_665 ? Cu1 O3 1.9447(17) 2_665 ? N1 Cu1 2.492(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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 C4 C5 114.3(2) . . ? C3 C4 C2 108.9(3) . . ? C5 C4 C2 107.5(2) . . ? C3 C4 C1 109.3(2) . . ? C5 C4 C1 107.4(2) . . ? C2 C4 C1 109.3(3) . . ? O1 C5 C6 123.7(2) . . ? O1 C5 C4 114.3(2) . . ? C6 C5 C4 122.0(2) . . ? C7 C6 C5 124.6(2) . . ? C7 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? O2 C7 C6 125.5(2) . . ? O2 C7 C8 114.5(2) . . ? C6 C7 C8 120.0(2) . . ? C9 C8 C13 118.5(2) . . ? C9 C8 C7 119.1(2) . . ? C13 C8 C7 122.4(2) . . ? C8 C9 C10 121.8(2) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C9 C10 C11 118.4(2) . . ? C9 C10 C14 118.5(2) . . ? C11 C10 C14 123.0(2) . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 121.3(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 120.1(2) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? O3 C14 C15 124.3(2) . . ? O3 C14 C10 115.0(2) . . ? C15 C14 C10 120.7(2) . . ? C14 C15 C16 124.6(2) . . ? C14 C15 H15 117.7 . . ? C16 C15 H15 117.7 . . ? O4 C16 C15 124.2(2) . . ? O4 C16 C17 113.6(2) . . ? C15 C16 C17 122.1(2) . . ? C20 C17 C16 107.5(2) . . ? C20 C17 C19 110.1(2) . . ? C16 C17 C19 113.9(2) . . ? C20 C17 C18 109.6(2) . . ? C16 C17 C18 107.6(2) . . ? C19 C17 C18 108.1(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 C21 C22 111.4(3) . . ? O5 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? O5 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? N1 C22 C21 111.5(2) . . ? N1 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? N1 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? N1 C23 C24 110.0(2) . . ? N1 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? N1 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? O5 C24 C23 111.8(2) . . ? O5 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? O5 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 N1 C22 110.4(2) . . ? C25 N1 C23 107.3(2) . . ? C22 N1 C23 108.0(2) . . ? C5 O1 Cu1 126.47(16) . . ? C7 O2 Cu1 125.24(17) . . ? C14 O3 Cu1 126.96(16) . 2_665 ? C16 O4 Cu1 127.75(17) . 2_665 ? C24 O5 C21 109.1(2) . . ? O2 Cu1 O1 92.73(7) . . ? O2 Cu1 O4 174.01(7) . 2_665 ? O1 Cu1 O4 86.24(7) . 2_665 ? O2 Cu1 O3 88.14(7) . 2_665 ? O1 Cu1 O3 166.89(7) . 2_665 ? O4 Cu1 O3 91.53(7) 2_665 2_665 ? N1 Cu1 O5 167.59(6) . 1_655 ? O2 Cu1 N1 89.91(7) . . ? O1 Cu1 N1 101.67(7) . . ? O4 Cu1 N1 96.08(8) 2_665 . ? O3 Cu1 N1 91.41(7) 2_665 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C4 C5 O1 -175.6(2) . . . . ? C2 C4 C5 O1 -54.6(3) . . . . ? C1 C4 C5 O1 62.9(3) . . . . ? C3 C4 C5 C6 5.6(3) . . . . ? C2 C4 C5 C6 126.6(3) . . . . ? C1 C4 C5 C6 -115.9(3) . . . . ? O1 C5 C6 C7 1.6(4) . . . . ? C4 C5 C6 C7 -179.8(2) . . . . ? C5 C6 C7 O2 2.6(4) . . . . ? C5 C6 C7 C8 -179.4(2) . . . . ? O2 C7 C8 C9 16.0(3) . . . . ? C6 C7 C8 C9 -162.2(2) . . . . ? O2 C7 C8 C13 -163.6(2) . . . . ? C6 C7 C8 C13 18.2(3) . . . . ? C13 C8 C9 C10 -0.9(3) . . . . ? C7 C8 C9 C10 179.4(2) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C8 C9 C10 C14 177.9(2) . . . . ? C9 C10 C11 C12 1.8(4) . . . . ? C14 C10 C11 C12 -176.8(2) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C8 -0.6(4) . . . . ? C9 C8 C13 C12 1.6(4) . . . . ? C7 C8 C13 C12 -178.7(2) . . . . ? C9 C10 C14 O3 5.0(3) . . . . ? C11 C10 C14 O3 -176.4(2) . . . . ? C9 C10 C14 C15 -174.0(2) . . . . ? C11 C10 C14 C15 4.6(4) . . . . ? O3 C14 C15 C16 1.0(4) . . . . ? C10 C14 C15 C16 179.8(2) . . . . ? C14 C15 C16 O4 2.5(4) . . . . ? C14 C15 C16 C17 -176.4(2) . . . . ? O4 C16 C17 C20 -62.2(3) . . . . ? C15 C16 C17 C20 116.7(3) . . . . ? O4 C16 C17 C19 175.6(2) . . . . ? C15 C16 C17 C19 -5.5(3) . . . . ? O4 C16 C17 C18 55.7(3) . . . . ? C15 C16 C17 C18 -125.3(3) . . . . ? O5 C21 C22 N1 -58.8(3) . . . . ? N1 C23 C24 O5 59.0(3) . . . . ? C21 C22 N1 C25 172.3(2) . . . . ? C21 C22 N1 C23 55.3(3) . . . . ? C24 C23 N1 C25 -173.7(2) . . . . ? C24 C23 N1 C22 -54.7(3) . . . . ? C6 C5 O1 Cu1 -12.7(3) . . . . ? C4 C5 O1 Cu1 168.60(15) . . . . ? C6 C7 O2 Cu1 4.8(3) . . . . ? C8 C7 O2 Cu1 -173.33(13) . . . . ? C15 C14 O3 Cu1 -7.9(3) . . . 2_665 ? C10 C14 O3 Cu1 173.17(14) . . . 2_665 ? C15 C16 O4 Cu1 1.4(4) . . . 2_665 ? C17 C16 O4 Cu1 -179.62(15) . . . 2_665 ? C23 C24 O5 C21 -60.1(3) . . . . ? C22 C21 O5 C24 59.5(3) . . . . ? C7 O2 Cu1 O1 -10.91(18) . . . . ? C7 O2 Cu1 O3 156.01(18) . . . 2_665 ? C5 O1 Cu1 O2 14.99(19) . . . . ? C5 O1 Cu1 O4 -159.10(19) . . . 2_665 ? C5 O1 Cu1 O3 -78.6(4) . . . 2_665 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.630 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.085 # Attachment 'Cu_mmorph_H_press_1.CIF' data_Cu_mmorph_H_press_1.CIF _database_code_depnum_ccdc_archive 'CCDC 754702' #TrackingRef 'Cu_mmorph_H_press_1.CIF' _publ_section_exptl_refinement ; ; #end of refcif _cell_length_a 6.9932(11) _cell_length_b 11.2678(18) _cell_length_c 16.466(7) _cell_angle_alpha 83.88(2) _cell_angle_beta 84.62(2) _cell_angle_gamma 73.405(11) _cell_volume 1233.6(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.2980 0.6520 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0040 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C50 H70 Cu2 N2 O10 # Dc = 1.33 Fooo = 522.00 Mu = 9.20 M = 493.10 # Found Formula = C50 H70 Cu2 N2 O10 # Dc = 1.33 FOOO = 522.00 Mu = 9.20 M = 493.10 _chemical_formula_sum 'C50 H70 Cu2 N2 O10' _chemical_formula_moiety 'C50 H70 Cu2 N2 O10' _chemical_compound_source ? _chemical_formula_weight 986.21 _cell_measurement_reflns_used 1830 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.920 # Sheldrick geometric approximatio 0.83 0.91 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.10 _exptl_absorpt_correction_T_max 0.91 _diffrn_measurement_device synchrotron _diffrn_measurement_device_type 'Apex II' _diffrn_radiation_monochromator silicon _diffrn_radiation_type ' synchrotron ' _diffrn_radiation_wavelength 0.49200 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 186000 _diffrn_reflns_number 5388 _reflns_number_total 1732 _diffrn_reflns_av_R_equivalents 0.070 # Number of reflections with Friedels Law is 1732 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4265 _diffrn_reflns_theta_min 1.507 _diffrn_reflns_theta_max 16.901 _diffrn_measured_fraction_theta_max 0.405 _diffrn_reflns_theta_full 12.845 _diffrn_measured_fraction_theta_full 0.442 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 8 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.32 _refine_diff_density_max 0.35 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1667 _refine_ls_number_restraints 193 _refine_ls_number_parameters 290 #_oxford_refine_ls_R_factor_ref 0.1134 _refine_ls_wR_factor_ref 0.1182 _refine_ls_goodness_of_fit_ref 1.1686 _refine_ls_shift/su_max 0.000217 # The values computed from all data #_oxford_reflns_number_all 1667 _refine_ls_R_factor_all 0.1134 _refine_ls_wR_factor_all 0.1182 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1177 _refine_ls_R_factor_gt 0.0891 _refine_ls_wR_factor_gt 0.0992 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.90 0.670 1.69 ; _refine_special_details ; 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.41 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 12.85 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.44 088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.75 341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 24 910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 21 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.591 936 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 14 This is a high pressure data set. Completeness is low due to shading of the diffraction pattern by the steel body of the diamond anvil cell. This has in turn affected the data to parameter ratio, etc. 242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 C4 is the pivot atom in a tBu group 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 193 Confirmed 234_ALERT_4_C Large Hirshfeld Difference C2 -- C4 .. 0.16 Ang. 234_ALERT_4_C Large Hirshfeld Difference C16 -- C17 .. 0.22 Ang. 731_ALERT_1_C Bond Calc 1.53(3), Rep 1.534(10) ...... 3.00 su-Ra C21 -C22 1.555 1.555 Restraints have been used 952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 11 Values reported are from sortav merging. 092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang. This is synchrotron data 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Confirmed RT data collection. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? No action taken 929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ? The Chebychev scheme has been used ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.23746(13) 0.56480(7) 0.20466(13) 0.0605 1.0000 Uani . U . . . . . C1 C 0.095(2) 0.3184(14) 0.437(2) 0.1051 1.0000 Uani . U . . . . . C2 C 0.388(2) 0.3979(12) 0.463(2) 0.1058 1.0000 Uani . U . . . . . C3 C 0.437(2) 0.1773(11) 0.435(2) 0.1061 1.0000 Uani . U . . . . . C4 C 0.3227(17) 0.3108(9) 0.4152(17) 0.0781 1.0000 Uani . U . . . . . C5 C 0.3277(11) 0.3532(7) 0.3266(14) 0.0600 1.0000 Uani . U . . . . . C6 C 0.4127(13) 0.2746(7) 0.2630(15) 0.0625 1.0000 Uani . U . . . . . C7 C 0.4228(11) 0.3088(6) 0.1846(14) 0.0535 1.0000 Uani . U . . . . . C8 C 0.5223(10) 0.2148(6) 0.1259(12) 0.0572 1.0000 Uani . U . . . . . C9 C 0.5821(11) 0.2521(6) 0.0466(12) 0.0559 1.0000 Uani . U . . . . . C10 C 0.6776(10) 0.1709(6) -0.0136(11) 0.0535 1.0000 Uani . U . . . . . C11 C 0.7184(13) 0.0431(7) 0.0113(14) 0.0653 1.0000 Uani . U . . . . . C12 C 0.6509(14) 0.0034(7) 0.0849(15) 0.0710 1.0000 Uani . U . . . . . C13 C 0.5599(12) 0.0870(7) 0.1444(13) 0.0644 1.0000 Uani . U . . . . . C14 C 0.7337(11) 0.2197(6) -0.0967(13) 0.0632 1.0000 Uani . U . . . . . C15 C 0.8077(13) 0.1402(6) -0.1589(14) 0.0684 1.0000 Uani . U . . . . . C16 C 0.8607(11) 0.1769(6) -0.2348(13) 0.0650 1.0000 Uani . U . . . . . C17 C 0.9374(14) 0.0852(6) -0.3036(13) 0.0516 1.0000 Uani . U . . . . . C18 C 1.1328(17) 0.1018(9) -0.3434(15) 0.0634 1.0000 Uani . U . . . . . C19 C 0.9691(17) -0.0513(8) -0.2682(14) 0.0598 1.0000 Uani . U . . . . . C20 C 0.7893(19) 0.1220(10) -0.3652(18) 0.0736 1.0000 Uani . U . . . . . C21 C -0.2748(16) 0.5919(11) 0.2906(13) 0.0902 1.0000 Uani D U . . . . . C22 C -0.2560(14) 0.6583(9) 0.2052(12) 0.0786 1.0000 Uani D U . . . . . C23 C -0.1385(14) 0.4608(9) 0.1498(16) 0.0762 1.0000 Uani . U . . . . . C24 C -0.1615(14) 0.3987(10) 0.2408(16) 0.0788 1.0000 Uani . U . . . . . C25 C -0.0886(16) 0.6446(11) 0.0664(18) 0.0849 1.0000 Uani . U . . . . . N1 N -0.0938(10) 0.5796(6) 0.1549(12) 0.0668 1.0000 Uani . U . . . . . O1 O 0.2328(8) 0.4697(5) 0.3073(9) 0.0657 1.0000 Uani . U . . . . . O2 O 0.3525(8) 0.4187(4) 0.1478(8) 0.0582 1.0000 Uani . U . . . . . O3 O 0.6971(8) 0.3389(4) -0.1104(9) 0.0696 1.0000 Uani . U . . . . . O4 O 0.8503(9) 0.2899(5) -0.2656(9) 0.0724 1.0000 Uani . U . . . . . O5 O -0.3172(11) 0.4735(8) 0.2800(11) 0.0930 1.0000 Uani . U . . . . . H11 H 0.0562 0.2604 0.4042 0.1210 1.0000 Uiso R . . . . . . H12 H 0.0759 0.2936 0.4966 0.1210 1.0000 Uiso R . . . . . . H13 H 0.0104 0.4051 0.4241 0.1210 1.0000 Uiso R . . . . . . H21 H 0.5321 0.3923 0.4478 0.1241 1.0000 Uiso R . . . . . . H22 H 0.3705 0.3736 0.5228 0.1241 1.0000 Uiso R . . . . . . H23 H 0.3050 0.4851 0.4504 0.1241 1.0000 Uiso R . . . . . . H31 H 0.5836 0.1670 0.4221 0.1165 1.0000 Uiso R . . . . . . H32 H 0.4126 0.1538 0.4944 0.1165 1.0000 Uiso R . . . . . . H33 H 0.3920 0.1225 0.4016 0.1165 1.0000 Uiso R . . . . . . H61 H 0.4699 0.1843 0.2799 0.0734 1.0000 Uiso R . . . . . . H91 H 0.5555 0.3434 0.0312 0.0638 1.0000 Uiso R . . . . . . H111 H 0.7984 -0.0189 -0.0268 0.0750 1.0000 Uiso R . . . . . . H121 H 0.6664 -0.0874 0.0984 0.0816 1.0000 Uiso R . . . . . . H131 H 0.5212 0.0543 0.2005 0.0752 1.0000 Uiso R . . . . . . H151 H 0.8215 0.0496 -0.1456 0.0779 1.0000 Uiso R . . . . . . H181 H 1.1811 0.0433 -0.3874 0.0772 1.0000 Uiso R . . . . . . H182 H 1.1113 0.1893 -0.3681 0.0772 1.0000 Uiso R . . . . . . H183 H 1.2350 0.0836 -0.3018 0.0772 1.0000 Uiso R . . . . . . H191 H 1.0175 -0.1073 -0.3135 0.0745 1.0000 Uiso R . . . . . . H192 H 1.0705 -0.0724 -0.2262 0.0745 1.0000 Uiso R . . . . . . H193 H 0.8395 -0.0627 -0.2424 0.0745 1.0000 Uiso R . . . . . . H201 H 0.8331 0.0654 -0.4104 0.0848 1.0000 Uiso R . . . . . . H202 H 0.7782 0.2095 -0.3878 0.0848 1.0000 Uiso R . . . . . . H203 H 0.6562 0.1160 -0.3400 0.0848 1.0000 Uiso R . . . . . . H211 H -0.3882 0.6447 0.3238 0.1061 1.0000 Uiso R . . . . . . H212 H -0.1483 0.5760 0.3188 0.1061 1.0000 Uiso R . . . . . . H221 H -0.2215 0.7365 0.2127 0.0901 1.0000 Uiso R . . . . . . H222 H -0.3852 0.6795 0.1783 0.0901 1.0000 Uiso R . . . . . . H231 H -0.2661 0.4759 0.1225 0.0904 1.0000 Uiso R . . . . . . H232 H -0.0272 0.4043 0.1178 0.0904 1.0000 Uiso R . . . . . . H251 H 0.0202 0.5910 0.0317 0.1006 1.0000 Uiso R . . . . . . H252 H -0.0624 0.7270 0.0681 0.1006 1.0000 Uiso R . . . . . . H253 H -0.2201 0.6570 0.0427 0.1006 1.0000 Uiso R . . . . . . H241 H -0.0375 0.3887 0.2696 0.0958 1.0000 Uiso R . . . . . . H242 H -0.1846 0.3155 0.2389 0.0958 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0573(7) 0.0326(6) 0.086(5) -0.0059(8) 0.0104(9) -0.0085(4) C1 0.102(6) 0.108(7) 0.090(17) -0.001(9) 0.024(8) -0.017(6) C2 0.128(7) 0.090(6) 0.094(17) -0.011(8) 0.010(9) -0.025(6) C3 0.117(7) 0.083(6) 0.089(17) -0.002(8) 0.012(9) 0.010(5) C4 0.083(4) 0.058(4) 0.088(14) -0.007(5) 0.015(6) -0.019(3) C5 0.047(3) 0.043(3) 0.091(11) -0.006(4) -0.001(5) -0.014(3) C6 0.056(3) 0.038(3) 0.093(11) -0.002(5) -0.001(5) -0.014(3) C7 0.044(3) 0.028(3) 0.087(10) -0.006(4) 0.005(4) -0.011(2) C8 0.043(3) 0.039(3) 0.090(10) -0.007(4) 0.009(4) -0.015(2) C9 0.046(3) 0.030(3) 0.086(12) -0.010(4) 0.012(5) -0.005(2) C10 0.039(3) 0.034(3) 0.086(13) -0.013(5) 0.006(5) -0.009(2) C11 0.062(4) 0.035(3) 0.092(13) -0.012(5) 0.003(5) -0.003(3) C12 0.078(4) 0.035(3) 0.092(13) -0.008(5) 0.005(6) -0.005(3) C13 0.060(3) 0.036(3) 0.093(12) -0.003(5) -0.003(5) -0.008(3) C14 0.047(3) 0.031(3) 0.110(14) -0.008(5) -0.005(5) -0.009(3) C15 0.064(4) 0.029(3) 0.108(14) -0.006(5) 0.010(5) -0.012(3) C16 0.053(3) 0.031(3) 0.108(14) -0.003(5) 0.005(5) -0.011(3) C17 0.081(5) 0.034(3) 0.03(2) -0.005(5) 0.020(7) -0.006(3) C18 0.095(5) 0.056(4) 0.04(2) 0.004(6) 0.001(7) -0.018(4) C19 0.098(5) 0.046(4) 0.03(2) -0.012(6) 0.002(7) -0.017(4) C20 0.106(5) 0.064(4) 0.03(2) -0.006(5) 0.002(7) 0.001(4) C21 0.068(4) 0.094(5) 0.104(13) -0.003(7) 0.010(6) -0.022(4) C22 0.059(4) 0.066(4) 0.102(12) -0.005(6) -0.005(6) -0.004(3) C23 0.060(4) 0.066(4) 0.101(12) -0.010(6) -0.006(6) -0.015(3) C24 0.060(4) 0.078(5) 0.103(13) -0.005(6) -0.003(6) -0.029(4) C25 0.072(5) 0.078(5) 0.098(13) -0.004(7) -0.013(7) -0.010(4) N1 0.053(3) 0.052(3) 0.098(9) -0.012(4) -0.008(4) -0.014(2) O1 0.061(3) 0.040(2) 0.089(9) 0.000(4) 0.008(4) -0.008(2) O2 0.055(2) 0.029(2) 0.082(9) 0.002(3) 0.001(4) -0.0027(18) O3 0.061(3) 0.033(2) 0.112(14) -0.003(4) 0.000(4) -0.010(2) O4 0.066(3) 0.037(2) 0.109(15) 0.001(4) 0.002(5) -0.011(2) O5 0.073(3) 0.105(4) 0.106(13) 0.001(6) 0.011(5) -0.042(3) _refine_ls_extinction_coef 21839.791 _refine_ls_extinction_method 'Larson (1970), Equation 22' #_oxford_refine_ls_scale 1.819(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . O4 2_665 1.929(10) yes Cu1 . O3 2_665 1.895(11) yes Cu1 . N1 . 2.484(10) yes Cu1 . O1 . 1.905(13) yes Cu1 . O2 . 1.914(8) yes C1 . C4 . 1.576(17) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C1 . H13 . 1.000 no C2 . C4 . 1.51(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C2 . H23 . 1.000 no C3 . C4 . 1.505(17) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C3 . H33 . 1.000 no C4 . C5 . 1.49(4) yes C5 . C6 . 1.42(3) yes C5 . O1 . 1.311(11) yes C6 . C7 . 1.31(3) yes C6 . H61 . 1.000 no C7 . C8 . 1.49(2) yes C7 . O2 . 1.300(14) yes C8 . C9 . 1.39(3) yes C8 . C13 . 1.393(11) yes C9 . C10 . 1.41(2) yes C9 . H91 . 1.000 no C10 . C11 . 1.408(12) yes C10 . C14 . 1.48(3) yes C11 . C12 . 1.34(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.41(2) yes C12 . H121 . 1.000 no C13 . H131 . 1.000 no C14 . C15 . 1.40(2) yes C14 . O3 . 1.292(9) yes C15 . C16 . 1.33(3) yes C15 . H151 . 1.000 no C16 . C17 . 1.57(2) yes C16 . O4 . 1.303(11) yes C17 . C18 . 1.512(15) yes C17 . C19 . 1.547(14) yes C17 . C20 . 1.46(3) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . C22 . 1.534(10) yes C21 . O5 . 1.477(16) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . N1 . 1.471(17) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . C24 . 1.60(3) yes C23 . N1 . 1.471(13) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . O5 . 1.332(19) yes C24 . H241 . 1.000 no C24 . H242 . 1.000 no C25 . N1 . 1.56(3) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C25 . H253 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 2_665 Cu1 . O3 2_665 90.9(4) yes O4 2_665 Cu1 . N1 . 96.4(4) yes O3 2_665 Cu1 . N1 . 91.5(4) yes O4 2_665 Cu1 . O1 . 86.7(5) yes O3 2_665 Cu1 . O1 . 166.0(3) yes N1 . Cu1 . O1 . 102.5(4) yes O4 2_665 Cu1 . O2 . 173.9(3) yes O3 2_665 Cu1 . O2 . 88.8(4) yes N1 . Cu1 . O2 . 89.7(3) yes O1 . Cu1 . O2 . 92.1(4) yes C4 . C1 . H11 . 109.2 no C4 . C1 . H12 . 109.1 no H11 . C1 . H12 . 109.5 no C4 . C1 . H13 . 110.1 no H11 . C1 . H13 . 109.5 no H12 . C1 . H13 . 109.5 no C4 . C2 . H21 . 109.6 no C4 . C2 . H22 . 109.1 no H21 . C2 . H22 . 109.5 no C4 . C2 . H23 . 109.7 no H21 . C2 . H23 . 109.5 no H22 . C2 . H23 . 109.5 no C4 . C3 . H31 . 109.6 no C4 . C3 . H32 . 109.1 no H31 . C3 . H32 . 109.5 no C4 . C3 . H33 . 109.7 no H31 . C3 . H33 . 109.5 no H32 . C3 . H33 . 109.5 no C2 . C4 . C3 . 112(2) yes C2 . C4 . C1 . 111.0(17) yes C3 . C4 . C1 . 106.2(11) yes C2 . C4 . C5 . 109.9(14) yes C3 . C4 . C5 . 115(2) yes C1 . C4 . C5 . 103.1(19) yes C4 . C5 . C6 . 124.6(10) yes C4 . C5 . O1 . 116.2(16) yes C6 . C5 . O1 . 119.0(19) yes C5 . C6 . C7 . 126.3(10) yes C5 . C6 . H61 . 116.7 no C7 . C6 . H61 . 117.0 no C6 . C7 . C8 . 119.6(10) yes C6 . C7 . O2 . 128.3(14) yes C8 . C7 . O2 . 112.1(17) yes C7 . C8 . C9 . 120.4(8) yes C7 . C8 . C13 . 124.0(16) yes C9 . C8 . C13 . 115.7(14) yes C8 . C9 . C10 . 124.9(8) yes C8 . C9 . H91 . 117.6 no C10 . C9 . H91 . 117.6 no C9 . C10 . C11 . 115.8(15) yes C9 . C10 . C14 . 120.9(8) yes C11 . C10 . C14 . 123.3(14) yes C10 . C11 . C12 . 121.1(14) yes C10 . C11 . H111 . 119.4 no C12 . C11 . H111 . 119.4 no C11 . C12 . C13 . 121.2(9) yes C11 . C12 . H121 . 119.5 no C13 . C12 . H121 . 119.3 no C12 . C13 . C8 . 120.9(17) yes C12 . C13 . H131 . 119.6 no C8 . C13 . H131 . 119.5 no C10 . C14 . C15 . 120.8(8) yes C10 . C14 . O3 . 117.1(14) yes C15 . C14 . O3 . 121.9(16) yes C14 . C15 . C16 . 124.3(8) yes C14 . C15 . H151 . 118.0 no C16 . C15 . H151 . 117.7 no C15 . C16 . C17 . 122.7(8) yes C15 . C16 . O4 . 127.7(14) yes C17 . C16 . O4 . 109.5(15) yes C16 . C17 . C18 . 109.2(10) yes C16 . C17 . C19 . 111.2(15) yes C18 . C17 . C19 . 109.4(8) yes C16 . C17 . C20 . 106.6(9) yes C18 . C17 . C20 . 107.9(17) yes C19 . C17 . C20 . 112.4(11) yes C17 . C18 . H181 . 109.0 no C17 . C18 . H182 . 109.4 no H181 . C18 . H182 . 109.5 no C17 . C18 . H183 . 110.1 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no C17 . C19 . H191 . 109.2 no C17 . C19 . H192 . 109.8 no H191 . C19 . H192 . 109.5 no C17 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C17 . C20 . H201 . 109.0 no C17 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no C17 . C20 . H203 . 109.9 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no C22 . C21 . O5 . 107.5(14) yes C22 . C21 . H211 . 109.4 no O5 . C21 . H211 . 109.5 no C22 . C21 . H212 . 110.4 no O5 . C21 . H212 . 110.5 no H211 . C21 . H212 . 109.5 no C21 . C22 . N1 . 109.9(10) yes C21 . C22 . H221 . 107.0 no N1 . C22 . H221 . 109.1 no C21 . C22 . H222 . 110.6 no N1 . C22 . H222 . 110.7 no H221 . C22 . H222 . 109.5 no C24 . C23 . N1 . 108.2(18) yes C24 . C23 . H231 . 109.6 no N1 . C23 . H231 . 109.8 no C24 . C23 . H232 . 109.8 no N1 . C23 . H232 . 110.0 no H231 . C23 . H232 . 109.5 no C23 . C24 . O5 . 107.9(12) yes C23 . C24 . H241 . 109.9 no O5 . C24 . H241 . 109.7 no C23 . C24 . H242 . 109.8 no O5 . C24 . H242 . 110.0 no H241 . C24 . H242 . 109.5 no N1 . C25 . H251 . 109.2 no N1 . C25 . H252 . 109.8 no H251 . C25 . H252 . 109.5 no N1 . C25 . H253 . 109.4 no H251 . C25 . H253 . 109.5 no H252 . C25 . H253 . 109.5 no C25 . N1 . C23 . 107.9(17) yes C25 . N1 . C22 . 108.8(10) yes C23 . N1 . C22 . 108.5(9) yes C25 . N1 . Cu1 . 104.5(6) yes C23 . N1 . Cu1 . 115.9(7) yes C22 . N1 . Cu1 . 110.8(10) yes C5 . O1 . Cu1 . 128.8(13) yes C7 . O2 . Cu1 . 123.5(13) yes C14 . O3 . Cu1 2_665 129.7(12) yes C16 . O4 . Cu1 2_665 124.8(13) yes C21 . O5 . C24 . 110.2(8) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C21 . H212 . O1 . 144 1.00 2.59 3.45(2) yes C24 . H241 . O1 . 151 1.00 2.47 3.38(2) yes # Attachment 'Cu_mmorph_H_press_2.CIF' data_Cu_mmorph_H_press_2.CIF _database_code_depnum_ccdc_archive 'CCDC 754703' #TrackingRef 'Cu_mmorph_H_press_2.CIF' _publ_section_exptl_refinement ; ; #end of refcif _cell_length_a 6.8237(5) _cell_length_b 11.0237(8) _cell_length_c 16.053(3) _cell_angle_alpha 84.420(12) _cell_angle_beta 85.462(12) _cell_angle_gamma 73.617(5) _cell_volume 1151.3(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0040 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.2980 0.6520 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C46 H46 Cu2 N2 O10 # Dc = 1.32 Fooo = 522.00 Mu = 9.80 M = 456.99 # Found Formula = C50 H70 Cu2 N2 O10 # Dc = 1.42 FOOO = 522.00 Mu = 9.85 M = 493.10 _chemical_formula_sum 'C50 H70 Cu2 N2 O10' _chemical_formula_moiety 'C50 H70 Cu2 N2 O10' _chemical_compound_source ? _chemical_formula_weight 986.21 _cell_measurement_reflns_used 2053 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.985 # Sheldrick geometric approximatio 0.82 0.91 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.11 _exptl_absorpt_correction_T_max 0.91 _diffrn_measurement_device synchrotron _diffrn_measurement_device_type APEX-II _diffrn_radiation_monochromator silicon _diffrn_radiation_type ' synchrotron ' _diffrn_radiation_wavelength 0.49200 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 910000 _diffrn_reflns_number 5006 _reflns_number_total 1553 _diffrn_reflns_av_R_equivalents 0.082 # Number of reflections with Friedels Law is 1553 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3898 _diffrn_reflns_theta_min 1.544 _diffrn_reflns_theta_max 16.781 _diffrn_measured_fraction_theta_max 0.401 _diffrn_reflns_theta_full 12.921 _diffrn_measured_fraction_theta_full 0.446 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 7 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.28 _refine_diff_density_max 0.29 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1519 _refine_ls_number_restraints 192 _refine_ls_number_parameters 290 #_oxford_refine_ls_R_factor_ref 0.0679 _refine_ls_wR_factor_ref 0.0730 _refine_ls_goodness_of_fit_ref 1.1808 _refine_ls_shift/su_max 0.000210 # The values computed from all data #_oxford_reflns_number_all 1519 _refine_ls_R_factor_all 0.0679 _refine_ls_wR_factor_all 0.0730 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1231 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_gt 0.0653 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.31 0.193 1.35 ; _refine_special_details ; 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.40 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 12.92 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.45 088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.24 910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 18 911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.587 645 023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6].. 16.78 Deg. 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 15 913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 10 This is a high pressure data set. Completeness is low due to shading of the diffraction pattern by the steel body of the diamond anvil cell. This has in turn affected the data to parameter ratio, etc. 413_ALERT_2_C Short Inter XH3 .. XHn H12 .. H182 .. 2.11 Ang. At high pressure short contacts are expected 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 192 Confirmed 152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? This is probably a rounding error, values reported has been confirmed from integration output. 952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 11 Values reported are from sortav merging. 092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang. This is synchrotron data 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Confirmed RT data collection. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? No action taken 929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ? Chebychev weights have been used. ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.0788(9) 0.3284(6) 0.4554(10) 0.0510 1.0000 Uani . U . . . . . C2 C 0.3951(12) 0.3968(6) 0.4696(12) 0.0570 1.0000 Uani . U . . . . . C3 C 0.4280(10) 0.1725(5) 0.4439(10) 0.0518 1.0000 Uani . U . . . . . C4 C 0.3046(8) 0.3104(5) 0.4183(10) 0.0348 1.0000 Uani . U . . . . . C5 C 0.3088(7) 0.3541(5) 0.3289(9) 0.0289 1.0000 Uani . U . . . . . C6 C 0.3990(8) 0.2710(5) 0.2677(10) 0.0304 1.0000 Uani . U . . . . . C7 C 0.4166(7) 0.3032(5) 0.1846(10) 0.0297 1.0000 Uani . U . . . . . C8 C 0.5214(7) 0.2091(4) 0.1215(8) 0.0275 1.0000 Uani . U . . . . . C9 C 0.5866(7) 0.2477(4) 0.0461(8) 0.0279 1.0000 Uani . U . . . . . C10 C 0.6882(7) 0.1624(4) -0.0143(8) 0.0321 1.0000 Uani . U . . . . . C11 C 0.7290(8) 0.0321(4) 0.0112(9) 0.0348 1.0000 Uani . U . . . . . C12 C 0.6609(8) -0.0081(4) 0.0865(9) 0.0374 1.0000 Uani . U . . . . . C13 C 0.5568(7) 0.0780(4) 0.1451(8) 0.0332 1.0000 Uani . U . . . . . C14 C 0.7400(7) 0.2124(4) -0.0996(8) 0.0260 1.0000 Uani . U . . . . . C15 C 0.8240(8) 0.1325(4) -0.1621(9) 0.0299 1.0000 Uani . U . . . . . C16 C 0.8721(7) 0.1706(4) -0.2447(8) 0.0240 1.0000 Uani . U . . . . . C17 C 0.9501(8) 0.0780(5) -0.3139(9) 0.0441 1.0000 Uani . U . . . . . C18 C 1.1549(8) 0.0947(5) -0.3477(9) 0.0486 1.0000 Uani . U . . . . . C19 C 0.9853(10) -0.0618(5) -0.2810(9) 0.0509 1.0000 Uani . U . . . . . C20 C 0.7994(11) 0.1103(6) -0.3810(12) 0.0590 1.0000 Uani . U . . . . . C21 C -0.2956(9) 0.6040(6) 0.2887(11) 0.0566 1.0000 Uani . U . . . . . C22 C -0.2651(8) 0.6666(5) 0.2056(10) 0.0454 1.0000 Uani . U . . . . . C23 C -0.1485(8) 0.4599(5) 0.1538(10) 0.0443 1.0000 Uani . U . . . . . C24 C -0.1850(9) 0.4053(6) 0.2372(10) 0.0535 1.0000 Uani . U . . . . . C25 C -0.0953(10) 0.6399(7) 0.0715(11) 0.0544 1.0000 Uani . U . . . . . N1 N -0.1007(6) 0.5829(4) 0.1549(8) 0.0391 1.0000 Uani . U . . . . . O1 O 0.2170(5) 0.4699(3) 0.3128(6) 0.0342 1.0000 Uani . U . . . . . O2 O 0.3477(5) 0.4173(3) 0.1481(6) 0.0350 1.0000 Uani . U . . . . . O3 O 0.6976(5) 0.3347(3) -0.1111(6) 0.0339 1.0000 Uani . U . . . . . O4 O 0.8531(5) 0.2855(3) -0.2724(5) 0.0282 1.0000 Uani . U . . . . . O5 O -0.3438(7) 0.4864(4) 0.2824(7) 0.0639 1.0000 Uani . U . . . . . Cu1 Cu 0.23266(8) 0.56647(5) 0.20790(9) 0.0324 1.0000 Uani . U . . . . . H11 H 0.0120 0.2757 0.4265 0.0518 1.0000 Uiso R . . . . . . H12 H 0.0812 0.3017 0.5167 0.0518 1.0000 Uiso R . . . . . . H13 H 0.0005 0.4199 0.4468 0.0518 1.0000 Uiso R . . . . . . H21 H 0.5386 0.3894 0.4479 0.0640 1.0000 Uiso R . . . . . . H22 H 0.3909 0.3684 0.5300 0.0640 1.0000 Uiso R . . . . . . H23 H 0.3102 0.4866 0.4602 0.0640 1.0000 Uiso R . . . . . . H31 H 0.5723 0.1574 0.4229 0.0530 1.0000 Uiso R . . . . . . H32 H 0.4245 0.1605 0.5083 0.0530 1.0000 Uiso R . . . . . . H33 H 0.3641 0.1120 0.4234 0.0530 1.0000 Uiso R . . . . . . H61 H 0.4540 0.1794 0.2869 0.0393 1.0000 Uiso R . . . . . . H91 H 0.5622 0.3408 0.0310 0.0336 1.0000 Uiso R . . . . . . H111 H 0.8111 -0.0319 -0.0273 0.0415 1.0000 Uiso R . . . . . . H121 H 0.6839 -0.1011 0.1014 0.0445 1.0000 Uiso R . . . . . . H131 H 0.5112 0.0473 0.2025 0.0394 1.0000 Uiso R . . . . . . H151 H 0.8529 0.0392 -0.1469 0.0360 1.0000 Uiso R . . . . . . H181 H 1.2119 0.0361 -0.3931 0.0571 1.0000 Uiso R . . . . . . H182 H 1.1371 0.1843 -0.3712 0.0571 1.0000 Uiso R . . . . . . H183 H 1.2523 0.0746 -0.3016 0.0571 1.0000 Uiso R . . . . . . H191 H 1.0346 -0.1170 -0.3279 0.0704 1.0000 Uiso R . . . . . . H192 H 1.0887 -0.0837 -0.2370 0.0704 1.0000 Uiso R . . . . . . H193 H 0.8527 -0.0747 -0.2553 0.0704 1.0000 Uiso R . . . . . . H201 H 0.8480 0.0510 -0.4255 0.0585 1.0000 Uiso R . . . . . . H202 H 0.7852 0.1994 -0.4043 0.0585 1.0000 Uiso R . . . . . . H203 H 0.6640 0.1028 -0.3553 0.0585 1.0000 Uiso R . . . . . . H211 H -0.4120 0.6618 0.3206 0.0634 1.0000 Uiso R . . . . . . H212 H -0.1686 0.5867 0.3201 0.0634 1.0000 Uiso R . . . . . . H221 H -0.2263 0.7454 0.2123 0.0493 1.0000 Uiso R . . . . . . H222 H -0.3956 0.6887 0.1753 0.0493 1.0000 Uiso R . . . . . . H231 H -0.2732 0.4731 0.1216 0.0523 1.0000 Uiso R . . . . . . H232 H -0.0298 0.3995 0.1254 0.0523 1.0000 Uiso R . . . . . . H241 H -0.0570 0.3880 0.2675 0.0637 1.0000 Uiso R . . . . . . H242 H -0.2193 0.3239 0.2322 0.0637 1.0000 Uiso R . . . . . . H251 H 0.0153 0.5836 0.0378 0.0616 1.0000 Uiso R . . . . . . H252 H -0.0664 0.7238 0.0738 0.0616 1.0000 Uiso R . . . . . . H253 H -0.2299 0.6527 0.0475 0.0616 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(3) 0.059(3) 0.037(13) 0.018(5) 0.013(5) -0.008(3) C2 0.077(4) 0.051(3) 0.043(14) 0.001(5) -0.009(6) -0.019(3) C3 0.064(3) 0.039(3) 0.039(13) 0.003(5) 0.006(5) 0.004(3) C4 0.036(2) 0.026(2) 0.039(11) 0.000(3) 0.005(4) -0.0066(19) C5 0.028(2) 0.020(2) 0.040(9) -0.011(3) 0.006(3) -0.0078(17) C6 0.028(2) 0.023(2) 0.043(9) -0.008(4) 0.005(4) -0.0116(19) C7 0.021(2) 0.025(2) 0.043(8) -0.002(3) 0.008(3) -0.0082(17) C8 0.0247(19) 0.0172(19) 0.039(8) -0.007(3) 0.006(3) -0.0045(16) C9 0.024(2) 0.020(2) 0.038(10) -0.002(3) 0.005(3) -0.0049(17) C10 0.027(2) 0.023(2) 0.043(10) 0.002(4) 0.001(4) -0.0057(18) C11 0.036(2) 0.018(2) 0.046(10) -0.004(3) 0.001(4) -0.0013(18) C12 0.051(3) 0.015(2) 0.043(10) -0.002(3) 0.002(4) -0.006(2) C13 0.037(2) 0.022(2) 0.038(10) -0.007(3) 0.009(4) -0.0057(18) C14 0.0217(19) 0.023(2) 0.032(10) -0.008(3) 0.001(3) -0.0024(17) C15 0.041(2) 0.019(2) 0.029(10) -0.004(3) 0.006(4) -0.0081(19) C16 0.026(2) 0.020(2) 0.022(10) 0.002(3) 0.006(3) -0.0043(17) C17 0.041(2) 0.023(2) 0.067(14) -0.008(3) 0.004(4) -0.0077(19) C18 0.040(3) 0.032(2) 0.069(15) -0.005(4) 0.004(4) -0.005(2) C19 0.060(3) 0.021(2) 0.069(15) -0.015(4) 0.016(5) -0.009(2) C20 0.065(4) 0.048(3) 0.065(16) -0.015(5) -0.013(6) -0.012(3) C21 0.038(3) 0.053(3) 0.076(11) -0.007(5) -0.004(4) -0.008(2) C22 0.031(2) 0.032(2) 0.068(10) -0.005(4) -0.005(4) 0.000(2) C23 0.036(2) 0.033(2) 0.069(10) -0.014(4) -0.006(4) -0.014(2) C24 0.042(3) 0.047(3) 0.078(11) 0.006(4) -0.010(4) -0.024(2) C25 0.046(3) 0.051(3) 0.065(12) -0.005(5) -0.009(5) -0.011(3) N1 0.0337(19) 0.0228(18) 0.061(8) -0.007(3) -0.007(3) -0.0060(15) O1 0.0371(16) 0.0218(15) 0.041(8) 0.001(3) 0.002(3) -0.0070(13) O2 0.0356(16) 0.0173(15) 0.048(7) 0.003(2) -0.002(3) -0.0018(12) O3 0.0392(17) 0.0189(15) 0.041(11) 0.000(2) 0.005(3) -0.0070(13) O4 0.0444(18) 0.0165(15) 0.019(11) -0.002(2) 0.006(3) -0.0026(13) O5 0.050(2) 0.065(3) 0.081(11) 0.006(4) 0.009(3) -0.0305(19) Cu1 0.0357(5) 0.0162(5) 0.043(3) -0.0028(5) 0.0080(5) -0.0053(3) _refine_ls_extinction_coef 1400(400) _refine_ls_extinction_method 'Larson (1970), Equation 22' #_oxford_refine_ls_scale 1.668(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C4 . 1.573(9) yes C1 . H11 . 0.998 no C1 . H12 . 0.999 no C1 . H13 . 1.001 no C2 . C4 . 1.590(17) yes C2 . H21 . 0.996 no C2 . H22 . 0.991 no C2 . H23 . 1.000 no C3 . C4 . 1.549(9) yes C3 . H31 . 0.988 no C3 . H32 . 1.029 no C3 . H33 . 0.986 no C4 . C5 . 1.47(2) yes C5 . C6 . 1.394(16) yes C5 . O1 . 1.265(7) yes C6 . C7 . 1.35(2) yes C6 . H61 . 1.000 no C7 . C8 . 1.511(15) yes C7 . O2 . 1.309(9) yes C8 . C9 . 1.327(17) yes C8 . C13 . 1.414(7) yes C9 . C10 . 1.418(14) yes C9 . H91 . 1.001 no C10 . C11 . 1.409(7) yes C10 . C14 . 1.480(17) yes C11 . C12 . 1.341(17) yes C11 . H111 . 0.999 no C12 . C13 . 1.406(14) yes C12 . H121 . 1.000 no C13 . H131 . 1.007 no C14 . C15 . 1.380(15) yes C14 . O3 . 1.294(6) yes C15 . C16 . 1.394(19) yes C15 . H151 . 1.000 no C16 . C17 . 1.543(16) yes C16 . O4 . 1.275(6) yes C17 . C18 . 1.513(8) yes C17 . C19 . 1.537(8) yes C17 . C20 . 1.50(2) yes C18 . H181 . 1.003 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . H191 . 0.992 no C19 . H192 . 1.003 no C19 . H193 . 1.005 no C20 . H201 . 0.989 no C20 . H202 . 0.997 no C20 . H203 . 1.004 no C21 . C22 . 1.47(2) yes C21 . O5 . 1.438(9) yes C21 . H211 . 1.006 no C21 . H212 . 0.999 no C22 . N1 . 1.479(12) yes C22 . H221 . 0.995 no C22 . H222 . 1.006 no C23 . C24 . 1.45(2) yes C23 . N1 . 1.483(7) yes C23 . H231 . 0.999 no C23 . H232 . 1.002 no C24 . O5 . 1.398(13) yes C24 . H241 . 0.996 no C24 . H242 . 1.001 no C25 . N1 . 1.43(2) yes C25 . H251 . 0.992 no C25 . H252 . 1.002 no C25 . H253 . 0.991 no N1 . Cu1 . 2.445(7) yes O1 . Cu1 . 1.915(8) yes O2 . Cu1 . 1.924(6) yes O3 . Cu1 2_665 1.917(7) yes O4 . Cu1 2_665 1.942(6) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 . C1 . H11 . 109.8 no C4 . C1 . H12 . 109.0 no H11 . C1 . H12 . 109.7 no C4 . C1 . H13 . 109.3 no H11 . C1 . H13 . 109.5 no H12 . C1 . H13 . 109.5 no C4 . C2 . H21 . 108.3 no C4 . C2 . H22 . 109.7 no H21 . C2 . H22 . 110.5 no C4 . C2 . H23 . 108.2 no H21 . C2 . H23 . 109.8 no H22 . C2 . H23 . 110.2 no C4 . C3 . H31 . 110.4 no C4 . C3 . H32 . 108.1 no H31 . C3 . H32 . 108.1 no C4 . C3 . H33 . 110.2 no H31 . C3 . H33 . 111.7 no H32 . C3 . H33 . 108.3 no C3 . C4 . C1 . 107.6(6) yes C3 . C4 . C2 . 105.0(10) yes C1 . C4 . C2 . 105.1(10) yes C3 . C4 . C5 . 117.7(10) yes C1 . C4 . C5 . 111.1(9) yes C2 . C4 . C5 . 109.4(7) yes C4 . C5 . C6 . 121.5(6) yes C4 . C5 . O1 . 114.6(10) yes C6 . C5 . O1 . 123.8(12) yes C5 . C6 . C7 . 125.7(7) yes C5 . C6 . H61 . 117.2 no C7 . C6 . H61 . 117.1 no C6 . C7 . C8 . 123.3(6) yes C6 . C7 . O2 . 125.5(10) yes C8 . C7 . O2 . 111.2(11) yes C7 . C8 . C9 . 121.0(5) yes C7 . C8 . C13 . 118.8(10) yes C9 . C8 . C13 . 120.1(9) yes C8 . C9 . C10 . 122.7(5) yes C8 . C9 . H91 . 118.8 no C10 . C9 . H91 . 118.4 no C9 . C10 . C11 . 116.5(10) yes C9 . C10 . C14 . 119.7(5) yes C11 . C10 . C14 . 123.8(9) yes C10 . C11 . C12 . 121.2(9) yes C10 . C11 . H111 . 119.7 no C12 . C11 . H111 . 119.1 no C11 . C12 . C13 . 121.3(5) yes C11 . C12 . H121 . 119.5 no C13 . C12 . H121 . 119.2 no C8 . C13 . C12 . 118.0(10) yes C8 . C13 . H131 . 121.0 no C12 . C13 . H131 . 121.0 no C10 . C14 . C15 . 121.4(5) yes C10 . C14 . O3 . 115.4(9) yes C15 . C14 . O3 . 123.2(10) yes C14 . C15 . C16 . 125.6(5) yes C14 . C15 . H151 . 117.4 no C16 . C15 . H151 . 117.0 no C15 . C16 . C17 . 123.5(5) yes C15 . C16 . O4 . 124.3(9) yes C17 . C16 . O4 . 112.1(10) yes C16 . C17 . C18 . 106.7(7) yes C16 . C17 . C19 . 113.1(10) yes C18 . C17 . C19 . 107.3(5) yes C16 . C17 . C20 . 108.9(6) yes C18 . C17 . C20 . 111.0(11) yes C19 . C17 . C20 . 109.8(7) yes C17 . C18 . H181 . 109.6 no C17 . C18 . H182 . 109.5 no H181 . C18 . H182 . 109.2 no C17 . C18 . H183 . 109.8 no H181 . C18 . H183 . 109.2 no H182 . C18 . H183 . 109.5 no C17 . C19 . H191 . 109.8 no C17 . C19 . H192 . 109.6 no H191 . C19 . H192 . 109.9 no C17 . C19 . H193 . 109.0 no H191 . C19 . H193 . 109.7 no H192 . C19 . H193 . 108.8 no C17 . C20 . H201 . 109.4 no C17 . C20 . H202 . 108.8 no H201 . C20 . H202 . 110.7 no C17 . C20 . H203 . 108.4 no H201 . C20 . H203 . 110.1 no H202 . C20 . H203 . 109.4 no C22 . C21 . O5 . 111.4(13) yes C22 . C21 . H211 . 109.0 no O5 . C21 . H211 . 108.7 no C22 . C21 . H212 . 109.5 no O5 . C21 . H212 . 109.1 no H211 . C21 . H212 . 109.0 no C21 . C22 . N1 . 111.0(6) yes C21 . C22 . H221 . 109.3 no N1 . C22 . H221 . 108.7 no C21 . C22 . H222 . 109.5 no N1 . C22 . H222 . 108.9 no H221 . C22 . H222 . 109.4 no C24 . C23 . N1 . 112.3(11) yes C24 . C23 . H231 . 108.8 no N1 . C23 . H231 . 109.1 no C24 . C23 . H232 . 108.8 no N1 . C23 . H232 . 108.4 no H231 . C23 . H232 . 109.4 no C23 . C24 . O5 . 112.4(7) yes C23 . C24 . H241 . 108.0 no O5 . C24 . H241 . 108.7 no C23 . C24 . H242 . 108.4 no O5 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.7 no N1 . C25 . H251 . 108.8 no N1 . C25 . H252 . 108.1 no H251 . C25 . H252 . 110.0 no N1 . C25 . H253 . 109.1 no H251 . C25 . H253 . 110.9 no H252 . C25 . H253 . 110.0 no C23 . N1 . C22 . 108.2(6) yes C23 . N1 . C25 . 109.4(11) yes C22 . N1 . C25 . 109.1(7) yes C23 . N1 . Cu1 . 114.5(4) yes C22 . N1 . Cu1 . 110.1(7) yes C25 . N1 . Cu1 . 105.5(4) yes C5 . O1 . Cu1 . 125.9(8) yes C7 . O2 . Cu1 . 123.9(9) yes C14 . O3 . Cu1 2_665 127.7(7) yes C16 . O4 . Cu1 2_665 126.7(8) yes C21 . O5 . C24 . 109.5(5) yes N1 . Cu1 . O4 2_665 97.2(2) yes N1 . Cu1 . O2 . 89.2(2) yes O4 2_665 Cu1 . O2 . 173.6(2) yes N1 . Cu1 . O3 2_665 91.3(3) yes O4 2_665 Cu1 . O3 2_665 91.5(3) yes O2 . Cu1 . O3 2_665 88.3(3) yes N1 . Cu1 . O1 . 100.9(3) yes O4 2_665 Cu1 . O1 . 85.8(3) yes O2 . Cu1 . O1 . 93.0(3) yes O3 2_665 Cu1 . O1 . 167.7(2) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C21 . H212 . O1 . 142 1.00 2.58 3.428(12) yes C22 . H222 . O3 2_565 161 1.01 2.46 3.427(12) yes C24 . H241 . O1 . 148 1.00 2.48 3.362(12) yes C25 . H252 . C14 2_665 133 1.00 2.59 3.358(12) yes # Attachment 'Fig_10.CIF' data_lj131sad _database_code_depnum_ccdc_archive 'CCDC 754704' #TrackingRef 'Fig_10.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C22 H29 Cu N O4, C2 H5 N, C4 H8 O ' _chemical_formula_sum 'C28 H42 Cu N2 O5' _chemical_formula_weight 550.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall '-p 1' #_symmetry_international_tables_no '2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.340(5) _cell_length_b 11.737(6) _cell_length_c 12.916(6) _cell_angle_alpha 95.039(8) _cell_angle_beta 113.367(7) _cell_angle_gamma 98.987(8) _cell_volume 1401.8(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3411 _cell_measurement_theta_min 2.155 _cell_measurement_theta_max 26.095 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 0.818 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14064 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.49 _reflns_number_total 6574 _reflns_number_gt 4826 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0742P)^2^+0.5502P] 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 6574 _refine_ls_number_parameters 334 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.3440(5) -0.0345(3) 0.6902(4) 0.0552(11) Uani 1 1 d . . . H1A H -0.2443 -0.0426 0.7106 0.083 Uiso 1 1 calc R . . H1B H -0.3983 -0.0534 0.6069 0.083 Uiso 1 1 calc R . . H1C H -0.3884 -0.0882 0.7265 0.083 Uiso 1 1 calc R . . C2 C -0.5022(4) 0.0999(4) 0.6976(4) 0.0479(10) Uani 1 1 d . . . H2A H -0.5456 0.0459 0.7343 0.072 Uiso 1 1 calc R . . H2B H -0.5555 0.0795 0.6144 0.072 Uiso 1 1 calc R . . H2C H -0.5062 0.1801 0.7225 0.072 Uiso 1 1 calc R . . C3 C -0.2629(5) 0.1228(5) 0.8597(3) 0.0666(14) Uani 1 1 d . . . H3A H -0.3098 0.0724 0.8969 0.100 Uiso 1 1 calc R . . H3B H -0.2614 0.2047 0.8837 0.100 Uiso 1 1 calc R . . H3C H -0.1639 0.1120 0.8816 0.100 Uiso 1 1 calc R . . C4 C -0.3455(3) 0.0908(3) 0.7313(3) 0.0304(7) Uani 1 1 d . . . C5 C -0.2676(3) 0.1717(2) 0.6771(2) 0.0231(6) Uani 1 1 d . . . C6 C -0.3407(3) 0.2380(3) 0.5976(3) 0.0262(6) Uani 1 1 d . . . H6 H -0.4403 0.2328 0.5786 0.031 Uiso 1 1 calc R . . C7 C -0.2768(3) 0.3117(2) 0.5441(2) 0.0215(6) Uani 1 1 d . . . C8 C -0.3654(3) 0.3771(2) 0.4570(2) 0.0216(6) Uani 1 1 d . . . C9 C -0.2944(3) 0.4563(2) 0.4131(2) 0.0212(6) Uani 1 1 d . . . H9 H -0.1929 0.4666 0.4393 0.025 Uiso 1 1 calc R . . C10 C -0.3677(3) 0.5210(2) 0.3321(2) 0.0222(6) Uani 1 1 d . . . C11 C -0.5171(3) 0.5077(3) 0.2962(3) 0.0266(6) Uani 1 1 d . . . H11 H -0.5688 0.5525 0.2424 0.032 Uiso 1 1 calc R . . C12 C -0.5882(3) 0.4297(3) 0.3392(3) 0.0286(7) Uani 1 1 d . . . H12 H -0.6894 0.4210 0.3144 0.034 Uiso 1 1 calc R . . C13 C -0.5154(3) 0.3639(3) 0.4178(3) 0.0262(6) Uani 1 1 d . . . H13 H -0.5669 0.3094 0.4454 0.031 Uiso 1 1 calc R . . C14 C -0.2819(3) 0.6027(2) 0.2882(2) 0.0213(6) Uani 1 1 d . . . C15 C -0.3516(3) 0.6441(3) 0.1863(3) 0.0268(6) Uani 1 1 d . . . H15 H -0.4533 0.6197 0.1472 0.032 Uiso 1 1 calc R . . C16 C -0.2799(3) 0.7193(3) 0.1389(2) 0.0249(6) Uani 1 1 d . . . C17 C -0.3614(3) 0.7559(3) 0.0233(3) 0.0303(7) Uani 1 1 d . . . C18 C -0.3634(5) 0.8857(3) 0.0462(3) 0.0537(11) Uani 1 1 d . . . H18A H -0.4121 0.8970 0.0966 0.080 Uiso 1 1 calc R . . H18B H -0.4151 0.9117 -0.0263 0.080 Uiso 1 1 calc R . . H18C H -0.2643 0.9313 0.0830 0.080 Uiso 1 1 calc R . . C19 C -0.2783(5) 0.7407(5) -0.0495(3) 0.0635(13) Uani 1 1 d . . . H19A H -0.1842 0.7945 -0.0138 0.095 Uiso 1 1 calc R . . H19B H -0.3326 0.7576 -0.1260 0.095 Uiso 1 1 calc R . . H19C H -0.2646 0.6600 -0.0557 0.095 Uiso 1 1 calc R . . C20 C -0.5159(4) 0.6875(4) -0.0407(3) 0.0580(12) Uani 1 1 d . . . H20A H -0.5167 0.6036 -0.0489 0.087 Uiso 1 1 calc R . . H20B H -0.5583 0.7097 -0.1166 0.087 Uiso 1 1 calc R . . H20C H -0.5720 0.7052 0.0022 0.087 Uiso 1 1 calc R . . C21 C -0.1281(3) 0.0414(3) 0.4799(3) 0.0423(9) Uani 1 1 d . . . H21A H -0.1986 0.0865 0.4358 0.051 Uiso 1 1 calc R . . H21B H -0.1634 0.0062 0.5332 0.051 Uiso 1 1 calc R . . C22 C -0.1208(3) -0.0557(3) 0.3980(3) 0.0383(8) Uani 1 1 d . . . H22A H -0.2158 -0.1102 0.3611 0.046 Uiso 1 1 calc R . . H22B H -0.1008 -0.0213 0.3373 0.046 Uiso 1 1 calc R . . C1T C -0.1350(4) 0.3015(4) 0.2715(4) 0.0552(11) Uani 1 1 d . . . H1T1 H -0.1668 0.3671 0.2316 0.066 Uiso 1 1 calc R . . H1T2 H -0.1977 0.2769 0.3103 0.066 Uiso 1 1 calc R . . C2T C 0.0197(4) 0.3360(4) 0.3551(3) 0.0486(10) Uani 1 1 d . . . H2T1 H 0.0715 0.4007 0.3328 0.058 Uiso 1 1 calc R . . H2T2 H 0.0277 0.3616 0.4329 0.058 Uiso 1 1 calc R . . O1T O 0.0776(3) 0.2336(3) 0.3516(3) 0.0625(8) Uani 1 1 d . . . C3T C 0.0110(6) 0.1813(5) 0.2334(4) 0.0685(14) Uani 1 1 d . . . H3T1 H 0.0107 0.0966 0.2252 0.082 Uiso 1 1 calc R . . H3T2 H 0.0633 0.2184 0.1913 0.082 Uiso 1 1 calc R . . C4T C -0.1383(5) 0.2006(5) 0.1889(4) 0.0778(16) Uani 1 1 d . . . H4T1 H -0.2063 0.1298 0.1864 0.093 Uiso 1 1 calc R . . H4T2 H -0.1680 0.2203 0.1109 0.093 Uiso 1 1 calc R . . C23 C 0.0647(8) 0.5519(7) 0.1115(4) 0.128(3) Uani 1 1 d D . . H23A H 0.0590 0.6351 0.1239 0.153 Uiso 1 1 calc R . . H23B H 0.1101 0.5306 0.1884 0.153 Uiso 1 1 calc R . . C24 C -0.0877(8) 0.4838(9) 0.0595(6) 0.189(5) Uani 1 1 d D . . H24A H -0.0877 0.4106 0.0921 0.226 Uiso 1 1 calc R . . H24B H -0.1441 0.5293 0.0869 0.226 Uiso 1 1 calc R . . N2 N -0.1659(9) 0.4518(6) -0.0621(7) 0.160(3) Uani 1 1 d D . . N1 N 0.0105(3) 0.1214(2) 0.5462(2) 0.0280(6) Uani 1 1 d D . . H1N H 0.044(4) 0.153(3) 0.499(2) 0.042 Uiso 1 1 d D . . O1 O -0.1349(2) 0.16978(19) 0.71088(18) 0.0297(5) Uani 1 1 d . . . O2 O -0.1444(2) 0.32869(18) 0.56267(18) 0.0266(5) Uani 1 1 d . . . O3 O -0.1468(2) 0.62552(18) 0.34849(17) 0.0255(4) Uani 1 1 d . . . O4 O -0.1469(2) 0.76494(19) 0.18594(18) 0.0289(5) Uani 1 1 d . . . Cu1 Cu 0.00404(4) 0.26409(3) 0.67301(3) 0.02317(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.066(3) 0.033(2) 0.084(3) 0.022(2) 0.048(3) 0.0083(19) C2 0.041(2) 0.056(2) 0.061(3) 0.032(2) 0.0312(19) 0.0100(18) C3 0.058(3) 0.096(4) 0.031(2) 0.017(2) 0.0167(19) -0.024(2) C4 0.0276(16) 0.0341(17) 0.0307(17) 0.0122(14) 0.0137(14) 0.0014(13) C5 0.0254(15) 0.0231(15) 0.0218(14) 0.0040(12) 0.0119(12) 0.0022(11) C6 0.0223(14) 0.0300(16) 0.0282(16) 0.0079(13) 0.0121(13) 0.0044(12) C7 0.0212(14) 0.0196(14) 0.0219(14) 0.0002(11) 0.0076(11) 0.0043(11) C8 0.0194(13) 0.0216(14) 0.0234(15) 0.0009(12) 0.0092(12) 0.0038(11) C9 0.0181(13) 0.0231(14) 0.0199(14) 0.0018(11) 0.0056(11) 0.0043(11) C10 0.0198(13) 0.0231(14) 0.0220(14) 0.0027(12) 0.0070(11) 0.0048(11) C11 0.0207(14) 0.0311(16) 0.0242(15) 0.0059(13) 0.0038(12) 0.0095(12) C12 0.0166(13) 0.0367(18) 0.0291(16) 0.0050(14) 0.0064(12) 0.0051(12) C13 0.0233(14) 0.0269(16) 0.0277(16) 0.0061(13) 0.0108(13) 0.0020(12) C14 0.0209(13) 0.0192(14) 0.0216(14) 0.0024(11) 0.0063(11) 0.0055(11) C15 0.0228(14) 0.0261(16) 0.0240(15) 0.0052(12) 0.0020(12) 0.0046(12) C16 0.0290(15) 0.0244(15) 0.0203(14) 0.0049(12) 0.0075(12) 0.0097(12) C17 0.0325(16) 0.0330(17) 0.0217(15) 0.0088(13) 0.0063(13) 0.0075(13) C18 0.075(3) 0.042(2) 0.041(2) 0.0202(18) 0.014(2) 0.024(2) C19 0.069(3) 0.104(4) 0.027(2) 0.021(2) 0.020(2) 0.038(3) C20 0.049(2) 0.061(3) 0.034(2) 0.0229(19) -0.0098(18) -0.005(2) C21 0.0234(16) 0.041(2) 0.050(2) -0.0110(17) 0.0045(15) 0.0096(14) C22 0.0246(16) 0.0392(19) 0.0374(19) -0.0074(15) 0.0000(14) 0.0113(14) C1T 0.048(2) 0.061(3) 0.050(2) -0.008(2) 0.017(2) 0.009(2) C2T 0.050(2) 0.049(2) 0.035(2) 0.0078(18) 0.0097(18) 0.0006(18) O1T 0.0533(18) 0.080(2) 0.0570(19) 0.0246(17) 0.0194(15) 0.0253(16) C3T 0.089(4) 0.082(3) 0.060(3) 0.017(3) 0.046(3) 0.045(3) C4T 0.073(3) 0.080(4) 0.055(3) -0.018(3) 0.000(2) 0.030(3) C23 0.128(6) 0.144(7) 0.125(6) 0.009(5) 0.085(6) -0.014(5) C24 0.242(13) 0.172(10) 0.089(6) 0.052(6) 0.000(7) 0.038(9) N2 0.203(8) 0.126(6) 0.170(8) 0.041(6) 0.079(7) 0.072(6) N1 0.0279(13) 0.0271(14) 0.0270(14) 0.0051(11) 0.0099(11) 0.0045(11) O1 0.0257(11) 0.0335(12) 0.0327(12) 0.0163(10) 0.0125(9) 0.0069(9) O2 0.0196(10) 0.0308(11) 0.0319(12) 0.0143(9) 0.0109(9) 0.0060(8) O3 0.0195(10) 0.0299(11) 0.0244(10) 0.0123(9) 0.0048(8) 0.0050(8) O4 0.0259(11) 0.0318(12) 0.0253(11) 0.0102(9) 0.0069(9) 0.0024(9) Cu1 0.01918(19) 0.0262(2) 0.0235(2) 0.00951(14) 0.00724(14) 0.00448(13) _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 C4 1.524(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.526(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.513(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.538(4) . ? C5 O1 1.269(3) . ? C5 C6 1.392(4) . ? C6 C7 1.397(4) . ? C6 H6 0.9500 . ? C7 O2 1.272(3) . ? C7 C8 1.499(4) . ? C8 C9 1.391(4) . ? C8 C13 1.404(4) . ? C9 C10 1.392(4) . ? C9 H9 0.9500 . ? C10 C11 1.403(4) . ? C10 C14 1.502(4) . ? C11 C12 1.375(4) . ? C11 H11 0.9500 . ? C12 C13 1.382(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.270(3) . ? C14 C15 1.398(4) . ? C15 C16 1.398(4) . ? C15 H15 0.9500 . ? C16 O4 1.264(4) . ? C16 C17 1.534(4) . ? C17 C19 1.521(5) . ? C17 C20 1.521(5) . ? C17 C18 1.530(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N1 1.460(4) . ? C21 C22 1.517(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N1 1.462(4) 2_556 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C1T C2T 1.496(5) . ? C1T C4T 1.510(6) . ? C1T H1T1 0.9900 . ? C1T H1T2 0.9900 . ? C2T O1T 1.429(5) . ? C2T H2T1 0.9900 . ? C2T H2T2 0.9900 . ? O1T C3T 1.433(6) . ? C3T C4T 1.481(6) . ? C3T H3T1 0.9900 . ? C3T H3T2 0.9900 . ? C4T H4T1 0.9900 . ? C4T H4T2 0.9900 . ? C23 N2 1.430(9) 2_565 ? C23 C24 1.498(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N2 1.433(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? N2 C23 1.430(9) 2_565 ? N1 C22 1.462(4) 2_556 ? N1 Cu1 2.265(3) . ? N1 H1N 0.89(4) . ? O1 Cu1 1.919(2) . ? O2 Cu1 1.944(2) . ? O3 Cu1 1.930(2) 2_566 ? O4 Cu1 1.936(2) 2_566 ? Cu1 O3 1.930(2) 2_566 ? Cu1 O4 1.936(2) 2_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 C4 C1 110.9(4) . . ? C3 C4 C2 109.6(3) . . ? C1 C4 C2 107.9(3) . . ? C3 C4 C5 107.4(3) . . ? C1 C4 C5 107.4(3) . . ? C2 C4 C5 113.6(3) . . ? O1 C5 C6 125.1(3) . . ? O1 C5 C4 113.6(3) . . ? C6 C5 C4 121.4(3) . . ? C5 C6 C7 124.1(3) . . ? C5 C6 H6 117.9 . . ? C7 C6 H6 117.9 . . ? O2 C7 C6 124.7(3) . . ? O2 C7 C8 115.0(2) . . ? C6 C7 C8 120.3(2) . . ? C9 C8 C13 118.1(3) . . ? C9 C8 C7 117.9(2) . . ? C13 C8 C7 124.0(3) . . ? C8 C9 C10 121.9(3) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C11 118.7(3) . . ? C9 C10 C14 118.0(2) . . ? C11 C10 C14 123.3(3) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 121.2(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 120.2(3) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O3 C14 C15 125.3(3) . . ? O3 C14 C10 114.7(2) . . ? C15 C14 C10 120.0(2) . . ? C16 C15 C14 123.7(3) . . ? C16 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? O4 C16 C15 124.7(3) . . ? O4 C16 C17 114.1(3) . . ? C15 C16 C17 121.2(3) . . ? C19 C17 C20 109.7(3) . . ? C19 C17 C18 108.9(3) . . ? C20 C17 C18 108.7(3) . . ? C19 C17 C16 108.2(3) . . ? C20 C17 C16 113.7(3) . . ? C18 C17 C16 107.5(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N1 C21 C22 113.2(3) . . ? N1 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? N1 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? N1 C22 C21 113.2(3) 2_556 . ? N1 C22 H22A 108.9 2_556 . ? C21 C22 H22A 108.9 . . ? N1 C22 H22B 108.9 2_556 . ? C21 C22 H22B 108.9 . . ? H22A C22 H22B 107.8 . . ? C2T C1T C4T 104.0(3) . . ? C2T C1T H1T1 111.0 . . ? C4T C1T H1T1 111.0 . . ? C2T C1T H1T2 111.0 . . ? C4T C1T H1T2 111.0 . . ? H1T1 C1T H1T2 109.0 . . ? O1T C2T C1T 105.6(3) . . ? O1T C2T H2T1 110.6 . . ? C1T C2T H2T1 110.6 . . ? O1T C2T H2T2 110.6 . . ? C1T C2T H2T2 110.6 . . ? H2T1 C2T H2T2 108.8 . . ? C2T O1T C3T 104.4(3) . . ? O1T C3T C4T 106.0(3) . . ? O1T C3T H3T1 110.5 . . ? C4T C3T H3T1 110.5 . . ? O1T C3T H3T2 110.5 . . ? C4T C3T H3T2 110.5 . . ? H3T1 C3T H3T2 108.7 . . ? C3T C4T C1T 105.2(4) . . ? C3T C4T H4T1 110.7 . . ? C1T C4T H4T1 110.7 . . ? C3T C4T H4T2 110.7 . . ? C1T C4T H4T2 110.7 . . ? H4T1 C4T H4T2 108.8 . . ? N2 C23 C24 125.1(5) 2_565 . ? N2 C23 H23A 106.0 2_565 . ? C24 C23 H23A 106.0 . . ? N2 C23 H23B 106.0 2_565 . ? C24 C23 H23B 106.0 . . ? H23A C23 H23B 106.3 . . ? N2 C24 C23 121.1(5) . . ? N2 C24 H24A 107.1 . . ? C23 C24 H24A 107.1 . . ? N2 C24 H24B 107.1 . . ? C23 C24 H24B 107.1 . . ? H24A C24 H24B 106.8 . . ? C23 N2 C24 108.4(6) 2_565 . ? C21 N1 C22 110.1(3) . 2_556 ? C21 N1 Cu1 113.9(2) . . ? C22 N1 Cu1 111.46(19) 2_556 . ? C21 N1 H1N 110(2) . . ? C22 N1 H1N 101(2) 2_556 . ? Cu1 N1 H1N 110(2) . . ? C5 O1 Cu1 127.25(19) . . ? C7 O2 Cu1 126.69(19) . . ? C14 O3 Cu1 126.68(19) . 2_566 ? C16 O4 Cu1 127.44(19) . 2_566 ? O1 Cu1 O3 172.35(10) . 2_566 ? O1 Cu1 O4 85.85(9) . 2_566 ? O3 Cu1 O4 91.65(9) 2_566 2_566 ? O1 Cu1 O2 91.73(9) . . ? O3 Cu1 O2 88.55(9) 2_566 . ? O4 Cu1 O2 162.93(9) 2_566 . ? O1 Cu1 N1 95.83(10) . . ? O3 Cu1 N1 91.73(10) 2_566 . ? O4 Cu1 N1 100.44(10) 2_566 . ? O2 Cu1 N1 96.62(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C4 C5 O1 54.3(4) . . . . ? C1 C4 C5 O1 -65.1(4) . . . . ? C2 C4 C5 O1 175.7(3) . . . . ? C3 C4 C5 C6 -126.5(4) . . . . ? C1 C4 C5 C6 114.1(3) . . . . ? C2 C4 C5 C6 -5.2(4) . . . . ? O1 C5 C6 C7 0.1(5) . . . . ? C4 C5 C6 C7 -178.9(3) . . . . ? C5 C6 C7 O2 -1.3(5) . . . . ? C5 C6 C7 C8 178.3(3) . . . . ? O2 C7 C8 C9 -5.5(4) . . . . ? C6 C7 C8 C9 174.9(3) . . . . ? O2 C7 C8 C13 175.0(3) . . . . ? C6 C7 C8 C13 -4.6(4) . . . . ? C13 C8 C9 C10 -0.5(4) . . . . ? C7 C8 C9 C10 -180.0(3) . . . . ? C8 C9 C10 C11 1.8(4) . . . . ? C8 C9 C10 C14 -178.9(3) . . . . ? C9 C10 C11 C12 -1.6(4) . . . . ? C14 C10 C11 C12 179.0(3) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C8 1.1(5) . . . . ? C9 C8 C13 C12 -1.0(4) . . . . ? C7 C8 C13 C12 178.5(3) . . . . ? C9 C10 C14 O3 -15.9(4) . . . . ? C11 C10 C14 O3 163.5(3) . . . . ? C9 C10 C14 C15 162.1(3) . . . . ? C11 C10 C14 C15 -18.6(4) . . . . ? O3 C14 C15 C16 -1.6(5) . . . . ? C10 C14 C15 C16 -179.4(3) . . . . ? C14 C15 C16 O4 -5.2(5) . . . . ? C14 C15 C16 C17 176.4(3) . . . . ? O4 C16 C17 C19 49.3(4) . . . . ? C15 C16 C17 C19 -132.2(3) . . . . ? O4 C16 C17 C20 171.5(3) . . . . ? C15 C16 C17 C20 -9.9(4) . . . . ? O4 C16 C17 C18 -68.1(4) . . . . ? C15 C16 C17 C18 110.4(3) . . . . ? N1 C21 C22 N1 53.7(5) . . . 2_556 ? C4T C1T C2T O1T -24.8(5) . . . . ? C1T C2T O1T C3T 38.3(4) . . . . ? C2T O1T C3T C4T -36.7(5) . . . . ? O1T C3T C4T C1T 20.6(6) . . . . ? C2T C1T C4T C3T 2.5(6) . . . . ? N2 C23 C24 N2 -29.0(16) 2_565 . . . ? C23 C24 N2 C23 24.7(14) . . . 2_565 ? C22 C21 N1 C22 -52.2(5) . . . 2_556 ? C22 C21 N1 Cu1 -178.3(2) . . . . ? C6 C5 O1 Cu1 5.3(4) . . . . ? C4 C5 O1 Cu1 -175.65(19) . . . . ? C6 C7 O2 Cu1 -2.9(4) . . . . ? C8 C7 O2 Cu1 177.52(18) . . . . ? C15 C14 O3 Cu1 7.7(4) . . . 2_566 ? C10 C14 O3 Cu1 -174.48(17) . . . 2_566 ? C15 C16 O4 Cu1 5.2(4) . . . 2_566 ? C17 C16 O4 Cu1 -176.36(19) . . . 2_566 ? C5 O1 Cu1 O4 156.2(3) . . . 2_566 ? C5 O1 Cu1 O2 -6.9(3) . . . . ? C5 O1 Cu1 N1 -103.7(3) . . . . ? C7 O2 Cu1 O1 5.7(2) . . . . ? C7 O2 Cu1 O3 -166.7(2) . . . 2_566 ? C7 O2 Cu1 O4 -75.8(4) . . . 2_566 ? C7 O2 Cu1 N1 101.8(2) . . . . ? C21 N1 Cu1 O1 35.2(2) . . . . ? C22 N1 Cu1 O1 -90.3(2) 2_556 . . . ? C21 N1 Cu1 O3 -146.0(2) . . . 2_566 ? C22 N1 Cu1 O3 88.6(2) 2_556 . . 2_566 ? C21 N1 Cu1 O4 122.0(2) . . . 2_566 ? C22 N1 Cu1 O4 -3.4(2) 2_556 . . 2_566 ? C21 N1 Cu1 O2 -57.3(2) . . . . ? C22 N1 Cu1 O2 177.3(2) 2_556 . . . ? 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 H1N O1T 0.89(4) 2.32(3) 3.195(4) 167(3) . _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.798 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.084 # Attachment 'Fig_1_Cupy1.CIF' data_lfl119sad _database_code_depnum_ccdc_archive 'CCDC 754705' #TrackingRef 'Fig_1_Cupy1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H34 Cu2 N2 O8, C5 H5 N1' _chemical_formula_sum 'C43 H39 Cu2 N3 O8' _chemical_formula_weight 852.85 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2980(6) _cell_length_b 8.7950(7) _cell_length_c 14.0240(11) _cell_angle_alpha 76.427(4) _cell_angle_beta 85.101(4) _cell_angle_gamma 72.381(4) _cell_volume 948.12(13) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6425 _cell_measurement_theta_min 2.6075 _cell_measurement_theta_max 29.2655 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.208 _exptl_crystal_size_mid 0.171 _exptl_crystal_size_min 0.081 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 1.181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.712 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_process_details 'SADABS, (Sheldrick, 2003)' _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17585 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5703 _reflns_number_gt 4670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius,2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius,2003)' _computing_data_reduction 'SAINT and XPREP (Bruker-Nonius 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0443P)^2^+0.4330P] 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 5703 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.86072(3) 0.22400(2) 0.739346(14) 0.02465(7) Uani 1 1 d . . . N1 N 1.09913(19) 0.27991(19) 0.67289(11) 0.0282(3) Uani 1 1 d . . . O1 O 0.70834(16) 0.43534(16) 0.68449(9) 0.0310(3) Uani 1 1 d . . . O2 O 0.86888(17) 0.27900(15) 0.86390(9) 0.0286(3) Uani 1 1 d . . . O3 O 1.02469(17) -0.00291(15) 1.19422(9) 0.0290(3) Uani 1 1 d . . . O4 O 1.18866(16) -0.15183(16) 1.37322(9) 0.0300(3) Uani 1 1 d . . . C1 C 0.5127(3) 0.6941(3) 0.67544(18) 0.0503(6) Uani 1 1 d . . . H1A H 0.4148 0.6650 0.6636 0.060 Uiso 1 1 calc R . . H1C H 0.5619 0.7345 0.6139 0.060 Uiso 1 1 calc R . . H1B H 0.4803 0.7773 0.7129 0.060 Uiso 1 1 calc R . . C2 C 0.6400(3) 0.5456(2) 0.73171(14) 0.0337(4) Uani 1 1 d . . . C3 C 0.6704(3) 0.5399(2) 0.82827(15) 0.0423(5) Uani 1 1 d . . . H3 H 0.6110 0.6292 0.8545 0.051 Uiso 1 1 calc R . . C4 C 0.7841(2) 0.4096(2) 0.88907(13) 0.0288(3) Uani 1 1 d . . . C5 C 0.8094(2) 0.4182(2) 0.99153(13) 0.0306(4) Uani 1 1 d . . . C6 C 0.8966(2) 0.2786(2) 1.05717(12) 0.0266(3) Uani 1 1 d . . . H6 H 0.9385 0.1807 1.0365 0.032 Uiso 1 1 calc R . . C7 C 0.9228(2) 0.2819(2) 1.15308(13) 0.0286(3) Uani 1 1 d . . . C8 C 0.8613(3) 0.4301(2) 1.18280(16) 0.0467(6) Uani 1 1 d . . . H8 H 0.8778 0.4348 1.2467 0.056 Uiso 1 1 calc R . . C9 C 0.7763(4) 0.5688(3) 1.11780(18) 0.0624(8) Uani 1 1 d . . . H9 H 0.7363 0.6672 1.1380 0.075 Uiso 1 1 calc R . . C10 C 0.7496(4) 0.5641(2) 1.02359(17) 0.0505(6) Uani 1 1 d . . . H10 H 0.6912 0.6592 0.9807 0.061 Uiso 1 1 calc R . . C11 C 1.0126(2) 0.1278(2) 1.22208(12) 0.0262(3) Uani 1 1 d . . . C12 C 1.0777(3) 0.1330(2) 1.30957(14) 0.0338(4) Uani 1 1 d . . . H12 H 1.0669 0.2352 1.3217 0.041 Uiso 1 1 calc R . . C13 C 1.1578(2) -0.0045(2) 1.37978(13) 0.0300(4) Uani 1 1 d . . . C14 C 1.2164(3) 0.0192(3) 1.47303(15) 0.0408(5) Uani 1 1 d . . . H14B H 1.3377 -0.0171 1.4746 0.049 Uiso 1 1 calc R . . H14C H 1.1718 -0.0431 1.5288 0.049 Uiso 1 1 calc R . . H14A H 1.1770 0.1330 1.4749 0.049 Uiso 1 1 calc R . . C15 C 1.2499(2) 0.1748(3) 0.69901(15) 0.0381(4) Uani 1 1 d . . . H15 H 1.2539 0.0767 0.7433 0.046 Uiso 1 1 calc R . . C16 C 1.3999(3) 0.2041(3) 0.66377(17) 0.0464(5) Uani 1 1 d . . . H16 H 1.5027 0.1282 0.6846 0.056 Uiso 1 1 calc R . . C17 C 1.3955(3) 0.3474(3) 0.59729(16) 0.0451(5) Uani 1 1 d . . . H17 H 1.4952 0.3701 0.5724 0.054 Uiso 1 1 calc R . . C18 C 1.2408(3) 0.4570(3) 0.56808(15) 0.0397(5) Uani 1 1 d . . . H18 H 1.2338 0.5543 0.5224 0.048 Uiso 1 1 calc R . . C19 C 1.0962(2) 0.4185(2) 0.60849(13) 0.0311(4) Uani 1 1 d . . . H19 H 0.9918 0.4932 0.5897 0.037 Uiso 1 1 calc R . . C20 C 0.5646(4) -0.0174(3) 0.9095(2) 0.0630(8) Uani 1 1 d . . . H20 H 0.6089 -0.0294 0.8476 0.076 Uiso 1 1 calc R A 1 C21 C 0.5843(4) 0.0427(3) 1.0618(3) 0.0673(8) Uani 1 1 d . . . H21 H 0.6444 0.0722 1.1039 0.081 Uiso 1 1 calc R B 1 N20 N 0.6493(3) 0.0253(3) 0.9704(3) 0.0718(9) Uani 0.50 1 d P C 1 C22 C 0.6493(3) 0.0253(3) 0.9704(3) 0.0718(9) Uani 0.50 1 d P C 2 H22 H 0.7531 0.0433 0.9508 0.086 Uiso 0.50 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02552(11) 0.02446(11) 0.02207(11) -0.00441(7) -0.00254(7) -0.00445(8) N1 0.0263(7) 0.0348(8) 0.0247(7) -0.0080(6) -0.0022(5) -0.0088(6) O1 0.0306(6) 0.0293(6) 0.0275(6) -0.0037(5) -0.0055(5) -0.0013(5) O2 0.0365(7) 0.0226(5) 0.0237(6) -0.0059(4) -0.0038(5) -0.0028(5) O3 0.0391(7) 0.0232(6) 0.0243(6) -0.0062(5) -0.0051(5) -0.0064(5) O4 0.0284(6) 0.0340(6) 0.0267(6) -0.0076(5) -0.0052(5) -0.0058(5) C1 0.0582(14) 0.0346(11) 0.0464(12) -0.0073(9) -0.0197(11) 0.0077(10) C2 0.0348(9) 0.0266(8) 0.0348(9) -0.0030(7) -0.0078(7) -0.0025(7) C3 0.0529(12) 0.0278(9) 0.0376(10) -0.0105(8) -0.0117(9) 0.0061(9) C4 0.0352(9) 0.0227(7) 0.0273(8) -0.0059(6) -0.0023(7) -0.0060(7) C5 0.0406(10) 0.0216(8) 0.0281(8) -0.0083(6) -0.0021(7) -0.0043(7) C6 0.0330(9) 0.0210(7) 0.0253(8) -0.0076(6) 0.0010(6) -0.0056(6) C7 0.0384(9) 0.0232(8) 0.0241(8) -0.0083(6) 0.0008(7) -0.0068(7) C8 0.0757(16) 0.0294(9) 0.0320(10) -0.0154(8) -0.0079(10) -0.0027(10) C9 0.104(2) 0.0262(10) 0.0460(13) -0.0187(9) -0.0185(14) 0.0092(12) C10 0.0802(17) 0.0223(9) 0.0398(11) -0.0097(8) -0.0158(11) 0.0046(10) C11 0.0292(8) 0.0261(8) 0.0236(8) -0.0080(6) 0.0028(6) -0.0075(6) C12 0.0435(10) 0.0319(9) 0.0284(9) -0.0114(7) -0.0049(7) -0.0097(8) C13 0.0260(8) 0.0389(9) 0.0273(8) -0.0124(7) 0.0002(6) -0.0087(7) C14 0.0434(11) 0.0472(12) 0.0328(10) -0.0155(9) -0.0099(8) -0.0072(9) C15 0.0292(9) 0.0414(11) 0.0390(10) -0.0039(8) -0.0026(8) -0.0064(8) C16 0.0249(9) 0.0633(15) 0.0477(12) -0.0111(11) -0.0020(8) -0.0084(9) C17 0.0312(10) 0.0719(15) 0.0395(11) -0.0143(10) 0.0048(8) -0.0254(10) C18 0.0428(11) 0.0527(12) 0.0297(9) -0.0065(8) 0.0020(8) -0.0254(10) C19 0.0316(9) 0.0382(9) 0.0252(8) -0.0083(7) -0.0020(7) -0.0111(8) C20 0.0752(19) 0.0439(13) 0.0516(15) 0.0030(11) 0.0160(14) -0.0055(13) C21 0.0670(18) 0.0458(14) 0.084(2) 0.0047(14) -0.0325(16) -0.0149(13) N20 0.0498(14) 0.0436(13) 0.101(2) 0.0110(14) 0.0110(15) -0.0065(11) C22 0.0498(14) 0.0436(13) 0.101(2) 0.0110(14) 0.0110(15) -0.0065(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9282(12) . ? Cu1 O2 1.9304(12) . ? Cu1 O3 1.9326(12) 2_757 ? Cu1 O4 1.9496(13) 2_757 ? Cu1 N1 2.2546(15) . ? N1 C15 1.332(2) . ? N1 C19 1.331(2) . ? O1 C2 1.267(2) . ? O2 C4 1.264(2) . ? O3 C11 1.272(2) . ? O3 Cu1 1.9326(12) 2_757 ? O4 C13 1.266(2) . ? O4 Cu1 1.9496(12) 2_757 ? C1 C2 1.506(3) . ? C1 H1A 0.9600 . ? C1 H1C 0.9600 . ? C1 H1B 0.9600 . ? C2 C3 1.385(3) . ? C3 C4 1.398(3) . ? C3 H3 0.9300 . ? C4 C5 1.492(2) . ? C5 C6 1.387(2) . ? C5 C10 1.394(2) . ? C6 C7 1.389(2) . ? C6 H6 0.9300 . ? C7 C8 1.396(2) . ? C7 C11 1.491(2) . ? C8 C9 1.372(3) . ? C8 H8 0.9300 . ? C9 C10 1.370(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.398(2) . ? C12 C13 1.393(3) . ? C12 H12 0.9300 . ? C13 C14 1.513(3) . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C14 H14A 0.9600 . ? C15 C16 1.375(3) . ? C15 H15 0.9300 . ? C16 C17 1.373(3) . ? C16 H16 0.9300 . ? C17 C18 1.378(3) . ? C17 H17 0.9300 . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 N20 1.333(4) . ? C20 C21 1.333(5) 2_657 ? C20 H20 0.9300 . ? C21 C20 1.333(5) 2_657 ? C21 N20 1.372(4) . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O2 93.02(5) . . ? O1 Cu1 O3 169.16(6) . 2_757 ? O2 Cu1 O3 85.29(5) . 2_757 ? O1 Cu1 O4 87.12(5) . 2_757 ? O2 Cu1 O4 167.54(6) . 2_757 ? O3 Cu1 O4 92.24(5) 2_757 2_757 ? O1 Cu1 N1 96.21(6) . . ? O2 Cu1 N1 97.54(6) . . ? O3 Cu1 N1 94.63(6) 2_757 . ? O4 Cu1 N1 94.83(5) 2_757 . ? C15 N1 C19 117.43(17) . . ? C15 N1 Cu1 120.38(13) . . ? C19 N1 Cu1 122.18(12) . . ? C2 O1 Cu1 124.95(12) . . ? C4 O2 Cu1 126.55(12) . . ? C11 O3 Cu1 127.01(12) . 2_757 ? C13 O4 Cu1 125.58(12) . 2_757 ? C2 C1 H1A 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? O1 C2 C3 126.24(17) . . ? O1 C2 C1 115.15(17) . . ? C3 C2 C1 118.61(18) . . ? C2 C3 C4 124.65(18) . . ? C2 C3 H3 117.7 . . ? C4 C3 H3 117.7 . . ? O2 C4 C3 124.26(17) . . ? O2 C4 C5 115.66(15) . . ? C3 C4 C5 120.07(16) . . ? C6 C5 C10 118.36(17) . . ? C6 C5 C4 119.80(15) . . ? C10 C5 C4 121.83(17) . . ? C5 C6 C7 121.45(16) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C8 118.71(17) . . ? C6 C7 C11 119.64(15) . . ? C8 C7 C11 121.64(16) . . ? C9 C8 C7 120.01(19) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 120.88(19) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C5 120.58(19) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? O3 C11 C12 124.49(17) . . ? O3 C11 C7 114.96(15) . . ? C12 C11 C7 120.55(16) . . ? C13 C12 C11 124.42(17) . . ? C13 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? O4 C13 C12 125.94(16) . . ? O4 C13 C14 115.29(17) . . ? C12 C13 C14 118.76(17) . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? N1 C15 C16 123.2(2) . . ? N1 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C17 C16 C15 118.9(2) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 118.93(19) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C19 118.3(2) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? N1 C19 C18 123.26(19) . . ? N1 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? N20 C20 C21 119.3(3) . 2_657 ? N20 C20 H20 120.3 . . ? C21 C20 H20 120.3 2_657 . ? C20 C21 N20 120.2(3) 2_657 . ? C20 C21 H21 119.9 2_657 . ? N20 C21 H21 119.9 . . ? C20 N20 C21 120.4(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.534 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.069 # Attachment 'Fig_2_Cu_etpy.CIF' data_lj85sad _database_code_depnum_ccdc_archive 'CCDC 754706' #TrackingRef 'Fig_2_Cu_etpy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H66 Cu2 N2 O8, 2(C7 H9 N)' _chemical_formula_sum 'C68 H84 Cu2 N4 O8' _chemical_formula_weight 1212.47 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-p 1' #_symmetry_international_tables_no '2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.013(1) _cell_length_b 11.390(1) _cell_length_c 13.365(1) _cell_angle_alpha 81.312(2) _cell_angle_beta 78.572(2) _cell_angle_gamma 76.639(2) _cell_volume 1589.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7097 _cell_measurement_theta_min 2.377 _cell_measurement_theta_max 22.77 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.373 _exptl_crystal_size_mid 0.290 _exptl_crystal_size_min 0.110 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 642 _exptl_absorpt_coefficient_mu 0.726 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_t_min 0.572 _exptl_absorpt_correction_t_max 0.923 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 58035 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 30.55 _reflns_number_total 9598 _reflns_number_gt 6904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius,2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius,2003)' _computing_data_reduction 'SAINT and XPREP (Bruker-Nonius 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.1135P)^2^+2.4257P] 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 9598 _refine_ls_number_parameters 360 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2267 _refine_ls_wR_factor_gt 0.2078 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 C1A C 0.1779(9) 0.4219(7) 1.0436(7) 0.0450(11) Uani 0.65 1 d P A 1 H1A1 H 0.1467 0.3522 1.0316 0.067 Uiso 0.65 1 calc PR A 1 H1A2 H 0.1065 0.4906 1.0559 0.067 Uiso 0.65 1 calc PR A 1 H1A3 H 0.2204 0.4003 1.1037 0.067 Uiso 0.65 1 calc PR A 1 C3A C 0.3006(8) 0.5808(9) 0.9597(6) 0.0450(11) Uani 0.65 1 d P A 1 H3A1 H 0.2220 0.6426 0.9679 0.067 Uiso 0.65 1 calc PR A 1 H3A2 H 0.3570 0.6044 0.8971 0.067 Uiso 0.65 1 calc PR A 1 H3A3 H 0.3424 0.5738 1.0192 0.067 Uiso 0.65 1 calc PR A 1 C1B C 0.2601(16) 0.5764(19) 0.9884(11) 0.0450(11) Uani 0.35 1 d P A 2 H1B1 H 0.1712 0.6112 1.0138 0.067 Uiso 0.35 1 calc PR A 2 H1B2 H 0.2937 0.6315 0.9317 0.067 Uiso 0.35 1 calc PR A 2 H1B3 H 0.3092 0.5649 1.0441 0.067 Uiso 0.35 1 calc PR A 2 C3B C 0.1876(19) 0.3755(13) 1.0394(13) 0.0450(11) Uani 0.35 1 d P A 2 H3B1 H 0.2177 0.3684 1.1048 0.067 Uiso 0.35 1 calc PR A 2 H3B2 H 0.1985 0.2943 1.0185 0.067 Uiso 0.35 1 calc PR A 2 H3B3 H 0.0978 0.4152 1.0477 0.067 Uiso 0.35 1 calc PR A 2 C2 C 0.3976(4) 0.3660(5) 0.9433(4) 0.0529(12) Uani 1 1 d . A . H2A H 0.4363 0.3659 1.0034 0.079 Uiso 1 1 calc R . . H2B H 0.4538 0.3900 0.8808 0.079 Uiso 1 1 calc R . . H2C H 0.3845 0.2844 0.9406 0.079 Uiso 1 1 calc R . . C4 C 0.2695(3) 0.4564(3) 0.9515(3) 0.0276(7) Uani 1 1 d . . . C5 C 0.2125(3) 0.4587(3) 0.8546(2) 0.0222(6) Uani 1 1 d . A . C6 C 0.1462(3) 0.5674(3) 0.8091(3) 0.0253(6) Uani 1 1 d . . . H6 H 0.1439 0.6405 0.8363 0.030 Uiso 1 1 calc R A . C7 C 0.0833(3) 0.5754(3) 0.7265(2) 0.0196(5) Uani 1 1 d . A . C8 C 0.0111(3) 0.6959(3) 0.6855(2) 0.0194(5) Uani 1 1 d . . . C9 C -0.0439(3) 0.7015(3) 0.5987(2) 0.0205(6) Uani 1 1 d . A . H9 H -0.0373 0.6289 0.5693 0.025 Uiso 1 1 calc R . . C10 C -0.1078(3) 0.8103(3) 0.5545(2) 0.0213(6) Uani 1 1 d D . . C11 C -0.1195(4) 0.9169(3) 0.5988(3) 0.0318(7) Uani 1 1 d . A . H11 H -0.1648 0.9919 0.5704 0.038 Uiso 1 1 calc R . . C12 C -0.0647(5) 0.9124(3) 0.6843(3) 0.0479(12) Uani 1 1 d . . . H12 H -0.0713 0.9852 0.7134 0.057 Uiso 1 1 calc R A . C13 C -0.0006(4) 0.8038(3) 0.7280(3) 0.0365(9) Uani 1 1 d . A . H13 H 0.0356 0.8024 0.7872 0.044 Uiso 1 1 calc R . . C14 C -0.1619(3) 0.8113(2) 0.4582(2) 0.0242(6) Uani 1 1 d D A . C15A C -0.2231(6) 0.9192(5) 0.4100(5) 0.0487(6) Uani 0.75 1 d PD A 1 H15A H -0.2255 0.9927 0.4366 0.058 Uiso 0.75 1 calc PR A 1 C16A C -0.2812(7) 0.9262(8) 0.3249(5) 0.0487(6) Uani 0.75 1 d P A 1 C17A C -0.3376(7) 1.0546(5) 0.2703(5) 0.0487(6) Uani 0.75 1 d P A 1 C18A C -0.4690(7) 1.0364(5) 0.2532(6) 0.0487(6) Uani 0.75 1 d P A 1 H18A H -0.5254 1.0302 0.3195 0.073 Uiso 0.75 1 calc PR A 1 H18B H -0.4565 0.9619 0.2208 0.073 Uiso 0.75 1 calc PR A 1 H18C H -0.5069 1.1059 0.2085 0.073 Uiso 0.75 1 calc PR A 1 C19A C -0.3331(7) 1.1595(5) 0.3195(5) 0.0487(6) Uani 0.75 1 d P A 1 H19A H -0.3770 1.2338 0.2836 0.073 Uiso 0.75 1 calc PR A 1 H19B H -0.2447 1.1641 0.3165 0.073 Uiso 0.75 1 calc PR A 1 H19C H -0.3747 1.1509 0.3914 0.073 Uiso 0.75 1 calc PR A 1 C20A C -0.2623(6) 1.0732(5) 0.1598(5) 0.0487(6) Uani 0.75 1 d P A 1 H20A H -0.3061 1.1464 0.1225 0.073 Uiso 0.75 1 calc PR A 1 H20B H -0.2565 1.0026 0.1239 0.073 Uiso 0.75 1 calc PR A 1 H20C H -0.1770 1.0822 0.1634 0.073 Uiso 0.75 1 calc PR A 1 C15B C -0.2577(5) 0.9053(3) 0.4288(3) 0.0487(6) Uani 0.25 1 d PD A 2 H15B H -0.2905 0.9673 0.4731 0.058 Uiso 0.25 1 calc PR A 2 C16B C -0.310(2) 0.917(2) 0.3405(11) 0.0487(6) Uani 0.25 1 d PD A 2 C18B C -0.5051(19) 1.0622(15) 0.4106(15) 0.0487(6) Uani 0.25 1 d P A 2 H18D H -0.4643 1.0884 0.4597 0.073 Uiso 0.25 1 calc PR A 2 H18E H -0.5398 0.9908 0.4424 0.073 Uiso 0.25 1 calc PR A 2 H18F H -0.5738 1.1281 0.3910 0.073 Uiso 0.25 1 calc PR A 2 C17B C -0.411(2) 1.0308(15) 0.3185(16) 0.0487(6) Uani 0.25 1 d P A 2 C19B C -0.335(2) 1.1334(16) 0.2712(16) 0.0487(6) Uani 0.25 1 d P A 2 H19D H -0.3819 1.1912 0.2229 0.073 Uiso 0.25 1 calc PR A 2 H19E H -0.2518 1.0968 0.2348 0.073 Uiso 0.25 1 calc PR A 2 H19F H -0.3246 1.1760 0.3263 0.073 Uiso 0.25 1 calc PR A 2 C20B C -0.477(2) 1.0023(17) 0.2263(17) 0.0487(6) Uani 0.25 1 d P A 2 H20D H -0.5192 0.9340 0.2512 0.073 Uiso 0.25 1 calc PR A 2 H20E H -0.4113 0.9817 0.1668 0.073 Uiso 0.25 1 calc PR A 2 H20F H -0.5392 1.0743 0.2064 0.073 Uiso 0.25 1 calc PR A 2 C21A C -0.0072(8) 0.1612(7) 0.8717(9) 0.0506(12) Uani 0.65 1 d P B 1 H21A H 0.0667 0.1321 0.9021 0.061 Uiso 0.65 1 calc PR B 1 C22A C -0.1122(7) 0.1073(7) 0.9079(7) 0.0506(12) Uani 0.65 1 d P B 1 H22A H -0.1074 0.0400 0.9594 0.061 Uiso 0.65 1 calc PR B 1 C23A C -0.2225(9) 0.1522(12) 0.8685(8) 0.0506(12) Uani 0.65 1 d P B 1 C26A C -0.3386(6) 0.0976(7) 0.9053(7) 0.0506(12) Uani 0.65 1 d P B 1 H26A H -0.3826 0.1281 0.9713 0.061 Uiso 0.65 1 calc PR B 1 H26B H -0.3969 0.1266 0.8550 0.061 Uiso 0.65 1 calc PR B 1 C27A C -0.3127(7) -0.0394(7) 0.9203(7) 0.0506(12) Uani 0.65 1 d P B 1 H27A H -0.3926 -0.0666 0.9454 0.076 Uiso 0.65 1 calc PR B 1 H27B H -0.2557 -0.0695 0.9705 0.076 Uiso 0.65 1 calc PR B 1 H27C H -0.2731 -0.0710 0.8547 0.076 Uiso 0.65 1 calc PR B 1 C21B C -0.0107(16) 0.1951(13) 0.8870(17) 0.0506(12) Uani 0.35 1 d P B 2 H21B H 0.0608 0.1870 0.9192 0.061 Uiso 0.35 1 calc PR B 2 C22B C -0.1102(13) 0.1447(13) 0.9414(13) 0.0506(12) Uani 0.35 1 d P B 2 H22B H -0.1076 0.1063 1.0094 0.061 Uiso 0.35 1 calc PR B 2 C23B C -0.2173(18) 0.151(2) 0.8938(15) 0.0506(12) Uani 0.35 1 d P B 2 C26B C -0.3299(12) 0.0998(14) 0.9513(13) 0.0506(12) Uani 0.35 1 d P B 2 H26C H -0.4024 0.1304 0.9143 0.061 Uiso 0.35 1 calc PR B 2 H26D H -0.3547 0.1275 1.0206 0.061 Uiso 0.35 1 calc PR B 2 C27B C -0.2981(12) -0.0399(14) 0.9612(13) 0.0506(12) Uani 0.35 1 d P B 2 H27D H -0.3732 -0.0710 0.9961 0.076 Uiso 0.35 1 calc PR B 2 H27E H -0.2294 -0.0703 1.0011 0.076 Uiso 0.35 1 calc PR B 2 H27F H -0.2715 -0.0673 0.8926 0.076 Uiso 0.35 1 calc PR B 2 C24 C -0.2196(4) 0.2358(4) 0.7925(3) 0.0391(9) Uani 1 1 d . . . H24 H -0.2929 0.2657 0.7615 0.047 Uiso 1 1 calc R B 1 C25 C -0.1129(4) 0.2837(4) 0.7543(3) 0.0357(8) Uani 1 1 d . B . H25 H -0.1150 0.3420 0.6954 0.043 Uiso 1 1 calc R . . C28 C 0.7298(4) 0.2759(4) 0.5299(3) 0.0433(9) Uani 1 1 d . . . H28 H 0.8036 0.2319 0.4912 0.052 Uiso 1 1 calc R . . C29 C 0.7250(4) 0.3962(4) 0.5355(3) 0.0362(8) Uani 1 1 d . . . H29 H 0.7940 0.4326 0.5023 0.043 Uiso 1 1 calc R . . C30 C 0.6178(4) 0.4643(4) 0.5904(3) 0.0422(10) Uani 1 1 d . . . C31 C 0.5204(4) 0.4037(5) 0.6352(4) 0.0540(13) Uani 1 1 d . . . H31 H 0.4444 0.4458 0.6727 0.065 Uiso 1 1 calc R . . C32 C 0.5353(4) 0.2822(5) 0.6247(4) 0.0557(14) Uani 1 1 d . . . H32 H 0.4671 0.2435 0.6555 0.067 Uiso 1 1 calc R . . C33 C 0.6104(5) 0.5947(4) 0.6039(4) 0.0584(14) Uani 1 1 d . . . H33A H 0.5220 0.6403 0.6056 0.070 Uiso 1 1 calc R . . H33B H 0.6640 0.6315 0.5446 0.070 Uiso 1 1 calc R . . C34 C 0.6548(5) 0.6049(5) 0.7031(5) 0.0606(14) Uani 1 1 d . . . H34A H 0.6485 0.6906 0.7101 0.091 Uiso 1 1 calc R . . H34B H 0.7429 0.5614 0.7009 0.091 Uiso 1 1 calc R . . H34C H 0.6013 0.5692 0.7619 0.091 Uiso 1 1 calc R . . N1 N -0.0077(3) 0.2530(3) 0.7950(2) 0.0303(6) Uani 1 1 d . . . N2 N 0.6387(4) 0.2155(4) 0.5745(3) 0.0517(10) Uani 1 1 d . . . O1 O 0.2280(2) 0.3556(2) 0.82402(19) 0.0287(5) Uani 1 1 d . . . O2 O 0.0828(2) 0.4869(2) 0.67914(18) 0.0280(5) Uani 1 1 d . . . O3 O -0.1354(2) 0.70677(18) 0.42344(18) 0.0257(5) Uani 1 1 d D . . O4 O -0.2766(2) 0.8388(2) 0.27524(17) 0.0272(5) Uani 1 1 d D . . Cu1 Cu 0.16732(4) 0.31974(3) 0.70789(3) 0.02175(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.065(3) 0.048(3) 0.032(2) -0.002(3) -0.022(2) -0.022(3) C3A 0.065(3) 0.048(3) 0.032(2) -0.002(3) -0.022(2) -0.022(3) C1B 0.065(3) 0.048(3) 0.032(2) -0.002(3) -0.022(2) -0.022(3) C3B 0.065(3) 0.048(3) 0.032(2) -0.002(3) -0.022(2) -0.022(3) C2 0.044(2) 0.062(3) 0.056(3) -0.021(2) -0.032(2) 0.011(2) C4 0.0323(16) 0.0297(16) 0.0239(15) -0.0057(12) -0.0140(13) -0.0029(13) C5 0.0225(14) 0.0248(14) 0.0205(14) -0.0024(11) -0.0069(11) -0.0045(11) C6 0.0325(16) 0.0199(14) 0.0258(15) -0.0056(12) -0.0104(13) -0.0032(12) C7 0.0220(13) 0.0192(13) 0.0183(13) -0.0017(10) -0.0029(11) -0.0062(10) C8 0.0238(14) 0.0167(13) 0.0192(13) -0.0031(10) -0.0051(11) -0.0048(10) C9 0.0224(13) 0.0191(13) 0.0211(13) -0.0051(11) -0.0048(11) -0.0036(11) C10 0.0230(14) 0.0181(13) 0.0227(14) -0.0040(11) -0.0057(11) -0.0016(11) C11 0.048(2) 0.0165(14) 0.0329(18) -0.0046(12) -0.0189(16) 0.0018(13) C12 0.088(3) 0.0178(16) 0.045(2) -0.0099(15) -0.041(2) 0.0032(18) C13 0.062(2) 0.0209(15) 0.0320(18) -0.0077(13) -0.0270(17) -0.0002(15) C14 0.0273(15) 0.0196(14) 0.0268(15) -0.0057(11) -0.0085(12) -0.0014(11) C15A 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C16A 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C17A 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C18A 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C19A 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C20A 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C15B 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C16B 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C18B 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C17B 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C19B 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C20B 0.0632(15) 0.0280(10) 0.0546(15) -0.0051(10) -0.0278(12) 0.0066(10) C21A 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C22A 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C23A 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C26A 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C27A 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C21B 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C22B 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C23B 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C26B 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C27B 0.0272(10) 0.0481(15) 0.065(3) 0.029(2) -0.0111(14) -0.0035(11) C24 0.0256(17) 0.041(2) 0.051(2) -0.0050(18) -0.0132(16) -0.0021(15) C25 0.0310(17) 0.0365(19) 0.039(2) 0.0059(16) -0.0134(15) -0.0064(15) C28 0.039(2) 0.050(2) 0.042(2) -0.0001(19) -0.0070(18) -0.0152(18) C29 0.0313(18) 0.043(2) 0.0307(18) 0.0055(16) -0.0032(15) -0.0090(15) C30 0.0325(19) 0.049(2) 0.036(2) 0.0158(18) -0.0092(16) -0.0001(17) C31 0.0232(18) 0.077(3) 0.047(2) 0.022(2) -0.0046(17) 0.0007(19) C32 0.033(2) 0.071(3) 0.061(3) 0.026(3) -0.017(2) -0.022(2) C33 0.053(3) 0.042(2) 0.059(3) 0.012(2) 0.000(2) 0.012(2) C34 0.059(3) 0.039(2) 0.075(4) -0.007(2) -0.003(3) 0.000(2) N1 0.0269(14) 0.0298(14) 0.0332(15) 0.0042(12) -0.0116(12) -0.0034(11) N2 0.046(2) 0.058(2) 0.058(2) 0.0103(19) -0.0193(19) -0.0242(18) O1 0.0398(13) 0.0207(11) 0.0293(12) -0.0050(9) -0.0178(10) -0.0023(9) O2 0.0428(14) 0.0170(10) 0.0283(12) -0.0038(9) -0.0185(10) -0.0027(9) O3 0.0356(12) 0.0188(10) 0.0248(11) -0.0044(8) -0.0126(9) -0.0019(9) O4 0.0329(12) 0.0201(10) 0.0309(12) -0.0061(9) -0.0149(10) -0.0001(9) Cu1 0.0281(2) 0.01659(19) 0.0226(2) -0.00328(13) -0.01094(15) -0.00231(14) _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 C1A C4 1.494(10) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C3A C4 1.556(10) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? C1B C4 1.50(2) . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C3B C4 1.638(19) . ? C3B H3B1 0.9800 . ? C3B H3B2 0.9800 . ? C3B H3B3 0.9800 . ? C2 C4 1.538(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C4 C5 1.540(4) . ? C5 O1 1.266(4) . ? C5 C6 1.403(4) . ? C6 C7 1.397(4) . ? C6 H6 0.9500 . ? C7 O2 1.270(4) . ? C7 C8 1.502(4) . ? C8 C9 1.397(4) . ? C8 C13 1.400(4) . ? C9 C10 1.386(4) . ? C9 H9 0.9500 . ? C10 C11 1.398(4) . ? C10 C14 1.520(3) . ? C11 C12 1.383(5) . ? C11 H11 0.9500 . ? C12 C13 1.383(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.293(3) . ? C14 C15A 1.389(6) . ? C14 C15B 1.3889(10) . ? C15A C16A 1.395(8) . ? C15A H15A 0.9500 . ? C16A O4 1.264(8) . ? C16A C17A 1.579(9) . ? C17A C19A 1.463(8) . ? C17A C20A 1.554(10) . ? C17A C18A 1.572(10) . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C15B C16B 1.3869(10) . ? C15B H15B 0.9500 . ? C16B O4 1.28(2) . ? C16B C17B 1.54(3) . ? C18B C17B 1.47(3) . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C17B C19B 1.58(3) . ? C17B C20B 1.65(3) . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? C21A N1 1.349(9) . ? C21A C22A 1.402(11) . ? C21A H21A 0.9500 . ? C22A C23A 1.378(10) . ? C22A H22A 0.9500 . ? C23A C24 1.284(9) . ? C23A C26A 1.514(12) . ? C26A C27A 1.509(10) . ? C26A H26A 0.9900 . ? C26A H26B 0.9900 . ? C27A H27A 0.9800 . ? C27A H27B 0.9800 . ? C27A H27C 0.9800 . ? C21B N1 1.30(2) . ? C21B C22B 1.38(2) . ? C21B H21B 0.9500 . ? C22B C23B 1.43(2) . ? C22B H22B 0.9500 . ? C23B C26B 1.51(2) . ? C23B C24 1.540(15) . ? C26B C27B 1.54(2) . ? C26B H26C 0.9900 . ? C26B H26D 0.9900 . ? C27B H27D 0.9800 . ? C27B H27E 0.9800 . ? C27B H27F 0.9800 . ? C24 C25 1.383(6) . ? C24 H24 0.9500 . ? C25 N1 1.329(4) . ? C25 H25 0.9500 . ? C28 N2 1.338(6) . ? C28 C29 1.372(6) . ? C28 H28 0.9500 . ? C29 C30 1.392(6) . ? C29 H29 0.9500 . ? C30 C31 1.395(6) . ? C30 C33 1.505(7) . ? C31 C32 1.380(8) . ? C31 H31 0.9500 . ? C32 N2 1.334(7) . ? C32 H32 0.9500 . ? C33 C34 1.529(8) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? N1 Cu1 2.273(3) . ? O1 Cu1 1.937(2) . ? O2 Cu1 1.934(2) . ? O3 Cu1 1.936(2) 2_566 ? O4 Cu1 1.933(2) 2_566 ? Cu1 O4 1.933(2) 2_566 ? Cu1 O3 1.936(2) 2_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C1A H1A1 109.5 . . ? C4 C1A H1A2 109.5 . . ? C4 C1A H1A3 109.5 . . ? C4 C3A H3A1 109.5 . . ? C4 C3A H3A2 109.5 . . ? C4 C3A H3A3 109.5 . . ? C4 C1B H1B1 109.5 . . ? C4 C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C4 C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? C4 C3B H3B1 109.5 . . ? C4 C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C4 C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1A C4 C1B 90.8(7) . . ? C1A C4 C2 112.0(5) . . ? C1B C4 C2 118.5(7) . . ? C1A C4 C5 108.6(4) . . ? C1B C4 C5 116.8(6) . . ? C2 C4 C5 108.7(3) . . ? C1A C4 C3A 110.4(5) . . ? C2 C4 C3A 105.1(5) . . ? C5 C4 C3A 112.1(4) . . ? C1B C4 C3B 108.7(8) . . ? C2 C4 C3B 98.1(7) . . ? C5 C4 C3B 103.3(5) . . ? C3A C4 C3B 127.7(7) . . ? O1 C5 C6 124.8(3) . . ? O1 C5 C4 114.2(3) . . ? C6 C5 C4 121.0(3) . . ? C7 C6 C5 124.3(3) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? O2 C7 C6 125.1(3) . . ? O2 C7 C8 114.7(3) . . ? C6 C7 C8 120.2(3) . . ? C9 C8 C13 118.2(3) . . ? C9 C8 C7 118.6(3) . . ? C13 C8 C7 123.2(3) . . ? C10 C9 C8 121.7(3) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 119.2(2) . . ? C9 C10 C14 119.2(3) . . ? C11 C10 C14 121.5(2) . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 121.1(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C8 120.2(3) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O3 C14 C15A 125.3(4) . . ? O3 C14 C15B 122.6(2) . . ? O3 C14 C10 113.58(17) . . ? C15A C14 C10 120.8(3) . . ? C15B C14 C10 121.5(2) . . ? C14 C15A C16A 123.9(6) . . ? C14 C15A H15A 118.0 . . ? C16A C15A H15A 118.0 . . ? O4 C16A C15A 125.6(6) . . ? O4 C16A C17A 113.8(5) . . ? C15A C16A C17A 119.6(6) . . ? C19A C17A C20A 105.2(6) . . ? C19A C17A C18A 119.2(6) . . ? C20A C17A C18A 104.0(5) . . ? C19A C17A C16A 115.8(5) . . ? C20A C17A C16A 109.9(5) . . ? C18A C17A C16A 102.0(5) . . ? C16B C15B C14 125.8(11) . . ? C16B C15B H15B 117.1 . . ? C14 C15B H15B 117.1 . . ? O4 C16B C15B 123.8(18) . . ? O4 C16B C17B 118.0(8) . . ? C15B C16B C17B 118.2(17) . . ? C17B C18B H18D 109.5 . . ? C17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C18B C17B C16B 112.5(16) . . ? C18B C17B C19B 113.3(16) . . ? C16B C17B C19B 105.1(17) . . ? C18B C17B C20B 112.1(18) . . ? C16B C17B C20B 106.1(13) . . ? C19B C17B C20B 107.1(16) . . ? C17B C19B H19D 109.5 . . ? C17B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C17B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C17B C20B H20D 109.5 . . ? C17B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C17B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? N1 C21A C22A 122.1(7) . . ? N1 C21A H21A 119.0 . . ? C22A C21A H21A 119.0 . . ? C23A C22A C21A 119.9(7) . . ? C23A C22A H22A 120.1 . . ? C21A C22A H22A 120.1 . . ? C24 C23A C22A 117.1(9) . . ? C24 C23A C26A 120.7(7) . . ? C22A C23A C26A 121.9(7) . . ? C27A C26A C23A 115.1(7) . . ? C27A C26A H26A 108.5 . . ? C23A C26A H26A 108.5 . . ? C27A C26A H26B 108.5 . . ? C23A C26A H26B 108.5 . . ? H26A C26A H26B 107.5 . . ? C26A C27A H27A 109.5 . . ? C26A C27A H27B 109.5 . . ? H27A C27A H27B 109.5 . . ? C26A C27A H27C 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? N1 C21B C22B 124.9(15) . . ? N1 C21B H21B 117.6 . . ? C22B C21B H21B 117.6 . . ? C21B C22B C23B 119.0(14) . . ? C21B C22B H22B 120.5 . . ? C23B C22B H22B 120.5 . . ? C22B C23B C26B 120.9(13) . . ? C22B C23B C24 114.4(15) . . ? C26B C23B C24 123.5(12) . . ? C23B C26B C27B 110.9(13) . . ? C23B C26B H26C 109.5 . . ? C27B C26B H26C 109.5 . . ? C23B C26B H26D 109.5 . . ? C27B C26B H26D 109.5 . . ? H26C C26B H26D 108.0 . . ? C26B C27B H27D 109.5 . . ? C26B C27B H27E 109.5 . . ? H27D C27B H27E 109.5 . . ? C26B C27B H27F 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? C23A C24 C25 122.0(6) . . ? C25 C24 C23B 116.4(8) . . ? C23A C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C23B C24 H24 123.9 . . ? N1 C25 C24 123.9(4) . . ? N1 C25 H25 118.1 . . ? C24 C25 H25 118.1 . . ? N2 C28 C29 125.2(4) . . ? N2 C28 H28 117.4 . . ? C29 C28 H28 117.4 . . ? C28 C29 C30 119.2(4) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C29 C30 C31 116.4(4) . . ? C29 C30 C33 121.4(4) . . ? C31 C30 C33 122.1(4) . . ? C32 C31 C30 119.6(4) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? N2 C32 C31 124.4(4) . . ? N2 C32 H32 117.8 . . ? C31 C32 H32 117.8 . . ? C30 C33 C34 111.3(4) . . ? C30 C33 H33A 109.4 . . ? C34 C33 H33A 109.4 . . ? C30 C33 H33B 109.4 . . ? C34 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C21B N1 C25 119.3(8) . . ? C25 N1 C21A 114.5(5) . . ? C21B N1 Cu1 121.9(8) . . ? C25 N1 Cu1 118.6(2) . . ? C21A N1 Cu1 124.8(4) . . ? C32 N2 C28 115.1(4) . . ? C5 O1 Cu1 126.8(2) . . ? C7 O2 Cu1 126.6(2) . . ? C14 O3 Cu1 124.43(16) . 2_566 ? C16A O4 Cu1 125.0(3) . 2_566 ? C16B O4 Cu1 126.2(7) . 2_566 ? O4 Cu1 O2 170.64(11) 2_566 . ? O4 Cu1 O3 92.70(9) 2_566 2_566 ? O2 Cu1 O3 86.94(9) . 2_566 ? O4 Cu1 O1 86.30(9) 2_566 . ? O2 Cu1 O1 92.28(10) . . ? O3 Cu1 O1 169.06(11) 2_566 . ? O4 Cu1 N1 93.17(11) 2_566 . ? O2 Cu1 N1 96.19(11) . . ? O3 Cu1 N1 92.65(11) 2_566 . ? O1 Cu1 N1 98.28(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A C4 C5 O1 -82.2(5) . . . . ? C1B C4 C5 O1 177.0(7) . . . . ? C2 C4 C5 O1 39.8(4) . . . . ? C3A C4 C5 O1 155.6(5) . . . . ? C3B C4 C5 O1 -63.7(7) . . . . ? C1A C4 C5 C6 95.7(5) . . . . ? C1B C4 C5 C6 -5.1(8) . . . . ? C2 C4 C5 C6 -142.3(4) . . . . ? C3A C4 C5 C6 -26.5(5) . . . . ? C3B C4 C5 C6 114.2(7) . . . . ? O1 C5 C6 C7 3.0(5) . . . . ? C4 C5 C6 C7 -174.6(3) . . . . ? C5 C6 C7 O2 -3.4(5) . . . . ? C5 C6 C7 C8 177.9(3) . . . . ? O2 C7 C8 C9 -2.8(4) . . . . ? C6 C7 C8 C9 176.0(3) . . . . ? O2 C7 C8 C13 179.3(3) . . . . ? C6 C7 C8 C13 -1.9(5) . . . . ? C13 C8 C9 C10 0.5(5) . . . . ? C7 C8 C9 C10 -177.6(3) . . . . ? C8 C9 C10 C11 -1.2(5) . . . . ? C8 C9 C10 C14 178.0(3) . . . . ? C9 C10 C11 C12 1.6(6) . . . . ? C14 C10 C11 C12 -177.6(4) . . . . ? C10 C11 C12 C13 -1.3(7) . . . . ? C11 C12 C13 C8 0.7(7) . . . . ? C9 C8 C13 C12 -0.2(6) . . . . ? C7 C8 C13 C12 177.7(4) . . . . ? C9 C10 C14 O3 -3.6(4) . . . . ? C11 C10 C14 O3 175.6(3) . . . . ? C9 C10 C14 C15A -178.0(4) . . . . ? C11 C10 C14 C15A 1.1(6) . . . . ? C9 C10 C14 C15B 159.7(4) . . . . ? C11 C10 C14 C15B -21.2(6) . . . . ? O3 C14 C15A C16A 10.0(9) . . . . ? C15B C14 C15A C16A -78.4(9) . . . . ? C10 C14 C15A C16A -176.3(6) . . . . ? C14 C15A C16A O4 -6.6(12) . . . . ? C14 C15A C16A C17A -174.7(6) . . . . ? O4 C16A C17A C19A -174.1(6) . . . . ? C15A C16A C17A C19A -4.7(10) . . . . ? O4 C16A C17A C20A -55.0(8) . . . . ? C15A C16A C17A C20A 114.4(7) . . . . ? O4 C16A C17A C18A 54.8(8) . . . . ? C15A C16A C17A C18A -135.8(7) . . . . ? O3 C14 C15B C16B -20.9(15) . . . . ? C15A C14 C15B C16B 83.6(16) . . . . ? C10 C14 C15B C16B 177.4(13) . . . . ? C14 C15B C16B O4 2(3) . . . . ? C14 C15B C16B C17B -177.2(14) . . . . ? O4 C16B C17B C18B 137.3(19) . . . . ? C15B C16B C17B C18B -44(3) . . . . ? O4 C16B C17B C19B -99(2) . . . . ? C15B C16B C17B C19B 80(2) . . . . ? O4 C16B C17B C20B 14(3) . . . . ? C15B C16B C17B C20B -166.8(18) . . . . ? N1 C21A C22A C23A -3.4(16) . . . . ? C21A C22A C23A C24 6.3(18) . . . . ? C21A C22A C23A C26A -179.8(10) . . . . ? C24 C23A C26A C27A 131.3(11) . . . . ? C22A C23A C26A C27A -42.4(15) . . . . ? N1 C21B C22B C23B 2(3) . . . . ? C21B C22B C23B C26B -178.5(17) . . . . ? C21B C22B C23B C24 -11(3) . . . . ? C22B C23B C26B C27B -74(3) . . . . ? C24 C23B C26B C27B 119.8(19) . . . . ? C22A C23A C24 C25 -3.1(16) . . . . ? C26A C23A C24 C25 -177.1(8) . . . . ? C22A C23A C24 C23B -61(6) . . . . ? C26A C23A C24 C23B 125(7) . . . . ? C22B C23B C24 C23A 134(8) . . . . ? C26B C23B C24 C23A -59(6) . . . . ? C22B C23B C24 C25 7(2) . . . . ? C26B C23B C24 C25 174.4(16) . . . . ? C23A C24 C25 N1 -3.6(10) . . . . ? C23B C24 C25 N1 5.7(13) . . . . ? N2 C28 C29 C30 -0.7(7) . . . . ? C28 C29 C30 C31 -0.9(6) . . . . ? C28 C29 C30 C33 176.6(4) . . . . ? C29 C30 C31 C32 1.0(6) . . . . ? C33 C30 C31 C32 -176.5(4) . . . . ? C30 C31 C32 N2 0.6(7) . . . . ? C29 C30 C33 C34 -92.3(5) . . . . ? C31 C30 C33 C34 85.1(5) . . . . ? C22B C21B N1 C25 11(2) . . . . ? C22B C21B N1 C21A -70(3) . . . . ? C22B C21B N1 Cu1 -175.2(12) . . . . ? C24 C25 N1 C21B -15.0(11) . . . . ? C24 C25 N1 C21A 6.4(8) . . . . ? C24 C25 N1 Cu1 170.9(3) . . . . ? C22A C21A N1 C21B 106(3) . . . . ? C22A C21A N1 C25 -2.9(11) . . . . ? C22A C21A N1 Cu1 -166.3(7) . . . . ? C31 C32 N2 C28 -2.2(7) . . . . ? C29 C28 N2 C32 2.2(7) . . . . ? C6 C5 O1 Cu1 0.6(5) . . . . ? C4 C5 O1 Cu1 178.4(2) . . . . ? C6 C7 O2 Cu1 0.1(5) . . . . ? C8 C7 O2 Cu1 178.8(2) . . . . ? C15A C14 O3 Cu1 3.7(5) . . . 2_566 ? C15B C14 O3 Cu1 26.5(5) . . . 2_566 ? C10 C14 O3 Cu1 -170.5(2) . . . 2_566 ? C15A C16A O4 C16B 90(3) . . . . ? C17A C16A O4 C16B -101(3) . . . . ? C15A C16A O4 Cu1 -9.9(10) . . . 2_566 ? C17A C16A O4 Cu1 158.7(4) . . . 2_566 ? C15B C16B O4 C16A -83(3) . . . . ? C17B C16B O4 C16A 96(4) . . . . ? C15B C16B O4 Cu1 9(3) . . . 2_566 ? C17B C16B O4 Cu1 -172.1(13) . . . 2_566 ? C7 O2 Cu1 O3 -166.7(3) . . . 2_566 ? C7 O2 Cu1 O1 2.4(3) . . . . ? C7 O2 Cu1 N1 101.0(3) . . . . ? C5 O1 Cu1 O4 168.0(3) . . . 2_566 ? C5 O1 Cu1 O2 -2.7(3) . . . . ? C5 O1 Cu1 O3 82.9(6) . . . 2_566 ? C5 O1 Cu1 N1 -99.3(3) . . . . ? C21B N1 Cu1 O4 53.7(9) . . . 2_566 ? C25 N1 Cu1 O4 -132.4(3) . . . 2_566 ? C21A N1 Cu1 O4 30.4(6) . . . 2_566 ? C21B N1 Cu1 O2 -126.3(9) . . . . ? C25 N1 Cu1 O2 47.6(3) . . . . ? C21A N1 Cu1 O2 -149.6(6) . . . . ? C21B N1 Cu1 O3 146.5(9) . . . 2_566 ? C25 N1 Cu1 O3 -39.6(3) . . . 2_566 ? C21A N1 Cu1 O3 123.2(6) . . . 2_566 ? C21B N1 Cu1 O1 -33.0(10) . . . . ? C25 N1 Cu1 O1 140.8(3) . . . . ? C21A N1 Cu1 O1 -56.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 3.034 _refine_diff_density_min -1.958 _refine_diff_density_rms 0.116 # Attachment 'Fig_4.CIF' data_lj249sad _database_code_depnum_ccdc_archive 'CCDC 754707' #TrackingRef 'Fig_4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C60 H92 N4 Ni2 O8, C5 H11 N' _chemical_formula_sum 'C65 H103 N5 Ni2 O8' _chemical_formula_weight 1199.94 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' 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 P21/n _symmetry_space_group_name_Hall '-P 2yn' #_symmetry_international_tables_no '14' 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 22.411(3) _cell_length_b 10.9718(15) _cell_length_c 27.490(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.990(2) _cell_angle_gamma 90.00 _cell_volume 6612.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6552 _cell_measurement_theta_min 2.267 _cell_measurement_theta_max 24.90 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.624 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 53078 _diffrn_reflns_av_R_equivalents 0.0853 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.32 _reflns_number_total 12025 _reflns_number_gt 7701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0484P)^2^+0.8661P] 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 12025 _refine_ls_number_parameters 770 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.038 _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 0.1640(2) -0.2790(3) 0.43072(14) 0.0613(13) Uani 1 1 d . . . H1A H 0.1991 -0.2767 0.4146 0.092 Uiso 1 1 calc R . . H1B H 0.1460 -0.1974 0.4300 0.092 Uiso 1 1 calc R . . H1C H 0.1335 -0.3363 0.4130 0.092 Uiso 1 1 calc R . . C2 C 0.21492(16) -0.4451(3) 0.48617(14) 0.0398(9) Uani 1 1 d . . . H2A H 0.2502 -0.4405 0.4703 0.060 Uiso 1 1 calc R . . H2B H 0.1856 -0.5043 0.4684 0.060 Uiso 1 1 calc R . . H2C H 0.2284 -0.4707 0.5209 0.060 Uiso 1 1 calc R . . C3 C 0.12889(16) -0.3303(3) 0.50830(17) 0.0567(12) Uani 1 1 d . . . H3A H 0.1003 -0.3900 0.4899 0.085 Uiso 1 1 calc R . . H3B H 0.1088 -0.2507 0.5073 0.085 Uiso 1 1 calc R . . H3C H 0.1419 -0.3568 0.5429 0.085 Uiso 1 1 calc R . . C4 C 0.18475(15) -0.3201(3) 0.48442(13) 0.0328(8) Uani 1 1 d . . . C5 C 0.22547(14) -0.2183(3) 0.51217(11) 0.0257(7) Uani 1 1 d . . . C6 C 0.28486(14) -0.2439(3) 0.53865(12) 0.0263(7) Uani 1 1 d . . . H6 H 0.2976 -0.3267 0.5403 0.032 Uiso 1 1 calc R . . C7 C 0.32667(14) -0.1577(3) 0.56273(11) 0.0225(7) Uani 1 1 d . . . C8 C 0.38823(13) -0.1995(3) 0.59132(11) 0.0215(7) Uani 1 1 d . . . C9 C 0.42752(14) -0.1132(3) 0.61806(11) 0.0238(7) Uani 1 1 d . . . H9 H 0.4149 -0.0304 0.6172 0.029 Uiso 1 1 calc R . . C10 C 0.48478(14) -0.1448(3) 0.64601(11) 0.0233(7) Uani 1 1 d . . . C11 C 0.50195(15) -0.2670(3) 0.64680(12) 0.0313(8) Uani 1 1 d . . . H11 H 0.5408 -0.2913 0.6653 0.038 Uiso 1 1 calc R . . C12 C 0.46310(15) -0.3528(3) 0.62096(13) 0.0320(8) Uani 1 1 d . . . H12 H 0.4752 -0.4359 0.6222 0.038 Uiso 1 1 calc R . . C13 C 0.40682(15) -0.3198(3) 0.59329(12) 0.0290(8) Uani 1 1 d . . . H13 H 0.3807 -0.3802 0.5755 0.035 Uiso 1 1 calc R . . C14 C 0.52376(14) -0.0457(3) 0.67444(11) 0.0247(7) Uani 1 1 d . . . C15 C 0.57910(14) -0.0753(3) 0.70669(12) 0.0286(8) Uani 1 1 d . . . H15 H 0.5912 -0.1584 0.7084 0.034 Uiso 1 1 calc R . . C16 C 0.61810(14) 0.0083(3) 0.73665(11) 0.0251(7) Uani 1 1 d . A . C17 C 0.67861(14) -0.0343(3) 0.76947(12) 0.0289(8) Uani 1 1 d . . . C18 C 0.7291(5) 0.0541(13) 0.7611(5) 0.0390(16) Uani 0.50 1 d P A 1 H18A H 0.7161 0.1382 0.7650 0.058 Uiso 0.50 1 calc PR A 1 H18B H 0.7364 0.0428 0.7275 0.058 Uiso 0.50 1 calc PR A 1 H18C H 0.7667 0.0374 0.7855 0.058 Uiso 0.50 1 calc PR A 1 C19 C 0.6679(4) -0.0250(12) 0.8234(4) 0.0390(16) Uani 0.50 1 d P A 1 H19A H 0.7053 -0.0485 0.8470 0.058 Uiso 0.50 1 calc PR A 1 H19B H 0.6346 -0.0796 0.8272 0.058 Uiso 0.50 1 calc PR A 1 H19C H 0.6572 0.0591 0.8301 0.058 Uiso 0.50 1 calc PR A 1 C20 C 0.6974(5) -0.1613(10) 0.7596(4) 0.0390(16) Uani 0.50 1 d P A 1 H20A H 0.7009 -0.1683 0.7247 0.058 Uiso 0.50 1 calc PR A 1 H20B H 0.6667 -0.2191 0.7662 0.058 Uiso 0.50 1 calc PR A 1 H20C H 0.7369 -0.1797 0.7813 0.058 Uiso 0.50 1 calc PR A 1 C18A C 0.7247(10) 0.0634(19) 0.7761(6) 0.031(5) Uiso 0.25 1 d P A 2 H18D H 0.7628 0.0337 0.7970 0.046 Uiso 0.25 1 calc PR A 2 H18E H 0.7098 0.1336 0.7922 0.046 Uiso 0.25 1 calc PR A 2 H18F H 0.7321 0.0878 0.7436 0.046 Uiso 0.25 1 calc PR A 2 C19A C 0.7081(9) -0.1459(19) 0.7478(8) 0.040(6) Uiso 0.25 1 d P A 2 H19D H 0.7143 -0.1260 0.7145 0.061 Uiso 0.25 1 calc PR A 2 H19E H 0.6811 -0.2167 0.7460 0.061 Uiso 0.25 1 calc PR A 2 H19F H 0.7476 -0.1648 0.7695 0.061 Uiso 0.25 1 calc PR A 2 C20A C 0.6636(12) -0.073(2) 0.8199(10) 0.071(9) Uiso 0.25 1 d P A 2 H20D H 0.7016 -0.0840 0.8446 0.106 Uiso 0.25 1 calc PR A 2 H20E H 0.6408 -0.1499 0.8156 0.106 Uiso 0.25 1 calc PR A 2 H20F H 0.6389 -0.0098 0.8313 0.106 Uiso 0.25 1 calc PR A 2 C18B C 0.6839(8) 0.0223(15) 0.8224(6) 0.035(5) Uiso 0.25 1 d P A 3 H18G H 0.7233 0.0003 0.8433 0.053 Uiso 0.25 1 calc PR A 3 H18H H 0.6509 -0.0090 0.8373 0.053 Uiso 0.25 1 calc PR A 3 H18I H 0.6807 0.1113 0.8196 0.053 Uiso 0.25 1 calc PR A 3 C19B C 0.6855(7) -0.1707(14) 0.7752(5) 0.024(4) Uiso 0.25 1 d P A 3 H19G H 0.6810 -0.2083 0.7423 0.036 Uiso 0.25 1 calc PR A 3 H19H H 0.6540 -0.2025 0.7917 0.036 Uiso 0.25 1 calc PR A 3 H19I H 0.7259 -0.1899 0.7952 0.036 Uiso 0.25 1 calc PR A 3 C20B C 0.7289(10) 0.0206(19) 0.7461(7) 0.048(6) Uiso 0.25 1 d P A 3 H20G H 0.7175 0.1037 0.7347 0.072 Uiso 0.25 1 calc PR A 3 H20H H 0.7342 -0.0294 0.7177 0.072 Uiso 0.25 1 calc PR A 3 H20I H 0.7673 0.0227 0.7709 0.072 Uiso 0.25 1 calc PR A 3 C21 C 0.0526(2) 0.3703(4) 0.5169(2) 0.0512(14) Uani 0.80 1 d P B 1 H21A H 0.0756 0.3972 0.4922 0.077 Uiso 0.80 1 calc PR B 1 H21B H 0.0654 0.4179 0.5475 0.077 Uiso 0.80 1 calc PR B 1 H21C H 0.0089 0.3824 0.5039 0.077 Uiso 0.80 1 calc PR B 1 C22 C 0.0377(2) 0.1641(5) 0.4813(2) 0.0684(18) Uani 0.80 1 d P B 1 H22A H -0.0065 0.1767 0.4727 0.103 Uiso 0.80 1 calc PR B 1 H22B H 0.0464 0.0773 0.4875 0.103 Uiso 0.80 1 calc PR B 1 H22C H 0.0559 0.1913 0.4537 0.103 Uiso 0.80 1 calc PR B 1 C23 C 0.0354(2) 0.1967(6) 0.5697(2) 0.0601(16) Uani 0.80 1 d P B 1 H23A H -0.0085 0.2138 0.5609 0.090 Uiso 0.80 1 calc PR B 1 H23B H 0.0535 0.2409 0.6002 0.090 Uiso 0.80 1 calc PR B 1 H23C H 0.0418 0.1090 0.5751 0.090 Uiso 0.80 1 calc PR B 1 C21A C 0.0548(8) 0.2804(17) 0.4749(7) 0.041(5) Uiso 0.20 1 d P B 2 H21D H 0.0122 0.2668 0.4585 0.061 Uiso 0.20 1 calc PR B 2 H21E H 0.0815 0.2347 0.4573 0.061 Uiso 0.20 1 calc PR B 2 H21F H 0.0643 0.3675 0.4742 0.061 Uiso 0.20 1 calc PR B 2 C22A C 0.0327(10) 0.1216(19) 0.5366(9) 0.054(6) Uiso 0.20 1 d P B 2 H22D H -0.0114 0.1325 0.5254 0.081 Uiso 0.20 1 calc PR B 2 H22E H 0.0420 0.1018 0.5721 0.081 Uiso 0.20 1 calc PR B 2 H22F H 0.0465 0.0551 0.5179 0.081 Uiso 0.20 1 calc PR B 2 C23A C 0.0422(9) 0.3416(17) 0.5602(7) 0.042(5) Uiso 0.20 1 d P B 2 H23D H 0.0633 0.4180 0.5561 0.064 Uiso 0.20 1 calc PR B 2 H23E H 0.0512 0.3181 0.5953 0.064 Uiso 0.20 1 calc PR B 2 H23F H -0.0019 0.3529 0.5489 0.064 Uiso 0.20 1 calc PR B 2 C24 C 0.06493(14) 0.2374(3) 0.52808(13) 0.0310(8) Uani 1 1 d . . . C25 C 0.13386(14) 0.2095(3) 0.54358(12) 0.0265(7) Uani 1 1 d . B . C26 C 0.17207(14) 0.2868(3) 0.57796(12) 0.0287(8) Uani 1 1 d . . . H26 H 0.1529 0.3508 0.5923 0.034 Uiso 1 1 calc R B . C27 C 0.23544(14) 0.2770(3) 0.59264(11) 0.0238(7) Uani 1 1 d . B . C28 C 0.27085(14) 0.3719(3) 0.62609(11) 0.0223(7) Uani 1 1 d . . . C29 C 0.33086(14) 0.3451(3) 0.64958(11) 0.0217(7) Uani 1 1 d . B . H29 H 0.3468 0.2666 0.6452 0.026 Uiso 1 1 calc R . . C30 C 0.36791(14) 0.4297(3) 0.67914(11) 0.0233(7) Uani 1 1 d . . . C31 C 0.34395(14) 0.5449(3) 0.68485(12) 0.0299(8) Uani 1 1 d . B . H31 H 0.3686 0.6047 0.7045 0.036 Uiso 1 1 calc R . . C32 C 0.28497(16) 0.5723(3) 0.66217(13) 0.0364(9) Uani 1 1 d . . . H32 H 0.2692 0.6510 0.6665 0.044 Uiso 1 1 calc R B . C33 C 0.24819(15) 0.4876(3) 0.63317(13) 0.0323(8) Uani 1 1 d . B . H33 H 0.2074 0.5080 0.6180 0.039 Uiso 1 1 calc R . . C34 C 0.43207(14) 0.3921(3) 0.70320(11) 0.0238(7) Uani 1 1 d . A . C35 C 0.46491(14) 0.4610(3) 0.74276(11) 0.0273(7) Uani 1 1 d . . . H35 H 0.4452 0.5300 0.7532 0.033 Uiso 1 1 calc R B . C36 C 0.52460(15) 0.4360(3) 0.76817(12) 0.0270(8) Uani 1 1 d . A . C37 C 0.55747(15) 0.5233(3) 0.80917(12) 0.0324(8) Uani 1 1 d . . . C38 C 0.56201(19) 0.4583(4) 0.85908(13) 0.0507(10) Uani 1 1 d . B . H38A H 0.5836 0.3807 0.8586 0.076 Uiso 1 1 calc R . . H38B H 0.5209 0.4428 0.8647 0.076 Uiso 1 1 calc R . . H38C H 0.5844 0.5098 0.8859 0.076 Uiso 1 1 calc R . . C39 C 0.62144(17) 0.5461(4) 0.80031(15) 0.0493(10) Uani 1 1 d . B . H39A H 0.6187 0.5895 0.7688 0.074 Uiso 1 1 calc R . . H39B H 0.6423 0.4680 0.7990 0.074 Uiso 1 1 calc R . . H39C H 0.6445 0.5956 0.8275 0.074 Uiso 1 1 calc R . . C40 C 0.52523(18) 0.6453(3) 0.81059(15) 0.0526(11) Uani 1 1 d . B . H40A H 0.5503 0.6983 0.8354 0.079 Uiso 1 1 calc R . . H40B H 0.4856 0.6318 0.8195 0.079 Uiso 1 1 calc R . . H40C H 0.5191 0.6839 0.7778 0.079 Uiso 1 1 calc R . . C41 C 0.26612(19) 0.0208(3) 0.43972(13) 0.0462(10) Uani 1 1 d . . . H41A H 0.2246 -0.0091 0.4252 0.055 Uiso 1 1 calc R . . H41B H 0.2908 -0.0499 0.4546 0.055 Uiso 1 1 calc R . . C42 C 0.2940(2) 0.0730(4) 0.39849(15) 0.0617(13) Uani 1 1 d . . . H42A H 0.2922 0.0113 0.3719 0.074 Uiso 1 1 calc R . . H42B H 0.3374 0.0929 0.4118 0.074 Uiso 1 1 calc R . . C43 C 0.2602(2) 0.1874(4) 0.37676(14) 0.0586(12) Uani 1 1 d . . . H43A H 0.2819 0.2254 0.3527 0.070 Uiso 1 1 calc R . . H43B H 0.2186 0.1654 0.3588 0.070 Uiso 1 1 calc R . . C44 C 0.2562(2) 0.2770(3) 0.41764(14) 0.0537(11) Uani 1 1 d . . . H44A H 0.2975 0.3080 0.4323 0.064 Uiso 1 1 calc R . . H44B H 0.2307 0.3471 0.4035 0.064 Uiso 1 1 calc R . . C45 C 0.22938(18) 0.2187(3) 0.45762(13) 0.0415(9) Uani 1 1 d . . . H45A H 0.2294 0.2789 0.4845 0.050 Uiso 1 1 calc R . . H45B H 0.1864 0.1967 0.4436 0.050 Uiso 1 1 calc R . . C46 C 0.15564(17) -0.0931(4) 0.60768(15) 0.0496(10) Uani 1 1 d . . . H46A H 0.1662 -0.1750 0.5969 0.059 Uiso 1 1 calc R . . H46B H 0.1228 -0.0601 0.5812 0.059 Uiso 1 1 calc R . . C47 C 0.1312(2) -0.1070(4) 0.65363(17) 0.0655(13) Uani 1 1 d . . . H47A H 0.1091 -0.0316 0.6588 0.079 Uiso 1 1 calc R . . H47B H 0.1014 -0.1748 0.6488 0.079 Uiso 1 1 calc R . . C48 C 0.1779(2) -0.1313(4) 0.69878(16) 0.0660(13) Uani 1 1 d . . . H48A H 0.1902 -0.2180 0.6988 0.079 Uiso 1 1 calc R . . H48B H 0.1599 -0.1177 0.7283 0.079 Uiso 1 1 calc R . . C49 C 0.2331(2) -0.0539(5) 0.70308(15) 0.0749(15) Uani 1 1 d . . . H49A H 0.2664 -0.0906 0.7281 0.090 Uiso 1 1 calc R . . H49B H 0.2242 0.0273 0.7156 0.090 Uiso 1 1 calc R . . C50 C 0.25512(18) -0.0369(5) 0.65588(13) 0.0580(12) Uani 1 1 d . . . H50A H 0.2838 0.0327 0.6603 0.070 Uiso 1 1 calc R . . H50B H 0.2783 -0.1105 0.6503 0.070 Uiso 1 1 calc R . . C51 C 0.61316(17) 0.2109(3) 0.63736(15) 0.0464(10) Uani 1 1 d . . . H51A H 0.5952 0.1295 0.6283 0.056 Uiso 1 1 calc R . . H51B H 0.6491 0.1998 0.6648 0.056 Uiso 1 1 calc R . . C52 C 0.63428(19) 0.2639(4) 0.59276(15) 0.0538(11) Uani 1 1 d . . . H52A H 0.6677 0.2130 0.5852 0.065 Uiso 1 1 calc R . . H52B H 0.6001 0.2621 0.5635 0.065 Uiso 1 1 calc R . . C53 C 0.65620(18) 0.3918(4) 0.60206(15) 0.0528(11) Uani 1 1 d . . . H53A H 0.6638 0.4272 0.5708 0.063 Uiso 1 1 calc R . . H53B H 0.6952 0.3918 0.6268 0.063 Uiso 1 1 calc R . . C54 C 0.61055(19) 0.4692(3) 0.62094(14) 0.0488(10) Uani 1 1 d . . . H54A H 0.5744 0.4819 0.5939 0.059 Uiso 1 1 calc R . . H54B H 0.6288 0.5499 0.6309 0.059 Uiso 1 1 calc R . . C55 C 0.59081(16) 0.4106(3) 0.66491(13) 0.0373(9) Uani 1 1 d . . . H55A H 0.6259 0.4096 0.6935 0.045 Uiso 1 1 calc R . . H55B H 0.5583 0.4609 0.6743 0.045 Uiso 1 1 calc R . . C56 C 0.42325(18) 0.0874(4) 0.75238(17) 0.0651(13) Uani 1 1 d . . . H56A H 0.4135 0.0532 0.7183 0.078 Uiso 1 1 calc R . . H56B H 0.4013 0.1659 0.7517 0.078 Uiso 1 1 calc R . . C57 C 0.3997(2) 0.0015(6) 0.7868(2) 0.102(2) Uani 1 1 d . . . H57A H 0.3546 0.0059 0.7795 0.123 Uiso 1 1 calc R . . H57B H 0.4112 -0.0828 0.7796 0.123 Uiso 1 1 calc R . . C58 C 0.4224(3) 0.0260(6) 0.8400(2) 0.0970(19) Uani 1 1 d . . . H58A H 0.4130 -0.0449 0.8594 0.116 Uiso 1 1 calc R . . H58B H 0.4004 0.0974 0.8497 0.116 Uiso 1 1 calc R . . C59 C 0.4890(2) 0.0502(4) 0.85337(17) 0.0693(14) Uani 1 1 d . . . H59A H 0.5113 -0.0278 0.8536 0.083 Uiso 1 1 calc R . . H59B H 0.4993 0.0847 0.8874 0.083 Uiso 1 1 calc R . . C60 C 0.5099(2) 0.1371(4) 0.81787(14) 0.0568(11) Uani 1 1 d . . . H60A H 0.4965 0.2203 0.8246 0.068 Uiso 1 1 calc R . . H60B H 0.5551 0.1371 0.8249 0.068 Uiso 1 1 calc R . . C61 C 0.4432(3) 0.1347(6) 0.5348(2) 0.0585(7) Uani 0.75 1 d PD C 1 H61A H 0.4359 0.0459 0.5309 0.070 Uiso 0.75 1 calc PR C 1 H61B H 0.4731 0.1485 0.5663 0.070 Uiso 0.75 1 calc PR C 1 C62 C 0.4695(4) 0.1832(5) 0.4907(3) 0.0585(7) Uani 0.75 1 d PD C 1 H62A H 0.4425 0.1603 0.4587 0.070 Uiso 0.75 1 calc PR C 1 H62B H 0.5105 0.1484 0.4917 0.070 Uiso 0.75 1 calc PR C 1 C64 C 0.4177(3) 0.3881(7) 0.5057(3) 0.0585(7) Uani 0.75 1 d PD C 1 H64A H 0.3854 0.3830 0.4751 0.070 Uiso 0.75 1 calc PR C 1 H64B H 0.4251 0.4754 0.5139 0.070 Uiso 0.75 1 calc PR C 1 C65 C 0.3963(4) 0.3284(7) 0.5465(3) 0.0585(7) Uani 0.75 1 d PD C 1 H65A H 0.4264 0.3409 0.5780 0.070 Uiso 0.75 1 calc PR C 1 H65B H 0.3571 0.3652 0.5503 0.070 Uiso 0.75 1 calc PR C 1 C63 C 0.4736(3) 0.3333(5) 0.4962(2) 0.0585(7) Uani 0.75 1 d PD C 1 H63A H 0.5079 0.3545 0.5239 0.070 Uiso 0.75 1 calc PR C 1 H63B H 0.4824 0.3684 0.4653 0.070 Uiso 0.75 1 calc PR C 1 C61A C 0.4101(11) 0.314(2) 0.5515(10) 0.053(2) Uiso 0.25 1 d PD D 2 H61C H 0.3711 0.2736 0.5366 0.064 Uiso 0.25 1 calc PR D 2 H61D H 0.4023 0.3758 0.5758 0.064 Uiso 0.25 1 calc PR D 2 C62A C 0.4383(9) 0.375(2) 0.5107(9) 0.053(2) Uiso 0.25 1 d PD D 2 H62C H 0.4799 0.4048 0.5251 0.064 Uiso 0.25 1 calc PR D 2 H62D H 0.4131 0.4451 0.4960 0.064 Uiso 0.25 1 calc PR D 2 C63A C 0.4406(8) 0.2751(16) 0.4695(6) 0.053(2) Uiso 0.25 1 d PD D 2 H63C H 0.4016 0.2300 0.4608 0.064 Uiso 0.25 1 calc PR D 2 H63D H 0.4492 0.3128 0.4389 0.064 Uiso 0.25 1 calc PR D 2 C65A C 0.4720(10) 0.2242(18) 0.4841(8) 0.053(2) Uiso 0.25 1 d PD D 2 H65C H 0.5071 0.2746 0.5006 0.064 Uiso 0.25 1 calc PR D 2 H65D H 0.4852 0.1756 0.4579 0.064 Uiso 0.25 1 calc PR D 2 C64A C 0.4554(9) 0.1410(19) 0.5209(7) 0.053(2) Uiso 0.25 1 d PD D 2 H64C H 0.4143 0.1065 0.5081 0.064 Uiso 0.25 1 calc PR D 2 H64D H 0.4850 0.0730 0.5278 0.064 Uiso 0.25 1 calc PR D 2 N1 N 0.26238(12) 0.1088(2) 0.47919(10) 0.0278(6) Uani 1 1 d D . . H1N H 0.3006(7) 0.129(3) 0.4930(11) 0.042 Uiso 1 1 d D . . N2 N 0.20876(14) -0.0153(3) 0.61180(11) 0.0387(7) Uani 1 1 d D . . H2N H 0.1939(17) 0.0568(18) 0.6182(14) 0.058 Uiso 1 1 d D . . N3 N 0.56829(12) 0.2864(3) 0.65507(10) 0.0294(6) Uani 1 1 d D . . H3N H 0.5343(9) 0.286(3) 0.6319(9) 0.044 Uiso 1 1 d D . . N4 N 0.48813(14) 0.1109(3) 0.76571(12) 0.0416(8) Uani 1 1 d D . . H4N H 0.5031(17) 0.0363(17) 0.7637(15) 0.062 Uiso 1 1 d D . . N5 N 0.3876(2) 0.1951(4) 0.53664(17) 0.0585(7) Uani 0.75 1 d PD C 1 H5N H 0.385(3) 0.173(5) 0.5672(9) 0.088 Uiso 0.75 1 d PD E 1 N5A N 0.4559(6) 0.2243(12) 0.5757(5) 0.053(2) Uiso 0.25 1 d P D 2 O1 O 0.20052(9) -0.11501(18) 0.50863(8) 0.0293(5) Uani 1 1 d . . . O2 O 0.31711(9) -0.04402(18) 0.56385(8) 0.0254(5) Uani 1 1 d . . . O3 O 0.50193(9) 0.06121(18) 0.66727(8) 0.0286(5) Uani 1 1 d . . . O4 O 0.60704(9) 0.11941(19) 0.74057(8) 0.0287(5) Uani 1 1 d . . . O5 O 0.15159(9) 0.11617(19) 0.52474(8) 0.0299(5) Uani 1 1 d . . . O6 O 0.26763(9) 0.19246(18) 0.57976(7) 0.0255(5) Uani 1 1 d . . . O7 O 0.45118(9) 0.29770(18) 0.68454(8) 0.0273(5) Uani 1 1 d . . . O8 O 0.55571(9) 0.34506(19) 0.76083(8) 0.0291(5) Uani 1 1 d . . . Ni1 Ni 0.235020(18) 0.03835(3) 0.543093(15) 0.02421(11) Uani 1 1 d . B . Ni2 Ni 0.529075(18) 0.20693(4) 0.712512(15) 0.02479(11) Uani 1 1 d . A . 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 0.080(3) 0.038(2) 0.049(3) -0.006(2) -0.025(2) -0.011(2) C2 0.035(2) 0.0260(19) 0.057(3) -0.0127(17) 0.0062(18) -0.0031(16) C3 0.028(2) 0.040(2) 0.104(4) -0.019(2) 0.017(2) -0.0064(18) C4 0.0283(19) 0.0265(18) 0.039(2) -0.0064(16) -0.0027(16) -0.0010(15) C5 0.0284(18) 0.0259(18) 0.0232(18) -0.0018(14) 0.0066(15) -0.0015(15) C6 0.0211(17) 0.0202(16) 0.036(2) -0.0022(14) 0.0015(15) -0.0005(14) C7 0.0226(18) 0.0224(17) 0.0230(18) -0.0004(13) 0.0058(14) 0.0022(14) C8 0.0200(17) 0.0216(16) 0.0230(17) 0.0015(14) 0.0046(14) 0.0023(14) C9 0.0254(18) 0.0203(16) 0.0262(18) 0.0014(14) 0.0066(15) 0.0009(14) C10 0.0211(17) 0.0225(17) 0.0258(18) 0.0027(14) 0.0039(14) 0.0035(14) C11 0.0253(18) 0.0302(19) 0.034(2) 0.0003(16) -0.0037(16) 0.0079(15) C12 0.029(2) 0.0182(17) 0.045(2) -0.0010(16) 0.0006(17) 0.0057(15) C13 0.0272(19) 0.0222(18) 0.036(2) -0.0043(15) 0.0032(16) -0.0010(14) C14 0.0227(17) 0.0233(17) 0.0279(18) -0.0003(14) 0.0046(14) 0.0028(15) C15 0.0280(19) 0.0206(17) 0.034(2) 0.0002(14) -0.0001(16) 0.0047(14) C16 0.0230(18) 0.0268(18) 0.0254(18) 0.0041(14) 0.0046(15) 0.0020(14) C17 0.0257(18) 0.0274(18) 0.0298(19) 0.0025(15) -0.0027(15) 0.0024(15) C18 0.023(3) 0.053(5) 0.035(4) 0.008(4) -0.006(3) 0.003(3) C19 0.023(3) 0.053(5) 0.035(4) 0.008(4) -0.006(3) 0.003(3) C20 0.023(3) 0.053(5) 0.035(4) 0.008(4) -0.006(3) 0.003(3) C21 0.027(3) 0.045(3) 0.076(4) 0.010(3) -0.005(3) 0.009(2) C22 0.028(3) 0.083(4) 0.081(4) -0.040(4) -0.018(3) 0.022(3) C23 0.025(3) 0.087(4) 0.070(4) 0.035(3) 0.013(3) 0.011(3) C24 0.0170(17) 0.0288(18) 0.045(2) -0.0048(16) 0.0022(16) 0.0041(14) C25 0.0256(18) 0.0241(17) 0.0292(18) 0.0014(15) 0.0043(15) 0.0051(15) C26 0.0224(18) 0.0303(18) 0.0336(19) -0.0082(16) 0.0062(15) 0.0057(15) C27 0.0257(18) 0.0209(16) 0.0249(18) 0.0013(14) 0.0058(14) 0.0041(14) C28 0.0247(18) 0.0228(16) 0.0201(17) 0.0019(13) 0.0062(14) 0.0004(14) C29 0.0246(18) 0.0182(16) 0.0240(17) 0.0005(13) 0.0087(14) 0.0045(13) C30 0.0229(17) 0.0244(17) 0.0232(17) 0.0008(13) 0.0066(14) 0.0003(14) C31 0.0278(19) 0.0233(17) 0.035(2) -0.0086(15) -0.0012(15) -0.0001(15) C32 0.035(2) 0.0228(18) 0.050(2) -0.0089(16) 0.0037(18) 0.0064(16) C33 0.0237(18) 0.0315(19) 0.039(2) -0.0020(16) -0.0005(16) 0.0092(15) C34 0.0254(18) 0.0213(17) 0.0257(18) 0.0020(14) 0.0075(15) -0.0002(14) C35 0.0292(19) 0.0250(17) 0.0270(18) -0.0042(15) 0.0041(15) 0.0025(15) C36 0.0308(19) 0.0227(18) 0.0277(19) 0.0008(14) 0.0061(16) -0.0025(15) C37 0.031(2) 0.034(2) 0.0287(19) -0.0060(16) 0.0000(16) -0.0039(16) C38 0.063(3) 0.053(2) 0.031(2) -0.0054(19) -0.0013(19) -0.012(2) C39 0.043(2) 0.053(2) 0.049(2) -0.011(2) 0.0027(19) -0.018(2) C40 0.057(3) 0.039(2) 0.052(3) -0.019(2) -0.012(2) 0.001(2) C41 0.075(3) 0.030(2) 0.038(2) -0.0033(17) 0.021(2) 0.009(2) C42 0.101(4) 0.050(3) 0.042(3) -0.001(2) 0.032(3) 0.013(3) C43 0.085(3) 0.052(3) 0.037(2) 0.006(2) 0.010(2) 0.002(2) C44 0.077(3) 0.042(2) 0.042(2) 0.009(2) 0.013(2) 0.008(2) C45 0.055(2) 0.033(2) 0.035(2) 0.0060(17) 0.0073(19) 0.0155(19) C46 0.037(2) 0.059(3) 0.053(3) 0.006(2) 0.009(2) -0.007(2) C47 0.058(3) 0.077(3) 0.070(3) 0.014(3) 0.032(3) -0.008(3) C48 0.071(3) 0.083(3) 0.054(3) 0.013(3) 0.037(3) 0.011(3) C49 0.083(4) 0.106(4) 0.035(3) -0.001(3) 0.010(2) -0.012(3) C50 0.041(2) 0.098(4) 0.033(2) 0.011(2) 0.004(2) -0.006(2) C51 0.043(2) 0.042(2) 0.061(3) 0.005(2) 0.026(2) 0.0121(19) C52 0.053(3) 0.057(3) 0.059(3) 0.008(2) 0.031(2) 0.016(2) C53 0.040(2) 0.067(3) 0.054(3) 0.017(2) 0.017(2) 0.001(2) C54 0.054(3) 0.046(2) 0.050(3) 0.012(2) 0.019(2) -0.004(2) C55 0.036(2) 0.035(2) 0.042(2) 0.0047(17) 0.0119(18) -0.0021(17) C56 0.034(2) 0.081(3) 0.080(3) 0.017(3) 0.013(2) -0.015(2) C57 0.061(3) 0.129(5) 0.117(5) 0.051(4) 0.018(3) -0.044(3) C58 0.086(4) 0.115(5) 0.105(5) 0.040(4) 0.054(4) -0.017(4) C59 0.080(4) 0.079(3) 0.057(3) 0.016(3) 0.033(3) -0.013(3) C60 0.063(3) 0.070(3) 0.041(3) 0.002(2) 0.019(2) -0.013(2) C61 0.0719(18) 0.0546(16) 0.0565(16) 0.0122(13) 0.0304(15) -0.0083(14) C62 0.0719(18) 0.0546(16) 0.0565(16) 0.0122(13) 0.0304(15) -0.0083(14) C64 0.0719(18) 0.0546(16) 0.0565(16) 0.0122(13) 0.0304(15) -0.0083(14) C65 0.0719(18) 0.0546(16) 0.0565(16) 0.0122(13) 0.0304(15) -0.0083(14) C63 0.0719(18) 0.0546(16) 0.0565(16) 0.0122(13) 0.0304(15) -0.0083(14) N1 0.0267(16) 0.0262(15) 0.0278(16) -0.0016(12) -0.0006(13) 0.0034(13) N2 0.0376(18) 0.0418(18) 0.0359(18) 0.0017(15) 0.0058(15) -0.0063(15) N3 0.0235(15) 0.0311(15) 0.0335(17) -0.0028(14) 0.0057(13) 0.0014(13) N4 0.0349(19) 0.0470(19) 0.043(2) 0.0048(17) 0.0093(15) -0.0078(16) N5 0.0719(18) 0.0546(16) 0.0565(16) 0.0122(13) 0.0304(15) -0.0083(14) O1 0.0242(12) 0.0230(12) 0.0374(14) -0.0036(10) -0.0011(10) 0.0035(10) O2 0.0231(12) 0.0190(11) 0.0315(13) -0.0025(10) -0.0005(10) 0.0031(10) O3 0.0270(13) 0.0198(12) 0.0358(13) -0.0008(10) -0.0012(10) 0.0034(10) O4 0.0244(12) 0.0238(12) 0.0352(14) 0.0001(10) -0.0003(10) 0.0014(10) O5 0.0243(12) 0.0254(12) 0.0371(14) -0.0069(10) -0.0004(11) 0.0039(10) O6 0.0209(12) 0.0243(12) 0.0296(12) -0.0060(10) 0.0013(10) 0.0051(10) O7 0.0234(12) 0.0229(11) 0.0335(13) -0.0077(10) 0.0013(10) 0.0002(10) O8 0.0261(13) 0.0278(12) 0.0309(13) -0.0010(10) 0.0004(10) -0.0001(10) Ni1 0.0206(2) 0.0217(2) 0.0290(2) -0.00338(19) 0.00186(18) 0.00309(18) Ni2 0.0210(2) 0.0218(2) 0.0301(2) -0.00139(19) 0.00211(18) 0.00102(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 C1 C4 1.521(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.525(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.534(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.541(4) . ? C5 O1 1.258(4) . ? C5 C6 1.407(4) . ? C6 C7 1.398(4) . ? C6 H6 0.9500 . ? C7 O2 1.267(3) . ? C7 C8 1.510(4) . ? C8 C13 1.383(4) . ? C8 C9 1.393(4) . ? C9 C10 1.396(4) . ? C9 H9 0.9500 . ? C10 C11 1.394(4) . ? C10 C14 1.508(4) . ? C11 C12 1.375(4) . ? C11 H11 0.9500 . ? C12 C13 1.379(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.270(3) . ? C14 C15 1.405(4) . ? C15 C16 1.408(4) . ? C15 H15 0.9500 . ? C16 O4 1.253(3) . ? C16 C17 1.537(4) . ? C17 C20 1.497(11) . ? C17 C18A 1.47(2) . ? C17 C19B 1.509(16) . ? C17 C20B 1.53(2) . ? C17 C20A 1.55(3) . ? C17 C18 1.543(12) . ? C17 C19 1.554(10) . ? C17 C18B 1.563(17) . ? C17 C19A 1.57(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C18A H18D 0.9800 . ? C18A H18E 0.9800 . ? C18A H18F 0.9800 . ? C19A H19D 0.9800 . ? C19A H19E 0.9800 . ? C19A H19F 0.9800 . ? C20A H20D 0.9800 . ? C20A H20E 0.9800 . ? C20A H20F 0.9800 . ? C18B H18G 0.9800 . ? C18B H18H 0.9800 . ? C18B H18I 0.9800 . ? C19B H19G 0.9800 . ? C19B H19H 0.9800 . ? C19B H19I 0.9800 . ? C20B H20G 0.9800 . ? C20B H20H 0.9800 . ? C20B H20I 0.9800 . ? C21 C24 1.503(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.533(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.504(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C21A C24 1.509(17) . ? C21A H21D 0.9800 . ? C21A H21E 0.9800 . ? C21A H21F 0.9800 . ? C22A C24 1.50(2) . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A C24 1.591(18) . ? C23A H23D 0.9800 . ? C23A H23E 0.9800 . ? C23A H23F 0.9800 . ? C24 C25 1.546(4) . ? C25 O5 1.249(3) . ? C25 C26 1.417(4) . ? C26 C27 1.398(4) . ? C26 H26 0.9500 . ? C27 O6 1.269(3) . ? C27 C28 1.503(4) . ? C28 C33 1.395(4) . ? C28 C29 1.397(4) . ? C29 C30 1.389(4) . ? C29 H29 0.9500 . ? C30 C31 1.396(4) . ? C30 C34 1.510(4) . ? C31 C32 1.372(4) . ? C31 H31 0.9500 . ? C32 C33 1.381(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 O7 1.269(3) . ? C34 C35 1.401(4) . ? C35 C36 1.401(4) . ? C35 H35 0.9500 . ? C36 O8 1.258(4) . ? C36 C37 1.544(4) . ? C37 C39 1.524(5) . ? C37 C40 1.525(5) . ? C37 C38 1.531(5) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 N1 1.468(4) . ? C41 C42 1.516(5) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.522(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.510(5) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.501(5) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 N1 1.474(4) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 N2 1.450(4) . ? C46 C47 1.485(5) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.473(6) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C49 1.484(6) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C50 1.493(5) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 N2 1.442(5) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 N3 1.462(4) . ? C51 C52 1.519(5) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.491(5) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.503(5) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.514(5) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 N3 1.459(4) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 N4 1.447(5) . ? C56 C57 1.507(6) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 C58 1.471(7) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 C59 1.485(7) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C59 C60 1.507(5) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60 N4 1.444(5) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C61 N5 1.423(8) . ? C61 C62 1.547(7) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C62 C63 1.655(8) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C64 C63 1.462(8) . ? C64 C65 1.464(10) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 N5 1.492(10) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C61A C62A 1.55(3) . ? C61A N5A 1.48(2) . ? C61A H61C 0.9900 . ? C61A H61D 0.9900 . ? C62A C63A 1.59(3) . ? C62A H62C 0.9900 . ? C62A H62D 0.9900 . ? C63A C65A 0.92(2) . ? C63A H63C 0.9900 . ? C63A H63D 0.9900 . ? C65A C64A 1.47(2) . ? C65A H65C 0.9900 . ? C65A H65D 0.9900 . ? C64A N5A 1.76(2) . ? C64A H64C 0.9900 . ? C64A H64D 0.9900 . ? N1 Ni1 2.123(3) . ? N1 H1N 0.891(10) . ? N2 Ni1 2.173(3) . ? N2 H2N 0.889(10) . ? N3 Ni2 2.145(3) . ? N3 H3N 0.886(10) . ? N4 Ni2 2.156(3) . ? N4 H4N 0.890(10) . ? N5 H5N 0.888(10) . ? O1 Ni1 2.005(2) . ? O2 Ni1 2.023(2) . ? O3 Ni2 2.039(2) . ? O4 Ni2 2.002(2) . ? O5 Ni1 2.022(2) . ? O6 Ni1 2.026(2) . ? O7 Ni2 2.018(2) . ? O8 Ni2 2.022(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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 C2 110.0(3) . . ? C1 C4 C3 108.9(3) . . ? C2 C4 C3 108.5(3) . . ? C1 C4 C5 107.2(3) . . ? C2 C4 C5 115.0(3) . . ? C3 C4 C5 107.1(3) . . ? O1 C5 C6 125.3(3) . . ? O1 C5 C4 114.0(3) . . ? C6 C5 C4 120.7(3) . . ? C7 C6 C5 125.4(3) . . ? C7 C6 H6 117.3 . . ? C5 C6 H6 117.3 . . ? O2 C7 C6 125.3(3) . . ? O2 C7 C8 115.3(3) . . ? C6 C7 C8 119.4(3) . . ? C13 C8 C9 118.4(3) . . ? C13 C8 C7 123.1(3) . . ? C9 C8 C7 118.5(3) . . ? C8 C9 C10 122.0(3) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C11 C10 C9 117.8(3) . . ? C11 C10 C14 123.9(3) . . ? C9 C10 C14 118.3(3) . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C8 120.4(3) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? O3 C14 C15 124.9(3) . . ? O3 C14 C10 115.0(3) . . ? C15 C14 C10 120.1(3) . . ? C14 C15 C16 125.3(3) . . ? C14 C15 H15 117.3 . . ? C16 C15 H15 117.3 . . ? O4 C16 C15 125.0(3) . . ? O4 C16 C17 114.3(3) . . ? C15 C16 C17 120.7(3) . . ? C20 C17 C18A 118.9(9) . . ? C18A C17 C19B 130.9(11) . . ? C20 C17 C20B 91.8(9) . . ? C19B C17 C20B 111.4(9) . . ? C20 C17 C20A 91.6(9) . . ? C18A C17 C20A 111.4(11) . . ? C19B C17 C20A 70.9(10) . . ? C20B C17 C20A 142.9(13) . . ? C20 C17 C16 115.0(5) . . ? C18A C17 C16 111.2(9) . . ? C19B C17 C16 114.9(7) . . ? C20B C17 C16 105.7(8) . . ? C20A C17 C16 106.2(10) . . ? C20 C17 C18 108.4(7) . . ? C19B C17 C18 125.2(8) . . ? C20A C17 C18 127.4(10) . . ? C16 C17 C18 107.8(5) . . ? C20 C17 C19 109.9(7) . . ? C18A C17 C19 94.4(8) . . ? C19B C17 C19 89.9(7) . . ? C20B C17 C19 130.3(9) . . ? C16 C17 C19 104.4(4) . . ? C18 C17 C19 111.3(7) . . ? C20 C17 C18B 124.7(8) . . ? C18A C17 C18B 71.3(9) . . ? C19B C17 C18B 108.2(8) . . ? C20B C17 C18B 108.3(9) . . ? C16 C17 C18B 108.2(7) . . ? C18 C17 C18B 88.5(8) . . ? C18A C17 C19A 106.0(10) . . ? C20B C17 C19A 75.1(10) . . ? C20A C17 C19A 108.2(11) . . ? C16 C17 C19A 113.9(8) . . ? C18 C17 C19A 93.1(9) . . ? C19 C17 C19A 125.1(8) . . ? C18B C17 C19A 135.1(11) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? C17 C18A H18D 109.5 . . ? C17 C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17 C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? C17 C19A H19D 109.5 . . ? C17 C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C17 C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C17 C20A H20D 109.5 . . ? C17 C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C17 C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? C17 C18B H18G 109.5 . . ? C17 C18B H18H 109.5 . . ? C17 C18B H18I 109.5 . . ? C17 C19B H19G 109.5 . . ? C17 C19B H19H 109.5 . . ? C17 C19B H19I 109.5 . . ? C17 C20B H20G 109.5 . . ? C17 C20B H20H 109.5 . . ? C17 C20B H20I 109.5 . . ? C24 C21 H21A 109.5 . . ? C24 C21 H21B 109.5 . . ? C24 C21 H21C 109.5 . . ? C24 C22 H22A 109.5 . . ? C24 C22 H22B 109.5 . . ? C24 C22 H22C 109.5 . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C24 C23 H23C 109.5 . . ? C24 C21A H21D 109.5 . . ? C24 C21A H21E 109.5 . . ? H21D C21A H21E 109.5 . . ? C24 C21A H21F 109.5 . . ? H21D C21A H21F 109.5 . . ? H21E C21A H21F 109.5 . . ? C24 C22A H22D 109.5 . . ? C24 C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? C24 C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? C24 C23A H23D 109.5 . . ? C24 C23A H23E 109.5 . . ? H23D C23A H23E 109.5 . . ? C24 C23A H23F 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? C22A C24 C21 141.0(9) . . ? C22A C24 C23 47.8(8) . . ? C21 C24 C23 110.6(4) . . ? C22A C24 C21A 115.8(12) . . ? C21 C24 C21A 61.0(7) . . ? C23 C24 C21A 146.0(8) . . ? C22A C24 C22 64.3(9) . . ? C21 C24 C22 108.3(4) . . ? C23 C24 C22 108.7(4) . . ? C21A C24 C22 52.9(7) . . ? C22A C24 C25 105.9(8) . . ? C21 C24 C25 112.3(3) . . ? C23 C24 C25 107.7(3) . . ? C21A C24 C25 105.6(7) . . ? C22 C24 C25 109.1(3) . . ? C22A C24 C23A 107.6(11) . . ? C21 C24 C23A 49.4(7) . . ? C23 C24 C23A 63.2(7) . . ? C21A C24 C23A 108.2(10) . . ? C22 C24 C23A 136.5(7) . . ? C25 C24 C23A 114.0(7) . . ? O5 C25 C26 124.5(3) . . ? O5 C25 C24 115.7(3) . . ? C26 C25 C24 119.7(3) . . ? C27 C26 C25 125.7(3) . . ? C27 C26 H26 117.2 . . ? C25 C26 H26 117.2 . . ? O6 C27 C26 125.3(3) . . ? O6 C27 C28 114.7(3) . . ? C26 C27 C28 119.9(3) . . ? C33 C28 C29 118.1(3) . . ? C33 C28 C27 123.7(3) . . ? C29 C28 C27 118.2(3) . . ? C30 C29 C28 122.0(3) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C31 118.3(3) . . ? C29 C30 C34 118.2(3) . . ? C31 C30 C34 123.5(3) . . ? C32 C31 C30 120.3(3) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C31 C32 C33 121.2(3) . . ? C31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? C32 C33 C28 120.1(3) . . ? C32 C33 H33 119.9 . . ? C28 C33 H33 119.9 . . ? O7 C34 C35 126.0(3) . . ? O7 C34 C30 114.6(3) . . ? C35 C34 C30 119.4(3) . . ? C36 C35 C34 125.0(3) . . ? C36 C35 H35 117.5 . . ? C34 C35 H35 117.5 . . ? O8 C36 C35 125.4(3) . . ? O8 C36 C37 114.4(3) . . ? C35 C36 C37 120.2(3) . . ? C39 C37 C40 109.0(3) . . ? C39 C37 C38 109.3(3) . . ? C40 C37 C38 109.2(3) . . ? C39 C37 C36 107.9(3) . . ? C40 C37 C36 113.9(3) . . ? C38 C37 C36 107.4(3) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? N1 C41 C42 113.6(3) . . ? N1 C41 H41A 108.8 . . ? C42 C41 H41A 108.8 . . ? N1 C41 H41B 108.8 . . ? C42 C41 H41B 108.8 . . ? H41A C41 H41B 107.7 . . ? C41 C42 C43 110.9(3) . . ? C41 C42 H42A 109.5 . . ? C43 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? C43 C42 H42B 109.5 . . ? H42A C42 H42B 108.1 . . ? C44 C43 C42 110.3(3) . . ? C44 C43 H43A 109.6 . . ? C42 C43 H43A 109.6 . . ? C44 C43 H43B 109.6 . . ? C42 C43 H43B 109.6 . . ? H43A C43 H43B 108.1 . . ? C45 C44 C43 111.2(3) . . ? C45 C44 H44A 109.4 . . ? C43 C44 H44A 109.4 . . ? C45 C44 H44B 109.4 . . ? C43 C44 H44B 109.4 . . ? H44A C44 H44B 108.0 . . ? N1 C45 C44 113.5(3) . . ? N1 C45 H45A 108.9 . . ? C44 C45 H45A 108.9 . . ? N1 C45 H45B 108.9 . . ? C44 C45 H45B 108.9 . . ? H45A C45 H45B 107.7 . . ? N2 C46 C47 115.8(3) . . ? N2 C46 H46A 108.3 . . ? C47 C46 H46A 108.3 . . ? N2 C46 H46B 108.3 . . ? C47 C46 H46B 108.3 . . ? H46A C46 H46B 107.4 . . ? C48 C47 C46 114.3(4) . . ? C48 C47 H47A 108.7 . . ? C46 C47 H47A 108.7 . . ? C48 C47 H47B 108.7 . . ? C46 C47 H47B 108.7 . . ? H47A C47 H47B 107.6 . . ? C47 C48 C49 113.5(4) . . ? C47 C48 H48A 108.9 . . ? C49 C48 H48A 108.9 . . ? C47 C48 H48B 108.9 . . ? C49 C48 H48B 108.9 . . ? H48A C48 H48B 107.7 . . ? C48 C49 C50 115.0(4) . . ? C48 C49 H49A 108.5 . . ? C50 C49 H49A 108.5 . . ? C48 C49 H49B 108.5 . . ? C50 C49 H49B 108.5 . . ? H49A C49 H49B 107.5 . . ? N2 C50 C49 116.1(3) . . ? N2 C50 H50A 108.3 . . ? C49 C50 H50A 108.3 . . ? N2 C50 H50B 108.3 . . ? C49 C50 H50B 108.3 . . ? H50A C50 H50B 107.4 . . ? N3 C51 C52 113.8(3) . . ? N3 C51 H51A 108.8 . . ? C52 C51 H51A 108.8 . . ? N3 C51 H51B 108.8 . . ? C52 C51 H51B 108.8 . . ? H51A C51 H51B 107.7 . . ? C53 C52 C51 111.6(3) . . ? C53 C52 H52A 109.3 . . ? C51 C52 H52A 109.3 . . ? C53 C52 H52B 109.3 . . ? C51 C52 H52B 109.3 . . ? H52A C52 H52B 108.0 . . ? C52 C53 C54 111.6(3) . . ? C52 C53 H53A 109.3 . . ? C54 C53 H53A 109.3 . . ? C52 C53 H53B 109.3 . . ? C54 C53 H53B 109.3 . . ? H53A C53 H53B 108.0 . . ? C53 C54 C55 111.6(3) . . ? C53 C54 H54A 109.3 . . ? C55 C54 H54A 109.3 . . ? C53 C54 H54B 109.3 . . ? C55 C54 H54B 109.3 . . ? H54A C54 H54B 108.0 . . ? N3 C55 C54 113.3(3) . . ? N3 C55 H55A 108.9 . . ? C54 C55 H55A 108.9 . . ? N3 C55 H55B 108.9 . . ? C54 C55 H55B 108.9 . . ? H55A C55 H55B 107.7 . . ? N4 C56 C57 114.7(4) . . ? N4 C56 H56A 108.6 . . ? C57 C56 H56A 108.6 . . ? N4 C56 H56B 108.6 . . ? C57 C56 H56B 108.6 . . ? H56A C56 H56B 107.6 . . ? C58 C57 C56 114.6(5) . . ? C58 C57 H57A 108.6 . . ? C56 C57 H57A 108.6 . . ? C58 C57 H57B 108.6 . . ? C56 C57 H57B 108.6 . . ? H57A C57 H57B 107.6 . . ? C57 C58 C59 113.6(4) . . ? C57 C58 H58A 108.8 . . ? C59 C58 H58A 108.8 . . ? C57 C58 H58B 108.8 . . ? C59 C58 H58B 108.8 . . ? H58A C58 H58B 107.7 . . ? C58 C59 C60 112.6(4) . . ? C58 C59 H59A 109.1 . . ? C60 C59 H59A 109.1 . . ? C58 C59 H59B 109.1 . . ? C60 C59 H59B 109.1 . . ? H59A C59 H59B 107.8 . . ? N4 C60 C59 115.5(4) . . ? N4 C60 H60A 108.4 . . ? C59 C60 H60A 108.4 . . ? N4 C60 H60B 108.4 . . ? C59 C60 H60B 108.4 . . ? H60A C60 H60B 107.5 . . ? N5 C61 C62 110.3(5) . . ? N5 C61 H61A 109.6 . . ? C62 C61 H61A 109.6 . . ? N5 C61 H61B 109.6 . . ? C62 C61 H61B 109.6 . . ? H61A C61 H61B 108.1 . . ? C61 C62 C63 107.0(5) . . ? C61 C62 H62A 110.3 . . ? C63 C62 H62A 110.3 . . ? C61 C62 H62B 110.3 . . ? C63 C62 H62B 110.3 . . ? H62A C62 H62B 108.6 . . ? C63 C64 C65 112.4(5) . . ? C63 C64 H64A 109.1 . . ? C65 C64 H64A 109.1 . . ? C63 C64 H64B 109.1 . . ? C65 C64 H64B 109.1 . . ? H64A C64 H64B 107.8 . . ? N5 C65 C64 110.5(7) . . ? N5 C65 H65A 109.5 . . ? C64 C65 H65A 109.5 . . ? N5 C65 H65B 109.5 . . ? C64 C65 H65B 109.5 . . ? H65A C65 H65B 108.1 . . ? C64 C63 C62 113.1(5) . . ? C64 C63 H63A 109.0 . . ? C62 C63 H63A 109.0 . . ? C64 C63 H63B 109.0 . . ? C62 C63 H63B 109.0 . . ? H63A C63 H63B 107.8 . . ? C62A C61A N5A 105.3(17) . . ? C62A C61A H61C 110.7 . . ? N5A C61A H61C 110.7 . . ? C62A C61A H61D 110.7 . . ? N5A C61A H61D 110.7 . . ? H61C C61A H61D 108.8 . . ? C61A C62A C63A 107.5(18) . . ? C61A C62A H62C 110.2 . . ? C63A C62A H62C 110.2 . . ? C61A C62A H62D 110.2 . . ? C63A C62A H62D 110.2 . . ? H62C C62A H62D 108.5 . . ? C65A C63A C62A 104(2) . . ? C65A C63A H63C 111.0 . . ? C62A C63A H63C 111.0 . . ? C65A C63A H63D 111.0 . . ? C62A C63A H63D 111.0 . . ? H63C C63A H63D 109.0 . . ? C63A C65A C64A 113(2) . . ? C63A C65A H65C 108.9 . . ? C64A C65A H65C 108.9 . . ? C63A C65A H65D 108.9 . . ? C64A C65A H65D 108.9 . . ? H65C C65A H65D 107.7 . . ? N5A C64A C65A 108.0(15) . . ? N5A C64A H64C 110.1 . . ? C65A C64A H64C 110.1 . . ? N5A C64A H64D 110.1 . . ? C65A C64A H64D 110.1 . . ? H64C C64A H64D 108.4 . . ? C41 N1 C45 110.0(3) . . ? C41 N1 Ni1 116.3(2) . . ? C45 N1 Ni1 115.1(2) . . ? C41 N1 H1N 106(2) . . ? C45 N1 H1N 109(2) . . ? Ni1 N1 H1N 99(2) . . ? C50 N2 C46 113.9(3) . . ? C50 N2 Ni1 119.8(2) . . ? C46 N2 Ni1 117.2(2) . . ? C50 N2 H2N 102(3) . . ? C46 N2 H2N 102(3) . . ? Ni1 N2 H2N 96(3) . . ? C55 N3 C51 110.8(3) . . ? C55 N3 Ni2 115.0(2) . . ? C51 N3 Ni2 115.5(2) . . ? C55 N3 H3N 111(2) . . ? C51 N3 H3N 108(2) . . ? Ni2 N3 H3N 96(2) . . ? C60 N4 C56 113.7(3) . . ? C60 N4 Ni2 118.2(2) . . ? C56 N4 Ni2 117.5(2) . . ? C60 N4 H4N 101(3) . . ? C56 N4 H4N 101(3) . . ? Ni2 N4 H4N 101(3) . . ? C65 N5 C61 112.4(5) . . ? C65 N5 H5N 98(4) . . ? C61 N5 H5N 97(4) . . ? C64A N5A C61A 94.6(14) . . ? C5 O1 Ni1 126.7(2) . . ? C7 O2 Ni1 125.55(19) . . ? C14 O3 Ni2 124.9(2) . . ? C16 O4 Ni2 127.3(2) . . ? C25 O5 Ni1 126.9(2) . . ? C27 O6 Ni1 125.53(19) . . ? C34 O7 Ni2 125.9(2) . . ? C36 O8 Ni2 127.0(2) . . ? O1 Ni1 O5 89.47(8) . . ? O1 Ni1 O2 89.84(8) . . ? O5 Ni1 O2 177.38(9) . . ? O1 Ni1 O6 177.77(9) . . ? O5 Ni1 O6 89.49(8) . . ? O2 Ni1 O6 91.12(8) . . ? O1 Ni1 N1 93.65(10) . . ? O5 Ni1 N1 92.92(10) . . ? O2 Ni1 N1 89.65(9) . . ? O6 Ni1 N1 88.37(9) . . ? O1 Ni1 N2 92.06(10) . . ? O5 Ni1 N2 85.87(10) . . ? O2 Ni1 N2 91.63(10) . . ? O6 Ni1 N2 85.90(10) . . ? N1 Ni1 N2 174.15(11) . . ? O4 Ni2 O7 179.09(9) . . ? O4 Ni2 O8 89.51(9) . . ? O7 Ni2 O8 89.68(8) . . ? O4 Ni2 O3 89.13(8) . . ? O7 Ni2 O3 91.70(8) . . ? O8 Ni2 O3 176.62(9) . . ? O4 Ni2 N3 91.16(9) . . ? O7 Ni2 N3 88.47(9) . . ? O8 Ni2 N3 93.95(10) . . ? O3 Ni2 N3 89.17(10) . . ? O4 Ni2 N4 87.97(10) . . ? O7 Ni2 N4 92.48(10) . . ? O8 Ni2 N4 91.70(10) . . ? O3 Ni2 N4 85.16(11) . . ? N3 Ni2 N4 174.27(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C4 C5 O1 54.7(4) . . . . ? C2 C4 C5 O1 177.4(3) . . . . ? C3 C4 C5 O1 -62.0(4) . . . . ? C1 C4 C5 C6 -125.5(3) . . . . ? C2 C4 C5 C6 -2.8(4) . . . . ? C3 C4 C5 C6 117.8(3) . . . . ? O1 C5 C6 C7 -3.9(5) . . . . ? C4 C5 C6 C7 176.3(3) . . . . ? C5 C6 C7 O2 -0.5(5) . . . . ? C5 C6 C7 C8 177.8(3) . . . . ? O2 C7 C8 C13 -178.7(3) . . . . ? C6 C7 C8 C13 2.8(4) . . . . ? O2 C7 C8 C9 3.1(4) . . . . ? C6 C7 C8 C9 -175.4(3) . . . . ? C13 C8 C9 C10 0.7(4) . . . . ? C7 C8 C9 C10 179.0(3) . . . . ? C8 C9 C10 C11 -0.4(5) . . . . ? C8 C9 C10 C14 -179.0(3) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C14 C10 C11 C12 178.1(3) . . . . ? C10 C11 C12 C13 0.8(5) . . . . ? C11 C12 C13 C8 -0.4(5) . . . . ? C9 C8 C13 C12 -0.3(5) . . . . ? C7 C8 C13 C12 -178.5(3) . . . . ? C11 C10 C14 O3 176.7(3) . . . . ? C9 C10 C14 O3 -4.8(4) . . . . ? C11 C10 C14 C15 -4.5(5) . . . . ? C9 C10 C14 C15 174.0(3) . . . . ? O3 C14 C15 C16 1.4(5) . . . . ? C10 C14 C15 C16 -177.3(3) . . . . ? C14 C15 C16 O4 4.1(5) . . . . ? C14 C15 C16 C17 -178.2(3) . . . . ? O4 C16 C17 C20 -170.8(6) . . . . ? C15 C16 C17 C20 11.2(7) . . . . ? O4 C16 C17 C18A -31.9(8) . . . . ? C15 C16 C17 C18A 150.2(7) . . . . ? O4 C16 C17 C19B 165.5(6) . . . . ? C15 C16 C17 C19B -12.5(7) . . . . ? O4 C16 C17 C20B -71.2(8) . . . . ? C15 C16 C17 C20B 110.8(8) . . . . ? O4 C16 C17 C20A 89.5(9) . . . . ? C15 C16 C17 C20A -88.5(9) . . . . ? O4 C16 C17 C18 -49.8(7) . . . . ? C15 C16 C17 C18 132.3(6) . . . . ? O4 C16 C17 C19 68.7(6) . . . . ? C15 C16 C17 C19 -109.3(6) . . . . ? O4 C16 C17 C18B 44.6(7) . . . . ? C15 C16 C17 C18B -133.4(7) . . . . ? O4 C16 C17 C19A -151.6(8) . . . . ? C15 C16 C17 C19A 30.5(8) . . . . ? C22A C24 C25 O5 51.2(10) . . . . ? C21 C24 C25 O5 -136.7(4) . . . . ? C23 C24 C25 O5 101.3(4) . . . . ? C21A C24 C25 O5 -72.1(8) . . . . ? C22 C24 C25 O5 -16.6(5) . . . . ? C23A C24 C25 O5 169.3(8) . . . . ? C22A C24 C25 C26 -127.5(10) . . . . ? C21 C24 C25 C26 44.6(5) . . . . ? C23 C24 C25 C26 -77.4(4) . . . . ? C21A C24 C25 C26 109.1(8) . . . . ? C22 C24 C25 C26 164.7(4) . . . . ? C23A C24 C25 C26 -9.5(9) . . . . ? O5 C25 C26 C27 5.8(5) . . . . ? C24 C25 C26 C27 -175.5(3) . . . . ? C25 C26 C27 O6 -4.9(5) . . . . ? C25 C26 C27 C28 174.7(3) . . . . ? O6 C27 C28 C33 161.2(3) . . . . ? C26 C27 C28 C33 -18.4(5) . . . . ? O6 C27 C28 C29 -15.7(4) . . . . ? C26 C27 C28 C29 164.8(3) . . . . ? C33 C28 C29 C30 -0.3(4) . . . . ? C27 C28 C29 C30 176.8(3) . . . . ? C28 C29 C30 C31 -0.5(4) . . . . ? C28 C29 C30 C34 179.7(3) . . . . ? C29 C30 C31 C32 0.9(5) . . . . ? C34 C30 C31 C32 -179.4(3) . . . . ? C30 C31 C32 C33 -0.3(5) . . . . ? C31 C32 C33 C28 -0.5(5) . . . . ? C29 C28 C33 C32 0.8(5) . . . . ? C27 C28 C33 C32 -176.0(3) . . . . ? C29 C30 C34 O7 16.6(4) . . . . ? C31 C30 C34 O7 -163.1(3) . . . . ? C29 C30 C34 C35 -163.5(3) . . . . ? C31 C30 C34 C35 16.8(4) . . . . ? O7 C34 C35 C36 -0.1(5) . . . . ? C30 C34 C35 C36 -180.0(3) . . . . ? C34 C35 C36 O8 -4.0(5) . . . . ? C34 C35 C36 C37 176.3(3) . . . . ? O8 C36 C37 C39 46.8(4) . . . . ? C35 C36 C37 C39 -133.5(3) . . . . ? O8 C36 C37 C40 168.0(3) . . . . ? C35 C36 C37 C40 -12.2(4) . . . . ? O8 C36 C37 C38 -70.9(4) . . . . ? C35 C36 C37 C38 108.8(3) . . . . ? N1 C41 C42 C43 -54.7(5) . . . . ? C41 C42 C43 C44 52.7(5) . . . . ? C42 C43 C44 C45 -53.4(5) . . . . ? C43 C44 C45 N1 55.8(5) . . . . ? N2 C46 C47 C48 -46.2(6) . . . . ? C46 C47 C48 C49 43.8(6) . . . . ? C47 C48 C49 C50 -42.0(6) . . . . ? C48 C49 C50 N2 42.3(6) . . . . ? N3 C51 C52 C53 52.8(5) . . . . ? C51 C52 C53 C54 -50.8(5) . . . . ? C52 C53 C54 C55 51.5(5) . . . . ? C53 C54 C55 N3 -53.8(4) . . . . ? N4 C56 C57 C58 45.4(7) . . . . ? C56 C57 C58 C59 -45.0(8) . . . . ? C57 C58 C59 C60 45.5(7) . . . . ? C58 C59 C60 N4 -47.6(6) . . . . ? N5 C61 C62 C63 53.3(7) . . . . ? C63 C64 C65 N5 -55.9(9) . . . . ? C65 C64 C63 C62 50.0(9) . . . . ? C61 C62 C63 C64 -47.7(8) . . . . ? N5A C61A C62A C63A 68(2) . . . . ? C61A C62A C63A C65A -74(2) . . . . ? C62A C63A C65A C64A 76(2) . . . . ? C63A C65A C64A N5A -77(3) . . . . ? C42 C41 N1 C45 54.8(4) . . . . ? C42 C41 N1 Ni1 -172.2(3) . . . . ? C44 C45 N1 C41 -55.3(4) . . . . ? C44 C45 N1 Ni1 171.0(3) . . . . ? C49 C50 N2 C46 -43.2(5) . . . . ? C49 C50 N2 Ni1 170.6(3) . . . . ? C47 C46 N2 C50 45.2(5) . . . . ? C47 C46 N2 Ni1 -167.7(3) . . . . ? C54 C55 N3 C51 54.3(4) . . . . ? C54 C55 N3 Ni2 -172.5(2) . . . . ? C52 C51 N3 C55 -53.8(4) . . . . ? C52 C51 N3 Ni2 173.3(3) . . . . ? C59 C60 N4 C56 48.0(5) . . . . ? C59 C60 N4 Ni2 -168.1(3) . . . . ? C57 C56 N4 C60 -46.2(6) . . . . ? C57 C56 N4 Ni2 169.7(4) . . . . ? C64 C65 N5 C61 63.8(7) . . . . ? C62 C61 N5 C65 -63.8(7) . . . . ? C65A C64A N5A C61A 58.2(19) . . . . ? C62A C61A N5A C64A -59.5(18) . . . . ? C6 C5 O1 Ni1 -4.7(4) . . . . ? C4 C5 O1 Ni1 175.1(2) . . . . ? C6 C7 O2 Ni1 12.6(4) . . . . ? C8 C7 O2 Ni1 -165.83(18) . . . . ? C15 C14 O3 Ni2 -16.6(4) . . . . ? C10 C14 O3 Ni2 162.10(19) . . . . ? C15 C16 O4 Ni2 7.3(5) . . . . ? C17 C16 O4 Ni2 -170.57(19) . . . . ? C26 C25 O5 Ni1 7.7(5) . . . . ? C24 C25 O5 Ni1 -171.0(2) . . . . ? C26 C27 O6 Ni1 -9.3(4) . . . . ? C28 C27 O6 Ni1 171.12(18) . . . . ? C35 C34 O7 Ni2 9.2(4) . . . . ? C30 C34 O7 Ni2 -170.88(18) . . . . ? C35 C36 O8 Ni2 -1.8(5) . . . . ? C37 C36 O8 Ni2 177.86(19) . . . . ? C5 O1 Ni1 O5 -166.0(3) . . . . ? C5 O1 Ni1 O2 11.4(3) . . . . ? C5 O1 Ni1 N1 101.1(3) . . . . ? C5 O1 Ni1 N2 -80.2(3) . . . . ? C25 O5 Ni1 O1 162.9(3) . . . . ? C25 O5 Ni1 O6 -15.1(3) . . . . ? C25 O5 Ni1 N1 -103.5(3) . . . . ? C25 O5 Ni1 N2 70.8(3) . . . . ? C7 O2 Ni1 O1 -15.2(2) . . . . ? C7 O2 Ni1 O6 162.8(2) . . . . ? C7 O2 Ni1 N1 -108.8(2) . . . . ? C7 O2 Ni1 N2 76.9(2) . . . . ? C27 O6 Ni1 O5 15.7(2) . . . . ? C27 O6 Ni1 O2 -161.7(2) . . . . ? C27 O6 Ni1 N1 108.7(2) . . . . ? C27 O6 Ni1 N2 -70.2(2) . . . . ? C41 N1 Ni1 O1 -17.4(3) . . . . ? C45 N1 Ni1 O1 113.3(2) . . . . ? C41 N1 Ni1 O5 -107.0(2) . . . . ? C45 N1 Ni1 O5 23.7(2) . . . . ? C41 N1 Ni1 O2 72.4(2) . . . . ? C45 N1 Ni1 O2 -156.9(2) . . . . ? C41 N1 Ni1 O6 163.5(2) . . . . ? C45 N1 Ni1 O6 -65.7(2) . . . . ? C50 N2 Ni1 O1 116.1(3) . . . . ? C46 N2 Ni1 O1 -29.0(3) . . . . ? C50 N2 Ni1 O5 -154.6(3) . . . . ? C46 N2 Ni1 O5 60.3(3) . . . . ? C50 N2 Ni1 O2 26.2(3) . . . . ? C46 N2 Ni1 O2 -118.9(3) . . . . ? C50 N2 Ni1 O6 -64.9(3) . . . . ? C46 N2 Ni1 O6 150.1(3) . . . . ? C16 O4 Ni2 O8 161.4(3) . . . . ? C16 O4 Ni2 O3 -15.5(3) . . . . ? C16 O4 Ni2 N3 -104.6(3) . . . . ? C16 O4 Ni2 N4 69.7(3) . . . . ? C34 O7 Ni2 O8 -10.8(2) . . . . ? C34 O7 Ni2 O3 166.1(2) . . . . ? C34 O7 Ni2 N3 -104.7(2) . . . . ? C34 O7 Ni2 N4 80.9(2) . . . . ? C36 O8 Ni2 O4 -173.1(3) . . . . ? C36 O8 Ni2 O7 7.3(3) . . . . ? C36 O8 Ni2 N3 95.7(3) . . . . ? C36 O8 Ni2 N4 -85.2(3) . . . . ? C14 O3 Ni2 O4 19.9(2) . . . . ? C14 O3 Ni2 O7 -160.5(2) . . . . ? C14 O3 Ni2 N3 111.0(2) . . . . ? C14 O3 Ni2 N4 -68.2(2) . . . . ? C55 N3 Ni2 O4 -98.1(2) . . . . ? C51 N3 Ni2 O4 32.9(2) . . . . ? C55 N3 Ni2 O7 81.1(2) . . . . ? C51 N3 Ni2 O7 -147.9(2) . . . . ? C55 N3 Ni2 O8 -8.5(2) . . . . ? C51 N3 Ni2 O8 122.5(2) . . . . ? C55 N3 Ni2 O3 172.8(2) . . . . ? C51 N3 Ni2 O3 -56.2(2) . . . . ? C60 N4 Ni2 O4 66.0(3) . . . . ? C56 N4 Ni2 O4 -151.5(3) . . . . ? C60 N4 Ni2 O7 -113.2(3) . . . . ? C56 N4 Ni2 O7 29.3(3) . . . . ? C60 N4 Ni2 O8 -23.5(3) . . . . ? C56 N4 Ni2 O8 119.0(3) . . . . ? C60 N4 Ni2 O3 155.3(3) . . . . ? C56 N4 Ni2 O3 -62.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N N5 0.891(10) 2.188(13) 3.070(6) 170(3) . N3 H3N N5A 0.886(10) 2.19(2) 3.047(14) 162(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.662 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.064 # Attachment 'Fig_5.CIF' data_lj252sad _database_code_depnum_ccdc_archive 'CCDC 754708' #TrackingRef 'Fig_5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C50 H70 Cu2 N2 O8, C10 H22 N2' _chemical_formula_sum 'C60 H92 Cu2 N4 O8' _chemical_formula_weight 1124.46 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/m _symmetry_space_group_name_Hall '-C 2y' #_symmetry_international_tables_no '12' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 9.9434(4) _cell_length_b 19.2818(7) _cell_length_c 15.7332(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.706(2) _cell_angle_gamma 90.00 _cell_volume 2989.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4938 _cell_measurement_theta_min 2.616 _cell_measurement_theta_max 27.78 _exptl_crystal_description blade _exptl_crystal_colour green _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.070 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 0.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17063 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3789 _reflns_number_gt 3048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0489P)^2^+16.1580P] 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 3789 _refine_ls_number_parameters 177 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6544(4) 0.1755(2) 0.0792(2) 0.0443(10) Uani 1 1 d . . . H1A H 0.5724 0.1992 0.0923 0.066 Uiso 1 1 calc R . . H1B H 0.6324 0.1274 0.0628 0.066 Uiso 1 1 calc R . . H1C H 0.6895 0.1994 0.0317 0.066 Uiso 1 1 calc R . . C2 C 0.8897(4) 0.1408(2) 0.1370(3) 0.0396(9) Uani 1 1 d . . . H2A H 0.8690 0.0922 0.1222 0.059 Uiso 1 1 calc R . . H2B H 0.9608 0.1428 0.1865 0.059 Uiso 1 1 calc R . . H2C H 0.9214 0.1642 0.0881 0.059 Uiso 1 1 calc R . . C3 C 0.7941(5) 0.2515(2) 0.1838(3) 0.0468(11) Uani 1 1 d . . . H3A H 0.8316 0.2751 0.1371 0.070 Uiso 1 1 calc R . . H3B H 0.8603 0.2529 0.2359 0.070 Uiso 1 1 calc R . . H3C H 0.7105 0.2749 0.1946 0.070 Uiso 1 1 calc R . . C4 C 0.7627(3) 0.17651(17) 0.1589(2) 0.0268(7) Uani 1 1 d . . . C5 C 0.7044(3) 0.13403(16) 0.22879(19) 0.0217(6) Uani 1 1 d . . . C6 C 0.6622(4) 0.16729(17) 0.2998(2) 0.0304(8) Uani 1 1 d . A . H6 H 0.6781 0.2157 0.3060 0.036 Uiso 1 1 calc R . . C7 C 0.5981(4) 0.13369(16) 0.3623(2) 0.0279(7) Uani 1 1 d . . . C9 C 0.5000 0.1402(2) 0.5000 0.0349(10) Uani 1 2 d SD . . H9 H 0.5000 0.0921 0.5000 0.042 Uiso 1 calc d SD A . C8 C 0.585(3) 0.1734(13) 0.4443(15) 0.0349(10) Uani 0.25 1 d P A 1 C10 C 0.5852(17) 0.2789(7) 0.5269(9) 0.0349(10) Uani 0.25 1 d P . 1 H10 H 0.6049 0.3270 0.5334 0.042 Uiso 0.25 1 calc PR . 1 C11 C 0.620(2) 0.2436(7) 0.4567(9) 0.0349(10) Uani 0.25 1 d P A 1 H11 H 0.6671 0.2669 0.4166 0.042 Uiso 0.25 1 calc PR A 1 C11A C 0.477(2) 0.2450(7) 0.4127(10) 0.0349(10) Uani 0.25 1 d P . 1 H11A H 0.4896 0.2682 0.3611 0.042 Uiso 0.25 1 calc PR . 1 C8A C 0.525(4) 0.175(2) 0.426(3) 0.0349(10) Uani 0.25 1 d P A 1 C10A C 0.5000 0.2841(5) 0.5000 0.0349(10) Uani 0.50 2 d SP . 3 H10A H 0.5000 0.3333 0.5000 0.042 Uiso 0.50 2 calc SPR . 3 C11B C 0.5449(11) 0.2480(4) 0.4330(5) 0.0349(10) Uani 0.50 1 d P A 3 H11B H 0.5749 0.2728 0.3869 0.042 Uiso 0.50 1 calc PR A 3 C8B C 0.5467(19) 0.1750(13) 0.4324(15) 0.0349(10) Uani 0.50 1 d P A 3 C12 C 0.3738(4) -0.06293(18) 0.1549(2) 0.0329(8) Uani 1 1 d . . . H12A H 0.3876 -0.1041 0.1927 0.039 Uiso 1 1 calc R . . H12B H 0.4388 -0.0661 0.1125 0.039 Uiso 1 1 calc R . . C13 C 0.2304(4) -0.0644(2) 0.1076(3) 0.0417(9) Uani 1 1 d . . . H13A H 0.2182 -0.1063 0.0709 0.050 Uiso 1 1 calc R . . H13B H 0.1647 -0.0668 0.1495 0.050 Uiso 1 1 calc R . . C14 C 0.2034(6) 0.0000 0.0525(4) 0.0442(14) Uani 1 2 d S . . H14A H 0.2630 0.0000 0.0068 0.053 Uiso 1 2 calc SR . . H14B H 0.1080 0.0000 0.0247 0.053 Uiso 1 2 calc SR . . C15 C 0.2221(12) 0.0554(8) 0.3914(10) 0.0815(16) Uani 0.50 1 d P . 1 H15A H 0.2731 0.0836 0.3540 0.098 Uiso 0.50 1 calc PR . 1 H15B H 0.2372 0.0770 0.4489 0.098 Uiso 0.50 1 calc PR . 1 C16 C 0.0776(12) 0.0644(6) 0.3592(11) 0.0815(16) Uani 0.50 1 d PD . 1 H16A H 0.0690 0.0774 0.2979 0.098 Uiso 0.50 1 calc PR . 1 H16B H 0.0419 0.1034 0.3905 0.098 Uiso 0.50 1 calc PR . 1 C17 C -0.0110(15) 0.0000 0.3683(15) 0.0815(16) Uani 0.50 2 d SPD . 1 H17A H -0.0906 0.0000 0.3232 0.098 Uiso 0.50 2 calc SPR . 1 H17B H -0.0439 0.0000 0.4250 0.098 Uiso 0.50 2 calc SPR . 1 N2 N 0.2759(19) 0.0000 0.3981(12) 0.0815(16) Uani 0.50 2 d SP . 1 C16A C 0.0213(11) 0.0535(8) 0.3649(11) 0.0815(16) Uani 0.50 1 d P . 2 H16C H -0.0138 0.0441 0.4198 0.098 Uiso 0.50 1 calc PR . 2 H16D H -0.0297 0.0933 0.3370 0.098 Uiso 0.50 1 calc PR . 2 N2A N 0.2599(19) 0.0000 0.3664(12) 0.0815(16) Uani 0.50 2 d SP . 2 C17A C 0.0027(18) 0.0000 0.3162(14) 0.0815(16) Uani 0.50 2 d SP . 2 H17C H 0.0679 0.0000 0.2738 0.098 Uiso 0.50 2 calc SPR . 2 H17D H -0.0906 0.0000 0.2849 0.098 Uiso 0.50 2 calc SPR . 2 C15A C 0.1637(13) 0.0707(8) 0.3818(10) 0.0815(16) Uani 0.50 1 d P . 2 H15C H 0.1859 0.0872 0.4416 0.098 Uiso 0.50 1 calc PR . 2 H15D H 0.1844 0.1085 0.3430 0.098 Uiso 0.50 1 calc PR . 2 N1 N 0.4037(4) 0.0000 0.2069(2) 0.0236(8) Uani 1 2 d SD . . H1N H 0.351(5) 0.0000 0.248(3) 0.035 Uiso 1 2 d SD . . O1 O 0.6930(2) 0.06987(11) 0.21325(14) 0.0234(5) Uani 1 1 d . A . O2 O 0.5745(3) 0.06901(11) 0.36457(14) 0.0277(5) Uani 1 1 d . A . Cu1 Cu 0.61450(6) 0.0000 0.28119(3) 0.01795(16) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.047(2) 0.054(3) 0.033(2) 0.0190(18) 0.0112(17) -0.004(2) C2 0.039(2) 0.039(2) 0.046(2) 0.0058(17) 0.0230(18) -0.0007(17) C3 0.072(3) 0.027(2) 0.049(2) -0.0018(17) 0.034(2) -0.015(2) C4 0.0324(18) 0.0203(16) 0.0307(16) 0.0035(13) 0.0156(14) -0.0047(13) C5 0.0230(15) 0.0197(15) 0.0227(15) 0.0026(12) 0.0048(12) -0.0029(12) C6 0.053(2) 0.0143(15) 0.0267(16) -0.0016(12) 0.0144(15) -0.0082(15) C7 0.049(2) 0.0160(15) 0.0205(15) -0.0007(12) 0.0101(14) -0.0012(14) C9 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C8 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C10 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C11 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C11A 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C8A 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C10A 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C11B 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C8B 0.070(3) 0.0145(11) 0.0246(18) 0.000 0.0203(19) 0.000 C12 0.039(2) 0.0225(17) 0.0364(19) -0.0046(14) 0.0010(15) -0.0035(15) C13 0.040(2) 0.041(2) 0.042(2) -0.0058(18) -0.0009(17) -0.0124(18) C14 0.039(3) 0.049(4) 0.040(3) 0.000 -0.007(2) 0.000 C15 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) C16 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) C17 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) N2 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) C16A 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) N2A 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) C17A 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) C15A 0.042(3) 0.088(4) 0.108(4) -0.021(3) -0.013(4) 0.011(4) N1 0.029(2) 0.0172(18) 0.026(2) 0.000 0.0077(16) 0.000 O1 0.0320(12) 0.0162(11) 0.0240(11) 0.0003(8) 0.0114(9) -0.0018(9) O2 0.0485(15) 0.0140(11) 0.0233(11) -0.0011(9) 0.0152(10) -0.0034(10) Cu1 0.0260(3) 0.0119(3) 0.0174(3) 0.000 0.00835(19) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.541(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.519(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.520(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.545(4) . ? C5 O1 1.263(4) . ? C5 C6 1.400(4) . ? C6 C7 1.400(4) . ? C6 H6 0.9500 . ? C7 O2 1.271(4) . ? C7 C8B 1.50(3) . ? C7 C8 1.52(3) . ? C7 C8A 1.54(4) . ? C9 C8B 1.39(3) 2_656 ? C9 C8B 1.39(3) . ? C9 C8A 1.39(4) . ? C9 C8 1.45(3) . ? C9 C8 1.45(3) 2_656 ? C9 H9 0.9300 . ? C8 C11 1.40(3) . ? C10 C11A 1.370(19) 2_656 ? C10 C11 1.379(18) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C11A C10 1.370(19) 2_656 ? C11A C8A 1.43(4) . ? C11A H11A 0.9500 . ? C10A C11B 1.386(9) . ? C10A C11B 1.386(9) 2_656 ? C10A H10A 0.9500 . ? C11B C8B 1.41(3) . ? C11B H11B 0.9500 . ? C12 N1 1.472(4) . ? C12 C13 1.518(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.518(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C13 1.518(5) 6 ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N2 1.192(17) . ? C15 C16 1.468(16) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5408(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C16 1.5408(10) 6 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N2 C15 1.192(17) 6 ? C16A C17A 1.284(18) . ? C16A C15A 1.444(16) . ? C16A H16C 0.9900 . ? C16A H16D 0.9900 . ? N2A C15A 1.701(19) 6 ? N2A C15A 1.701(19) . ? C17A C16A 1.284(18) 6 ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? N1 C12 1.472(4) 6 ? N1 Cu1 2.259(4) . ? N1 H1N 0.89(5) . ? O1 Cu1 1.947(2) . ? O2 Cu1 1.947(2) . ? Cu1 O1 1.947(2) 6 ? Cu1 O2 1.947(2) 6 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 C3 110.0(3) . . ? C2 C4 C1 108.7(3) . . ? C3 C4 C1 108.6(3) . . ? C2 C4 C5 108.9(3) . . ? C3 C4 C5 113.9(3) . . ? C1 C4 C5 106.5(3) . . ? O1 C5 C6 125.0(3) . . ? O1 C5 C4 114.5(3) . . ? C6 C5 C4 120.4(3) . . ? C7 C6 C5 124.2(3) . . ? C7 C6 H6 117.9 . . ? C5 C6 H6 117.9 . . ? O2 C7 C6 125.3(3) . . ? O2 C7 C8B 114.6(10) . . ? C6 C7 C8B 120.1(10) . . ? O2 C7 C8 115.7(10) . . ? C6 C7 C8 117.4(10) . . ? O2 C7 C8A 112.6(15) . . ? C6 C7 C8A 121.2(15) . . ? C8B C9 C8B 122(2) 2_656 . ? C8B C9 C8A 121.5(9) 2_656 . ? C8B C9 C8 122.3(8) 2_656 . ? C8B C9 C8 122.3(8) . 2_656 ? C8A C9 C8 118(2) . 2_656 ? C8 C9 C8 128(2) . 2_656 ? C8B C9 H9 118.8(11) 2_656 . ? C8B C9 H9 118.8(11) . . ? C8A C9 H9 118.8(17) . . ? C8 C9 H9 116.2(10) . . ? C8 C9 H9 116.2(10) 2_656 . ? C11 C8 C9 119.6(19) . . ? C11 C8 C7 123.9(18) . . ? C9 C8 C7 114.4(16) . . ? C11 C8 C11A 54.3(12) . . ? C9 C8 C11A 97.5(15) . . ? C7 C8 C11A 105.6(14) . . ? C11A C10 C11 120.3(13) 2_656 . ? C11A C10 H10 119.9 2_656 . ? C11 C10 H10 119.9 . . ? C10 C11 C8 120.4(16) . . ? C10 C11 H11 119.8 . . ? C8 C11 H11 119.8 . . ? C10 C11A C8A 121(2) 2_656 . ? C10 C11A C8 119.4(15) 2_656 . ? C10 C11A H11A 119.4 2_656 . ? C8A C11A H11A 119.4 . . ? C8 C11A H11A 117.6 . . ? C9 C8A C11A 119(3) . . ? C9 C8A C7 117(3) . . ? C11A C8A C7 124(3) . . ? C11B C10A C11B 119.7(9) . 2_656 ? C11B C10A H10A 120.2 . . ? C11B C10A H10A 120.2 2_656 . ? C10A C11B C8B 120.9(12) . . ? C10A C11B H11B 119.6 . . ? C8B C11B H11B 119.6 . . ? C9 C8B C11B 118.1(18) . . ? C9 C8B C7 119.2(17) . . ? C11B C8B C7 122.7(18) . . ? N1 C12 C13 113.2(3) . . ? N1 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N1 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 110.3(4) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C13 109.8(5) 6 . ? C13 C14 H14A 109.7 6 . ? C13 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 6 . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N2 C15 C16 122.9(13) . . ? N2 C15 H15A 106.6 . . ? C16 C15 H15A 106.6 . . ? N2 C15 H15B 106.6 . . ? C16 C15 H15B 106.6 . . ? H15A C15 H15B 106.6 . . ? C15 C16 C17 114.7(12) . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C16 107.4(14) . 6 ? C16 C17 H17A 110.2 . . ? C16 C17 H17A 110.2 6 . ? C16 C17 H17B 110.2 . . ? C16 C17 H17B 110.2 6 . ? H17A C17 H17B 108.5 . . ? C15 N2 C15 127.1(19) . 6 ? C17A C16A C15A 110.7(14) . . ? C17A C16A H16C 109.5 . . ? C15A C16A H16C 109.5 . . ? C17A C16A H16D 109.5 . . ? C15A C16A H16D 109.5 . . ? H16C C16A H16D 108.1 . . ? C15A N2A C15A 106.5(15) 6 . ? C16A C17A C16A 107(2) . 6 ? C16A C17A H17C 110.3 . . ? C16A C17A H17C 110.3 6 . ? C16A C17A H17D 110.3 . . ? C16A C17A H17D 110.3 6 . ? H17C C17A H17D 108.6 . . ? C16A C15A N2A 110.3(11) . . ? C16A C15A H15C 109.6 . . ? N2A C15A H15C 109.6 . . ? C16A C15A H15D 109.6 . . ? N2A C15A H15D 109.6 . . ? H15C C15A H15D 108.1 . . ? C12 N1 C12 111.1(4) 6 . ? C12 N1 Cu1 113.1(2) 6 . ? C12 N1 Cu1 113.1(2) . . ? C12 N1 H1N 108.3(19) 6 . ? C12 N1 H1N 108.3(19) . . ? Cu1 N1 H1N 102(4) . . ? C5 O1 Cu1 127.13(19) . . ? C7 O2 Cu1 126.6(2) . . ? O1 Cu1 O1 87.58(13) . 6 ? O1 Cu1 O2 91.73(9) . . ? O1 Cu1 O2 167.47(10) 6 . ? O1 Cu1 O2 167.47(10) . 6 ? O1 Cu1 O2 91.73(9) 6 6 ? O2 Cu1 O2 86.23(13) . 6 ? O1 Cu1 N1 97.38(10) . . ? O1 Cu1 N1 97.38(10) 6 . ? O2 Cu1 N1 95.11(10) . . ? O2 Cu1 N1 95.11(10) 6 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C4 C5 O1 -48.8(4) . . . . ? C3 C4 C5 O1 -172.0(3) . . . . ? C1 C4 C5 O1 68.3(4) . . . . ? C2 C4 C5 C6 134.6(4) . . . . ? C3 C4 C5 C6 11.3(5) . . . . ? C1 C4 C5 C6 -108.3(4) . . . . ? O1 C5 C6 C7 -1.7(6) . . . . ? C4 C5 C6 C7 174.5(3) . . . . ? C5 C6 C7 O2 2.7(6) . . . . ? C5 C6 C7 C8B -175.2(8) . . . . ? C5 C6 C7 C8 167.5(10) . . . . ? C5 C6 C7 C8A -165.4(15) . . . . ? C8B C9 C8 C11 -2(3) 2_656 . . . ? C8B C9 C8 C11 94(7) . . . . ? C8A C9 C8 C11 95(4) . . . . ? C8 C9 C8 C11 16.9(15) 2_656 . . . ? C8B C9 C8 C7 -166.0(11) 2_656 . . . ? C8B C9 C8 C7 -71(6) . . . . ? C8A C9 C8 C7 -70(3) . . . . ? C8 C9 C8 C7 -147.2(18) 2_656 . . . ? C8B C9 C8 C11A -55(2) 2_656 . . . ? C8B C9 C8 C11A 40(6) . . . . ? C8A C9 C8 C11A 41(3) . . . . ? C8 C9 C8 C11A -36.1(8) 2_656 . . . ? O2 C7 C8 C11 173.8(17) . . . . ? C6 C7 C8 C11 7(2) . . . . ? C8B C7 C8 C11 -97(7) . . . . ? C8A C7 C8 C11 -98(4) . . . . ? O2 C7 C8 C9 -22.9(18) . . . . ? C6 C7 C8 C9 170.8(10) . . . . ? C8B C7 C8 C9 67(6) . . . . ? C8A C7 C8 C9 65(3) . . . . ? O2 C7 C8 C11A -129.0(11) . . . . ? C6 C7 C8 C11A 64.7(16) . . . . ? C8B C7 C8 C11A -39(6) . . . . ? C8A C7 C8 C11A -41(3) . . . . ? C11A C10 C11 C8 3(3) 2_656 . . . ? C9 C8 C11 C10 7(3) . . . . ? C7 C8 C11 C10 169.5(17) . . . . ? C11A C8 C11 C10 84.2(19) . . . . ? C11 C8 C11A C10 -78.1(18) . . . 2_656 ? C9 C8 C11A C10 43(2) . . . 2_656 ? C7 C8 C11A C10 161.2(15) . . . 2_656 ? C11 C8 C11A C8A -179(5) . . . . ? C9 C8 C11A C8A -58(5) . . . . ? C7 C8 C11A C8A 60(5) . . . . ? C8B C9 C8A C11A -12(4) 2_656 . . . ? C8B C9 C8A C11A -110(17) . . . . ? C8 C9 C8A C11A -112(4) . . . . ? C8 C9 C8A C11A 7(3) 2_656 . . . ? C8B C9 C8A C7 170.2(11) 2_656 . . . ? C8B C9 C8A C7 72(16) . . . . ? C8 C9 C8A C7 70(3) . . . . ? C8 C9 C8A C7 -171(2) 2_656 . . . ? C10 C11A C8A C9 3(4) 2_656 . . . ? C8 C11A C8A C9 93(5) . . . . ? C10 C11A C8A C7 -179(2) 2_656 . . . ? C8 C11A C8A C7 -89(5) . . . . ? O2 C7 C8A C9 29(3) . . . . ? C6 C7 C8A C9 -161.5(16) . . . . ? C8B C7 C8A C9 -76(16) . . . . ? C8 C7 C8A C9 -74(3) . . . . ? O2 C7 C8A C11A -149(2) . . . . ? C6 C7 C8A C11A 21(3) . . . . ? C8B C7 C8A C11A 106(17) . . . . ? C8 C7 C8A C11A 108(4) . . . . ? C11B C10A C11B C8B -0.6(9) 2_656 . . . ? C8B C9 C8B C11B -0.5(9) 2_656 . . . ? C8A C9 C8B C11B 87(16) . . . . ? C8 C9 C8B C11B -96(7) . . . . ? C8 C9 C8B C11B 19(2) 2_656 . . . ? C8B C9 C8B C7 178.9(15) 2_656 . . . ? C8A C9 C8B C7 -93(16) . . . . ? C8 C9 C8B C7 84(7) . . . . ? C8 C9 C8B C7 -161.8(10) 2_656 . . . ? C10A C11B C8B C9 1.1(18) . . . . ? C10A C11B C8B C7 -178.3(9) . . . . ? O2 C7 C8B C9 10.5(14) . . . . ? C6 C7 C8B C9 -171.5(8) . . . . ? C8 C7 C8B C9 -87(7) . . . . ? C8A C7 C8B C9 89(16) . . . . ? O2 C7 C8B C11B -170.1(11) . . . . ? C6 C7 C8B C11B 7.9(17) . . . . ? C8 C7 C8B C11B 92(7) . . . . ? C8A C7 C8B C11B -92(16) . . . . ? N1 C12 C13 C14 55.6(5) . . . . ? C12 C13 C14 C13 -55.8(6) . . . 6 ? N2 C15 C16 C17 23(2) . . . . ? C15 C16 C17 C16 -32(2) . . . 6 ? C16 C15 N2 C15 -10(4) . . . 6 ? C15A C16A C17A C16A 84(2) . . . 6 ? C17A C16A C15A N2A -22(2) . . . . ? C15A N2A C15A C16A -25(2) 6 . . . ? C13 C12 N1 C12 -53.9(5) . . . 6 ? C13 C12 N1 Cu1 177.7(2) . . . . ? C6 C5 O1 Cu1 0.4(5) . . . . ? C4 C5 O1 Cu1 -176.1(2) . . . . ? C6 C7 O2 Cu1 -2.2(6) . . . . ? C8B C7 O2 Cu1 175.8(7) . . . . ? C8 C7 O2 Cu1 -167.3(10) . . . . ? C8A C7 O2 Cu1 166.8(14) . . . . ? C5 O1 Cu1 O1 -167.4(2) . . . 6 ? C5 O1 Cu1 O2 0.1(3) . . . . ? C5 O1 Cu1 O2 -80.3(5) . . . 6 ? C5 O1 Cu1 N1 95.5(3) . . . . ? C7 O2 Cu1 O1 0.8(3) . . . . ? C7 O2 Cu1 O1 87.4(5) . . . 6 ? C7 O2 Cu1 O2 168.4(3) . . . 6 ? C7 O2 Cu1 N1 -96.8(3) . . . . ? C12 N1 Cu1 O1 -19.4(3) 6 . . . ? C12 N1 Cu1 O1 107.9(2) . . . . ? C12 N1 Cu1 O1 -107.9(2) 6 . . 6 ? C12 N1 Cu1 O1 19.4(3) . . . 6 ? C12 N1 Cu1 O2 73.0(3) 6 . . . ? C12 N1 Cu1 O2 -159.7(2) . . . . ? C12 N1 Cu1 O2 159.7(2) 6 . . 6 ? C12 N1 Cu1 O2 -73.0(3) . . . 6 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N N2A 0.89(5) 2.17(3) 3.05(2) 169(5) . N1 H1N N2 0.89(5) 2.56(3) 3.42(2) 161(5) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.511 _refine_diff_density_min -1.266 _refine_diff_density_rms 0.097 # Attachment 'Fig_6_Co.CIF' data_lj170sad _database_code_depnum_ccdc_archive 'CCDC 754709' #TrackingRef 'Fig_6_Co.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C52 H80 Co2 N4 O8 ' _chemical_formula_sum ' C52 H80 Co2 N4 O8 ' _chemical_formula_weight 1007.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' #_symmetry_international_tables_no '15' 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 29.6686(16) _cell_length_b 10.3395(7) _cell_length_c 19.7231(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.835(3) _cell_angle_gamma 90.00 _cell_volume 5490.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2893 _cell_measurement_theta_min 2.504 _cell_measurement_theta_max 25.283 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.290 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 0.656 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32042 _diffrn_reflns_av_R_equivalents 0.0941 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6799 _reflns_number_gt 3962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0539P)^2^+5.4719P] 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 6799 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.53715(14) 0.1864(5) -0.1160(2) 0.0682(13) Uani 1 1 d . . . H1A H 0.5251 0.1144 -0.0958 0.102 Uiso 1 1 calc R . . H1B H 0.5114 0.2119 -0.1647 0.102 Uiso 1 1 calc R . . H1C H 0.5452 0.2599 -0.0815 0.102 Uiso 1 1 calc R . . C2 C 0.57149(13) 0.0277(4) -0.17751(19) 0.0524(10) Uani 1 1 d . . . H2A H 0.6014 0.0009 -0.1833 0.079 Uiso 1 1 calc R . . H2B H 0.5455 0.0513 -0.2264 0.079 Uiso 1 1 calc R . . H2C H 0.5598 -0.0439 -0.1564 0.079 Uiso 1 1 calc R . . C3 C 0.60183(14) 0.2584(4) -0.15715(19) 0.0543(10) Uani 1 1 d . . . H3A H 0.6104 0.3312 -0.1222 0.081 Uiso 1 1 calc R . . H3B H 0.5754 0.2847 -0.2051 0.081 Uiso 1 1 calc R . . H3C H 0.6312 0.2319 -0.1645 0.081 Uiso 1 1 calc R . . C4 C 0.58362(12) 0.1442(4) -0.12512(17) 0.0411(8) Uani 1 1 d . . . C5 C 0.62425(11) 0.1038(3) -0.04891(16) 0.0317(7) Uani 1 1 d . . . C6 C 0.67178(11) 0.0737(3) -0.04355(16) 0.0309(7) Uani 1 1 d . . . H6 H 0.6776 0.0883 -0.0867 0.037 Uiso 1 1 calc R . . C7 C 0.71104(11) 0.0246(3) 0.01906(16) 0.0266(6) Uani 1 1 d . . . C8 C 0.75913(11) -0.0049(3) 0.01499(15) 0.0259(6) Uani 1 1 d . . . C9 C 0.77667(10) 0.0711(3) -0.02732(15) 0.0240(6) Uani 1 1 d . . . H9 H 0.7572 0.1422 -0.0547 0.029 Uiso 1 1 calc R . . C10 C 0.82166(10) 0.0459(3) -0.03056(15) 0.0246(6) Uani 1 1 d . . . C11 C 0.85018(12) -0.0572(3) 0.01041(17) 0.0345(7) Uani 1 1 d . . . H11 H 0.8813 -0.0755 0.0093 0.041 Uiso 1 1 calc R . . C12 C 0.83326(13) -0.1337(3) 0.0531(2) 0.0427(9) Uani 1 1 d . . . H12 H 0.8528 -0.2046 0.0806 0.051 Uiso 1 1 calc R . . C13 C 0.78842(12) -0.1075(3) 0.05565(18) 0.0370(8) Uani 1 1 d . . . H13 H 0.7775 -0.1597 0.0854 0.044 Uiso 1 1 calc R . . C14 C 0.83821(11) 0.1363(3) -0.07620(15) 0.0253(6) Uani 1 1 d . . . C15 C 0.88080(11) 0.1085(3) -0.08745(16) 0.0307(7) Uani 1 1 d . . . H15 H 0.8974 0.0290 -0.0684 0.037 Uiso 1 1 calc R . . C16 C 0.90068(11) 0.1902(3) -0.12514(16) 0.0302(7) Uani 1 1 d . A . C17 C 0.94415(14) 0.1436(4) -0.1428(2) 0.0473(9) Uani 1 1 d . . . C18 C 0.9225(3) 0.1520(9) -0.2330(4) 0.0576(9) Uiso 0.50 1 d P A 1 H18A H 0.9135 0.2417 -0.2490 0.086 Uiso 0.50 1 calc PR A 1 H18B H 0.8930 0.0970 -0.2555 0.086 Uiso 0.50 1 calc PR A 1 H18C H 0.9479 0.1224 -0.2490 0.086 Uiso 0.50 1 calc PR A 1 C19 C 0.9858(3) 0.2279(9) -0.1117(5) 0.0576(9) Uiso 0.50 1 d P A 1 H19A H 1.0145 0.1877 -0.1156 0.086 Uiso 0.50 1 calc PR A 1 H19B H 0.9935 0.2439 -0.0590 0.086 Uiso 0.50 1 calc PR A 1 H19C H 0.9781 0.3100 -0.1390 0.086 Uiso 0.50 1 calc PR A 1 C20 C 0.9629(3) 0.0092(9) -0.1168(5) 0.0576(9) Uiso 0.50 1 d P A 1 H20A H 0.9910 -0.0099 -0.1289 0.086 Uiso 0.50 1 calc PR A 1 H20B H 0.9362 -0.0533 -0.1419 0.086 Uiso 0.50 1 calc PR A 1 H20C H 0.9736 0.0033 -0.0626 0.086 Uiso 0.50 1 calc PR A 1 C18A C 0.9931(3) 0.2097(9) -0.0758(5) 0.0576(9) Uiso 0.50 1 d P A 2 H18D H 1.0229 0.1880 -0.0830 0.086 Uiso 0.50 1 calc PR A 2 H18E H 0.9965 0.1767 -0.0273 0.086 Uiso 0.50 1 calc PR A 2 H18F H 0.9890 0.3039 -0.0771 0.086 Uiso 0.50 1 calc PR A 2 C19A C 0.9414(3) 0.1979(9) -0.2120(5) 0.0576(9) Uiso 0.50 1 d P A 2 H19D H 0.9383 0.2922 -0.2109 0.086 Uiso 0.50 1 calc PR A 2 H19E H 0.9123 0.1626 -0.2540 0.086 Uiso 0.50 1 calc PR A 2 H19F H 0.9715 0.1758 -0.2182 0.086 Uiso 0.50 1 calc PR A 2 C20A C 0.9481(3) -0.0064(9) -0.1439(5) 0.0576(9) Uiso 0.50 1 d P A 2 H20D H 0.9713 -0.0309 -0.1653 0.086 Uiso 0.50 1 calc PR A 2 H20E H 0.9153 -0.0432 -0.1742 0.086 Uiso 0.50 1 calc PR A 2 H20F H 0.9602 -0.0397 -0.0927 0.086 Uiso 0.50 1 calc PR A 2 C21 C 0.57514(14) -0.0813(4) 0.1082(3) 0.0600(11) Uani 1 1 d . . . H21A H 0.5589 -0.0630 0.0546 0.090 Uiso 1 1 calc R . . H21B H 0.5678 -0.0115 0.1357 0.090 Uiso 1 1 calc R . . H21C H 0.5627 -0.1634 0.1185 0.090 Uiso 1 1 calc R . . C22 C 0.63857(15) -0.1968(3) 0.0905(2) 0.0513(10) Uani 1 1 d . . . H22A H 0.6252 -0.2774 0.1007 0.077 Uiso 1 1 calc R . . H22B H 0.6745 -0.2057 0.1064 0.077 Uiso 1 1 calc R . . H22C H 0.6225 -0.1782 0.0369 0.077 Uiso 1 1 calc R . . C23 C 0.65352(15) -0.1145(3) 0.2136(2) 0.0505(10) Uani 1 1 d . . . H23A H 0.6495 -0.2067 0.2234 0.061 Uiso 1 1 calc R . . H23B H 0.6374 -0.0617 0.2390 0.061 Uiso 1 1 calc R . . C24 C 0.70752(14) -0.0823(3) 0.24486(19) 0.0480(9) Uani 1 1 d . . . H24A H 0.7229 -0.1003 0.2992 0.058 Uiso 1 1 calc R . . H24B H 0.7240 -0.1375 0.2210 0.058 Uiso 1 1 calc R . . C25 C 0.70683(14) 0.1405(4) 0.28518(18) 0.0465(9) Uani 1 1 d . . . H25A H 0.6734 0.1262 0.2823 0.070 Uiso 1 1 calc R . . H25B H 0.7101 0.2309 0.2729 0.070 Uiso 1 1 calc R . . H25C H 0.7315 0.1217 0.3359 0.070 Uiso 1 1 calc R . . C26 C 0.76709(12) 0.0718(4) 0.24160(19) 0.0452(9) Uani 1 1 d . . . H26A H 0.7720 0.1610 0.2292 0.068 Uiso 1 1 calc R . . H26B H 0.7738 0.0120 0.2084 0.068 Uiso 1 1 calc R . . H26C H 0.7898 0.0535 0.2936 0.068 Uiso 1 1 calc R . . N1 N 0.62881(10) -0.0900(2) 0.13195(15) 0.0352(6) Uani 1 1 d . . . N2 N 0.71501(10) 0.0550(2) 0.23196(14) 0.0351(6) Uani 1 1 d . . . O1 O 0.61185(7) 0.0965(2) 0.00520(11) 0.0335(5) Uani 1 1 d . . . O2 O 0.70969(7) -0.00025(19) 0.08224(10) 0.0291(5) Uani 1 1 d . . . O3 O 0.81034(7) 0.23369(19) -0.10340(11) 0.0294(5) Uani 1 1 d . . . O4 O 0.88566(7) 0.3040(2) -0.14660(11) 0.0320(5) Uani 1 1 d . . . Co1 Co 0.661344(15) 0.09100(4) 0.11563(2) 0.02622(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.043(2) 0.117(4) 0.038(2) 0.003(2) 0.0098(18) 0.029(2) C2 0.043(2) 0.073(3) 0.0333(19) -0.0102(19) 0.0086(17) -0.008(2) C3 0.060(2) 0.060(3) 0.033(2) 0.0048(18) 0.0093(18) 0.013(2) C4 0.0314(18) 0.063(2) 0.0271(17) -0.0045(16) 0.0104(15) 0.0058(17) C5 0.0319(17) 0.0409(18) 0.0245(15) -0.0053(14) 0.0140(13) -0.0044(14) C6 0.0307(17) 0.0433(19) 0.0216(15) 0.0005(14) 0.0138(13) -0.0004(14) C7 0.0331(17) 0.0263(15) 0.0258(15) -0.0004(12) 0.0177(14) -0.0047(13) C8 0.0309(17) 0.0257(14) 0.0248(15) -0.0013(12) 0.0153(13) -0.0009(12) C9 0.0258(15) 0.0244(15) 0.0198(14) -0.0017(11) 0.0077(12) -0.0006(12) C10 0.0282(16) 0.0226(13) 0.0238(15) -0.0024(12) 0.0119(13) -0.0034(12) C11 0.0369(18) 0.0357(17) 0.0376(18) 0.0040(14) 0.0222(15) 0.0057(14) C12 0.050(2) 0.0347(17) 0.054(2) 0.0197(16) 0.0316(18) 0.0167(16) C13 0.050(2) 0.0321(17) 0.0403(18) 0.0090(14) 0.0299(17) 0.0050(15) C14 0.0280(16) 0.0249(14) 0.0239(15) -0.0042(12) 0.0119(13) -0.0028(12) C15 0.0341(17) 0.0290(16) 0.0342(17) 0.0039(13) 0.0194(14) 0.0027(13) C16 0.0353(18) 0.0321(16) 0.0279(16) -0.0004(13) 0.0178(14) 0.0021(14) C17 0.056(2) 0.0430(19) 0.064(2) 0.0124(18) 0.047(2) 0.0105(18) C21 0.049(2) 0.046(2) 0.094(3) -0.001(2) 0.040(2) -0.0111(19) C22 0.070(3) 0.035(2) 0.061(2) -0.0051(18) 0.040(2) -0.0099(18) C23 0.076(3) 0.041(2) 0.052(2) 0.0072(17) 0.044(2) -0.0030(18) C24 0.070(3) 0.0373(19) 0.0348(19) 0.0092(16) 0.0204(18) 0.0026(18) C25 0.063(2) 0.047(2) 0.0282(18) -0.0045(15) 0.0173(17) 0.0035(18) C26 0.044(2) 0.048(2) 0.0383(19) -0.0013(16) 0.0120(17) 0.0057(17) N1 0.0402(16) 0.0308(13) 0.0438(16) -0.0045(13) 0.0268(13) -0.0052(12) N2 0.0484(17) 0.0322(14) 0.0277(14) 0.0018(11) 0.0189(13) 0.0030(12) O1 0.0285(11) 0.0470(13) 0.0288(11) -0.0035(10) 0.0156(9) -0.0036(10) O2 0.0350(12) 0.0314(11) 0.0269(11) 0.0052(9) 0.0190(10) 0.0017(9) O3 0.0289(11) 0.0297(11) 0.0316(11) 0.0059(9) 0.0147(9) 0.0013(9) O4 0.0375(12) 0.0331(12) 0.0347(12) 0.0047(10) 0.0242(10) 0.0009(10) Co1 0.0319(2) 0.0277(2) 0.0246(2) 0.00138(18) 0.01733(17) -0.00082(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.527(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.529(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.540(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.538(4) . ? C5 O1 1.269(3) . ? C5 C6 1.404(4) . ? C6 C7 1.390(4) . ? C6 H6 0.9500 . ? C7 O2 1.289(3) . ? C7 C8 1.494(4) . ? C8 C13 1.392(4) . ? C8 C9 1.396(4) . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 C11 1.389(4) . ? C10 C14 1.515(4) . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C12 C13 1.379(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.270(3) . ? C14 C15 1.402(4) . ? C15 C16 1.408(4) . ? C15 H15 0.9500 . ? C16 O4 1.266(4) . ? C16 C17 1.547(4) . ? C17 C19 1.423(9) . ? C17 C19A 1.446(9) . ? C17 C20 1.505(10) . ? C17 C20A 1.557(10) . ? C17 C18 1.621(9) . ? C17 C18A 1.647(9) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C18A H18D 0.9800 . ? C18A H18E 0.9800 . ? C18A H18F 0.9800 . ? C19A H19D 0.9800 . ? C19A H19E 0.9800 . ? C19A H19F 0.9800 . ? C20A H20D 0.9800 . ? C20A H20E 0.9800 . ? C20A H20F 0.9800 . ? C21 N1 1.462(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N1 1.472(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N1 1.484(4) . ? C23 C24 1.493(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N2 1.475(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N2 1.469(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N2 1.486(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 Co1 2.191(3) . ? N2 Co1 2.207(3) . ? O1 Co1 2.054(2) . ? O2 Co1 2.0432(19) . ? O3 Co1 2.054(2) 7_655 ? O4 Co1 2.052(2) 7_655 ? Co1 O4 2.052(2) 7_655 ? Co1 O3 2.054(2) 7_655 ? 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 C2 109.7(3) . . ? C1 C4 C5 109.8(3) . . ? C2 C4 C5 108.2(3) . . ? C1 C4 C3 108.6(3) . . ? C2 C4 C3 110.5(3) . . ? C5 C4 C3 110.1(3) . . ? O1 C5 C6 124.1(3) . . ? O1 C5 C4 116.9(3) . . ? C6 C5 C4 119.0(3) . . ? C7 C6 C5 126.0(3) . . ? C7 C6 H6 117.0 . . ? C5 C6 H6 117.0 . . ? O2 C7 C6 125.2(3) . . ? O2 C7 C8 115.4(3) . . ? C6 C7 C8 119.3(2) . . ? C13 C8 C9 118.3(3) . . ? C13 C8 C7 120.2(3) . . ? C9 C8 C7 121.4(3) . . ? C10 C9 C8 121.9(3) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C9 C10 C11 118.7(3) . . ? C9 C10 C14 118.0(2) . . ? C11 C10 C14 123.3(3) . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 120.5(3) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? O3 C14 C15 124.5(3) . . ? O3 C14 C10 115.1(2) . . ? C15 C14 C10 120.4(3) . . ? C14 C15 C16 124.4(3) . . ? C14 C15 H15 117.8 . . ? C16 C15 H15 117.8 . . ? O4 C16 C15 124.6(3) . . ? O4 C16 C17 115.1(3) . . ? C15 C16 C17 120.4(3) . . ? C19 C17 C19A 82.2(5) . . ? C19 C17 C20 106.8(5) . . ? C19A C17 C20 123.2(6) . . ? C19 C17 C16 111.6(4) . . ? C19A C17 C16 111.7(4) . . ? C20 C17 C16 115.7(4) . . ? C19 C17 C20A 124.0(6) . . ? C19A C17 C20A 110.4(5) . . ? C16 C17 C20A 112.8(4) . . ? C19 C17 C18 108.2(5) . . ? C20 C17 C18 110.1(5) . . ? C16 C17 C18 104.3(4) . . ? C20A C17 C18 92.1(5) . . ? C19A C17 C18A 106.2(5) . . ? C20 C17 C18A 92.0(5) . . ? C16 C17 C18A 103.1(4) . . ? C20A C17 C18A 112.2(5) . . ? C18 C17 C18A 132.0(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? C17 C18A H18D 109.5 . . ? C17 C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17 C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? C17 C19A H19D 109.5 . . ? C17 C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C17 C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C17 C20A H20D 109.5 . . ? C17 C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C17 C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? N1 C21 H21A 109.5 . . ? N1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 C24 111.4(3) . . ? N1 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? N1 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? N2 C24 C23 110.9(3) . . ? N2 C24 H24A 109.5 . . ? C23 C24 H24A 109.5 . . ? N2 C24 H24B 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.0 . . ? N2 C25 H25A 109.5 . . ? N2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 N1 C22 108.1(3) . . ? C21 N1 C23 109.5(3) . . ? C22 N1 C23 110.6(3) . . ? C21 N1 Co1 112.8(2) . . ? C22 N1 Co1 110.94(19) . . ? C23 N1 Co1 104.94(19) . . ? C25 N2 C24 112.0(3) . . ? C25 N2 C26 108.2(3) . . ? C24 N2 C26 108.3(3) . . ? C25 N2 Co1 112.2(2) . . ? C24 N2 Co1 104.3(2) . . ? C26 N2 Co1 111.77(18) . . ? C5 O1 Co1 124.26(19) . . ? C7 O2 Co1 122.04(18) . . ? C14 O3 Co1 121.55(18) . 7_655 ? C16 O4 Co1 125.43(18) . 7_655 ? O2 Co1 O4 175.52(8) . 7_655 ? O2 Co1 O1 87.54(8) . . ? O4 Co1 O1 91.62(8) 7_655 . ? O2 Co1 O3 89.57(8) . 7_655 ? O4 Co1 O3 86.03(8) 7_655 7_655 ? O1 Co1 O3 89.79(8) . 7_655 ? O2 Co1 N1 93.73(9) . . ? O4 Co1 N1 90.68(8) 7_655 . ? O1 Co1 N1 90.96(9) . . ? O3 Co1 N1 176.65(9) 7_655 . ? O2 Co1 N2 87.68(9) . . ? O4 Co1 N2 93.65(9) 7_655 . ? O1 Co1 N2 171.80(9) . . ? O3 Co1 N2 96.83(9) 7_655 . ? N1 Co1 N2 82.71(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C4 C5 O1 8.1(4) . . . . ? C2 C4 C5 O1 -111.6(3) . . . . ? C3 C4 C5 O1 127.6(3) . . . . ? C1 C4 C5 C6 -173.8(3) . . . . ? C2 C4 C5 C6 66.6(4) . . . . ? C3 C4 C5 C6 -54.3(4) . . . . ? O1 C5 C6 C7 4.3(5) . . . . ? C4 C5 C6 C7 -173.8(3) . . . . ? C5 C6 C7 O2 -0.4(5) . . . . ? C5 C6 C7 C8 178.7(3) . . . . ? O2 C7 C8 C13 32.3(4) . . . . ? C6 C7 C8 C13 -146.9(3) . . . . ? O2 C7 C8 C9 -145.7(3) . . . . ? C6 C7 C8 C9 35.1(4) . . . . ? C13 C8 C9 C10 1.0(4) . . . . ? C7 C8 C9 C10 178.9(2) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C8 C9 C10 C14 -178.2(2) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C14 C10 C11 C12 177.9(3) . . . . ? C10 C11 C12 C13 -0.6(5) . . . . ? C11 C12 C13 C8 0.7(5) . . . . ? C9 C8 C13 C12 -0.9(5) . . . . ? C7 C8 C13 C12 -178.9(3) . . . . ? C9 C10 C14 O3 4.8(4) . . . . ? C11 C10 C14 O3 -172.5(3) . . . . ? C9 C10 C14 C15 -173.7(3) . . . . ? C11 C10 C14 C15 9.0(4) . . . . ? O3 C14 C15 C16 5.6(5) . . . . ? C10 C14 C15 C16 -176.0(3) . . . . ? C14 C15 C16 O4 7.6(5) . . . . ? C14 C15 C16 C17 -172.7(3) . . . . ? O4 C16 C17 C19 56.9(5) . . . . ? C15 C16 C17 C19 -122.8(5) . . . . ? O4 C16 C17 C19A -33.1(6) . . . . ? C15 C16 C17 C19A 147.2(5) . . . . ? O4 C16 C17 C20 179.2(4) . . . . ? C15 C16 C17 C20 -0.4(6) . . . . ? O4 C16 C17 C20A -158.2(4) . . . . ? C15 C16 C17 C20A 22.1(5) . . . . ? O4 C16 C17 C18 -59.7(5) . . . . ? C15 C16 C17 C18 120.6(4) . . . . ? O4 C16 C17 C18A 80.5(4) . . . . ? C15 C16 C17 C18A -99.2(4) . . . . ? N1 C23 C24 N2 59.6(4) . . . . ? C24 C23 N1 C21 -161.5(3) . . . . ? C24 C23 N1 C22 79.5(3) . . . . ? C24 C23 N1 Co1 -40.2(3) . . . . ? C23 C24 N2 C25 78.4(3) . . . . ? C23 C24 N2 C26 -162.3(3) . . . . ? C23 C24 N2 Co1 -43.2(3) . . . . ? C6 C5 O1 Co1 18.3(4) . . . . ? C4 C5 O1 Co1 -163.6(2) . . . . ? C6 C7 O2 Co1 -24.9(4) . . . . ? C8 C7 O2 Co1 156.02(19) . . . . ? C15 C14 O3 Co1 -35.2(4) . . . 7_655 ? C10 C14 O3 Co1 146.39(18) . . . 7_655 ? C15 C16 O4 Co1 12.0(4) . . . 7_655 ? C17 C16 O4 Co1 -167.6(2) . . . 7_655 ? C7 O2 Co1 O1 33.1(2) . . . . ? C7 O2 Co1 O3 -56.7(2) . . . 7_655 ? C7 O2 Co1 N1 123.9(2) . . . . ? C7 O2 Co1 N2 -153.5(2) . . . . ? C5 O1 Co1 O2 -30.6(2) . . . . ? C5 O1 Co1 O4 145.0(2) . . . 7_655 ? C5 O1 Co1 O3 59.0(2) . . . 7_655 ? C5 O1 Co1 N1 -124.3(2) . . . . ? C21 N1 Co1 O2 -141.3(2) . . . . ? C22 N1 Co1 O2 -19.9(2) . . . . ? C23 N1 Co1 O2 99.6(2) . . . . ? C21 N1 Co1 O4 37.9(2) . . . 7_655 ? C22 N1 Co1 O4 159.4(2) . . . 7_655 ? C23 N1 Co1 O4 -81.2(2) . . . 7_655 ? C21 N1 Co1 O1 -53.7(2) . . . . ? C22 N1 Co1 O1 67.7(2) . . . . ? C23 N1 Co1 O1 -172.8(2) . . . . ? C21 N1 Co1 N2 131.5(2) . . . . ? C22 N1 Co1 N2 -107.0(2) . . . . ? C23 N1 Co1 N2 12.4(2) . . . . ? C25 N2 Co1 O2 160.6(2) . . . . ? C24 N2 Co1 O2 -78.0(2) . . . . ? C26 N2 Co1 O2 38.8(2) . . . . ? C25 N2 Co1 O4 -15.1(2) . . . 7_655 ? C24 N2 Co1 O4 106.3(2) . . . 7_655 ? C26 N2 Co1 O4 -136.9(2) . . . 7_655 ? C25 N2 Co1 O3 71.4(2) . . . 7_655 ? C24 N2 Co1 O3 -167.3(2) . . . 7_655 ? C26 N2 Co1 O3 -50.5(2) . . . 7_655 ? C25 N2 Co1 N1 -105.3(2) . . . . ? C24 N2 Co1 N1 16.1(2) . . . . ? C26 N2 Co1 N1 132.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.522 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.076 # Attachment 'Fig_6_Ni.CIF' data_lj254sad _database_code_depnum_ccdc_archive 'CCDC 754710' #TrackingRef 'Fig_6_Ni.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H80 N4 Ni2 O8' _chemical_formula_sum 'C52 H80 N4 Ni2 O8' _chemical_formula_weight 1006.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' #_symmetry_international_tables_no '15' 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 29.799(5) _cell_length_b 10.3542(15) _cell_length_c 19.542(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.693(11) _cell_angle_gamma 90.00 _cell_volume 5478.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1877 _cell_measurement_theta_min 2.720 _cell_measurement_theta_max 19.890 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.190 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32516 _diffrn_reflns_av_R_equivalents 0.1695 _diffrn_reflns_av_sigmaI/netI 0.1391 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4820 _reflns_number_gt 2550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0616P)^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 4820 _refine_ls_number_parameters 296 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1494 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.53673(19) 0.1915(6) 0.3854(3) 0.0554(10) Uani 1 1 d . . . H1A H 0.5262 0.1230 0.4101 0.083 Uiso 1 1 calc R . . H1B H 0.5101 0.2100 0.3359 0.083 Uiso 1 1 calc R . . H1C H 0.5444 0.2697 0.4164 0.083 Uiso 1 1 calc R . . C2 C 0.5703(2) 0.0304(6) 0.3228(3) 0.0554(10) Uani 1 1 d . . . H2A H 0.6004 -0.0002 0.3191 0.083 Uiso 1 1 calc R . . H2B H 0.5459 0.0554 0.2727 0.083 Uiso 1 1 calc R . . H2C H 0.5568 -0.0388 0.3428 0.083 Uiso 1 1 calc R . . C3 C 0.6003(2) 0.2606(6) 0.3422(3) 0.0554(10) Uani 1 1 d . . . H3A H 0.6107 0.3322 0.3783 0.083 Uiso 1 1 calc R . . H3B H 0.5733 0.2891 0.2953 0.083 Uiso 1 1 calc R . . H3C H 0.6283 0.2326 0.3318 0.083 Uiso 1 1 calc R . . C4 C 0.58274(18) 0.1474(5) 0.3755(3) 0.0355(13) Uani 1 1 d . . . C5 C 0.62353(17) 0.1080(5) 0.4519(3) 0.0321(12) Uani 1 1 d . . . C6 C 0.67069(16) 0.0755(4) 0.4554(3) 0.0267(11) Uani 1 1 d . . . H6 H 0.6759 0.0877 0.4111 0.032 Uiso 1 1 calc R . . C7 C 0.71004(17) 0.0272(4) 0.5190(3) 0.0267(11) Uani 1 1 d . . . C8 C 0.75777(16) -0.0029(4) 0.5138(2) 0.0208(11) Uani 1 1 d . . . C9 C 0.77511(16) 0.0716(4) 0.4713(2) 0.0211(10) Uani 1 1 d . . . H9 H 0.7557 0.1425 0.4438 0.025 Uiso 1 1 calc R . . C10 C 0.82019(16) 0.0472(4) 0.4671(2) 0.0221(11) Uani 1 1 d . . . C11 C 0.84813(17) -0.0568(4) 0.5083(3) 0.0307(12) Uani 1 1 d . . . H11 H 0.8792 -0.0753 0.5077 0.037 Uiso 1 1 calc R . . C12 C 0.83064(19) -0.1341(4) 0.5507(3) 0.0384(14) Uani 1 1 d . . . H12 H 0.8495 -0.2062 0.5776 0.046 Uiso 1 1 calc R . . C13 C 0.78636(18) -0.1064(4) 0.5537(3) 0.0338(12) Uani 1 1 d . . . H13 H 0.7752 -0.1587 0.5834 0.041 Uiso 1 1 calc R . . C14 C 0.83693(17) 0.1377(4) 0.4220(2) 0.0242(11) Uani 1 1 d . . . C15 C 0.87892(17) 0.1092(4) 0.4095(2) 0.0279(11) Uani 1 1 d . . . H15 H 0.8945 0.0282 0.4271 0.033 Uiso 1 1 calc R . . C16 C 0.89974(16) 0.1904(5) 0.3734(3) 0.0287(12) Uani 1 1 d . A . C17 C 0.94261(19) 0.1428(4) 0.3545(3) 0.0423(14) Uani 1 1 d D . . C18 C 0.9409(5) 0.2006(14) 0.2818(6) 0.072(2) Uani 0.50 1 d PD A 1 H18A H 0.9373 0.2945 0.2827 0.109 Uiso 0.50 1 calc PR A 1 H18B H 0.9128 0.1644 0.2388 0.109 Uiso 0.50 1 calc PR A 1 H18C H 0.9716 0.1799 0.2771 0.109 Uiso 0.50 1 calc PR A 1 C19 C 0.9459(6) -0.0037(7) 0.3548(11) 0.072(2) Uani 0.50 1 d PD A 1 H19A H 0.9159 -0.0390 0.3147 0.109 Uiso 0.50 1 calc PR A 1 H19B H 0.9491 -0.0369 0.4036 0.109 Uiso 0.50 1 calc PR A 1 H19C H 0.9747 -0.0297 0.3462 0.109 Uiso 0.50 1 calc PR A 1 C20 C 0.9890(4) 0.1988(13) 0.4182(6) 0.072(2) Uani 0.50 1 d PD A 1 H20A H 1.0176 0.1857 0.4064 0.109 Uiso 0.50 1 calc PR A 1 H20B H 0.9947 0.1551 0.4656 0.109 Uiso 0.50 1 calc PR A 1 H20C H 0.9844 0.2915 0.4232 0.109 Uiso 0.50 1 calc PR A 1 C18A C 0.9231(5) 0.1502(15) 0.2686(5) 0.072(2) Uani 0.50 1 d PD A 2 H18D H 0.9128 0.2389 0.2520 0.109 Uiso 0.50 1 calc PR A 2 H18E H 0.8948 0.0920 0.2455 0.109 Uiso 0.50 1 calc PR A 2 H18F H 0.9493 0.1244 0.2534 0.109 Uiso 0.50 1 calc PR A 2 C19A C 0.9597(6) 0.0044(8) 0.3784(11) 0.072(2) Uani 0.50 1 d PD A 2 H19D H 0.9309 -0.0528 0.3619 0.109 Uiso 0.50 1 calc PR A 2 H19E H 0.9775 0.0004 0.4333 0.109 Uiso 0.50 1 calc PR A 2 H19F H 0.9816 -0.0231 0.3551 0.109 Uiso 0.50 1 calc PR A 2 C20A C 0.9865(4) 0.2339(12) 0.3898(7) 0.072(2) Uani 0.50 1 d PD A 2 H20D H 1.0151 0.1975 0.3840 0.109 Uiso 0.50 1 calc PR A 2 H20E H 0.9945 0.2447 0.4435 0.109 Uiso 0.50 1 calc PR A 2 H20F H 0.9782 0.3180 0.3646 0.109 Uiso 0.50 1 calc PR A 2 C21 C 0.6386(2) -0.1913(5) 0.5887(3) 0.0514(16) Uani 1 1 d . . . H21A H 0.6241 -0.2710 0.5975 0.077 Uiso 1 1 calc R . . H21B H 0.6743 -0.2031 0.6056 0.077 Uiso 1 1 calc R . . H21C H 0.6236 -0.1709 0.5348 0.077 Uiso 1 1 calc R . . C22 C 0.57591(19) -0.0773(5) 0.6075(4) 0.0582(17) Uani 1 1 d . . . H22A H 0.5596 -0.0527 0.5542 0.087 Uiso 1 1 calc R . . H22B H 0.5690 -0.0122 0.6382 0.087 Uiso 1 1 calc R . . H22C H 0.5634 -0.1614 0.6146 0.087 Uiso 1 1 calc R . . C23 C 0.6542(2) -0.1091(5) 0.7132(3) 0.0514(16) Uani 1 1 d . . . H23A H 0.6370 -0.0589 0.7381 0.062 Uiso 1 1 calc R . . H23B H 0.6513 -0.2017 0.7232 0.062 Uiso 1 1 calc R . . C24 C 0.7066(2) -0.0728(5) 0.7462(3) 0.0476(15) Uani 1 1 d . . . H24A H 0.7246 -0.1289 0.7251 0.057 Uiso 1 1 calc R . . H24B H 0.7207 -0.0871 0.8013 0.057 Uiso 1 1 calc R . . C25 C 0.76529(18) 0.0821(5) 0.7402(3) 0.0444(14) Uani 1 1 d . . . H25A H 0.7880 0.0702 0.7932 0.067 Uiso 1 1 calc R . . H25B H 0.7691 0.1696 0.7242 0.067 Uiso 1 1 calc R . . H25C H 0.7729 0.0189 0.7092 0.067 Uiso 1 1 calc R . . C26 C 0.70529(19) 0.1499(5) 0.7852(3) 0.0393(14) Uani 1 1 d . . . H26A H 0.6723 0.1344 0.7829 0.059 Uiso 1 1 calc R . . H26B H 0.7080 0.2401 0.7721 0.059 Uiso 1 1 calc R . . H26C H 0.7302 0.1323 0.8362 0.059 Uiso 1 1 calc R . . N1 N 0.62960(14) -0.0859(4) 0.6306(2) 0.0332(10) Uani 1 1 d . . . N2 N 0.71361(14) 0.0633(3) 0.7310(2) 0.0290(10) Uani 1 1 d . . . O1 O 0.61200(10) 0.1022(3) 0.50738(16) 0.0291(8) Uani 1 1 d . . . O2 O 0.70904(10) 0.0020(3) 0.58267(17) 0.0254(8) Uani 1 1 d . . . O3 O 0.80956(11) 0.2365(3) 0.39559(17) 0.0264(8) Uani 1 1 d . . . O4 O 0.88570(11) 0.3050(3) 0.35256(17) 0.0282(8) Uani 1 1 d . . . Ni1 Ni 0.66115(2) 0.09259(5) 0.61642(3) 0.02370(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.040(2) 0.086(3) 0.031(2) -0.0001(18) 0.0058(17) 0.0090(18) C2 0.040(2) 0.086(3) 0.031(2) -0.0001(18) 0.0058(17) 0.0090(18) C3 0.040(2) 0.086(3) 0.031(2) -0.0001(18) 0.0058(17) 0.0090(18) C4 0.030(3) 0.055(3) 0.018(3) 0.000(2) 0.007(2) 0.005(2) C5 0.034(3) 0.038(3) 0.030(3) -0.006(2) 0.019(3) -0.002(2) C6 0.029(3) 0.034(3) 0.023(3) 0.000(2) 0.017(2) -0.001(2) C7 0.036(3) 0.025(3) 0.028(3) -0.006(2) 0.021(3) -0.008(2) C8 0.031(3) 0.017(2) 0.018(3) -0.004(2) 0.014(2) 0.001(2) C9 0.024(3) 0.019(3) 0.020(3) -0.004(2) 0.009(2) 0.000(2) C10 0.027(3) 0.023(3) 0.022(3) -0.002(2) 0.016(2) 0.000(2) C11 0.032(3) 0.032(3) 0.038(3) 0.003(2) 0.024(3) 0.003(2) C12 0.048(4) 0.028(3) 0.054(4) 0.018(2) 0.036(3) 0.019(2) C13 0.050(3) 0.029(3) 0.035(3) 0.009(2) 0.030(3) -0.003(3) C14 0.029(3) 0.026(3) 0.022(3) -0.005(2) 0.014(2) -0.004(2) C15 0.036(3) 0.026(3) 0.032(3) 0.009(2) 0.025(2) 0.008(2) C16 0.025(3) 0.038(3) 0.028(3) -0.002(2) 0.016(2) -0.001(2) C17 0.048(4) 0.039(3) 0.061(4) 0.009(3) 0.043(3) 0.007(3) C18 0.065(5) 0.079(4) 0.111(6) 0.019(3) 0.073(4) 0.020(3) C19 0.065(5) 0.079(4) 0.111(6) 0.019(3) 0.073(4) 0.020(3) C20 0.065(5) 0.079(4) 0.111(6) 0.019(3) 0.073(4) 0.020(3) C18A 0.065(5) 0.079(4) 0.111(6) 0.019(3) 0.073(4) 0.020(3) C19A 0.065(5) 0.079(4) 0.111(6) 0.019(3) 0.073(4) 0.020(3) C20A 0.065(5) 0.079(4) 0.111(6) 0.019(3) 0.073(4) 0.020(3) C21 0.068(4) 0.038(3) 0.073(4) -0.010(3) 0.053(4) -0.009(3) C22 0.045(4) 0.048(4) 0.090(5) -0.008(3) 0.037(4) -0.012(3) C23 0.069(4) 0.036(3) 0.062(4) 0.018(3) 0.041(4) -0.002(3) C24 0.073(4) 0.028(3) 0.036(3) 0.009(2) 0.017(3) -0.003(3) C25 0.046(4) 0.049(3) 0.030(3) -0.006(3) 0.007(3) 0.008(3) C26 0.049(4) 0.046(3) 0.023(3) -0.008(2) 0.016(3) 0.008(3) N1 0.040(3) 0.032(2) 0.038(3) -0.006(2) 0.026(2) -0.005(2) N2 0.041(3) 0.025(2) 0.023(2) 0.0013(17) 0.016(2) 0.0018(18) O1 0.0244(18) 0.0423(19) 0.0250(19) -0.0033(16) 0.0146(15) -0.0033(15) O2 0.0290(19) 0.0266(18) 0.0272(19) 0.0042(14) 0.0182(16) 0.0018(14) O3 0.0236(19) 0.0291(19) 0.0294(19) 0.0061(15) 0.0139(16) 0.0047(15) O4 0.036(2) 0.0266(19) 0.0295(19) 0.0059(15) 0.0207(16) 0.0019(15) Ni1 0.0294(4) 0.0251(3) 0.0236(3) 0.0007(3) 0.0179(3) -0.0016(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 C1 C4 1.532(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.533(7) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.535(7) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.535(6) . ? C5 O1 1.268(5) . ? C5 C6 1.418(6) . ? C6 C7 1.396(6) . ? C6 H6 0.9500 . ? C7 O2 1.285(5) . ? C7 C8 1.500(6) . ? C8 C9 1.382(6) . ? C8 C13 1.389(6) . ? C9 C10 1.403(6) . ? C9 H9 0.9500 . ? C10 C11 1.394(6) . ? C10 C14 1.507(6) . ? C11 C12 1.400(6) . ? C11 H11 0.9500 . ? C12 C13 1.375(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.275(5) . ? C14 C15 1.402(6) . ? C15 C16 1.399(6) . ? C15 H15 0.9500 . ? C16 O4 1.267(5) . ? C16 C17 1.550(6) . ? C17 C19 1.520(7) . ? C17 C20A 1.524(7) . ? C17 C18 1.524(7) . ? C17 C19A 1.526(7) . ? C17 C18A 1.532(7) . ? C17 C20 1.536(8) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C18A H18D 0.9800 . ? C18A H18E 0.9800 . ? C18A H18F 0.9800 . ? C19A H19D 0.9800 . ? C19A H19E 0.9800 . ? C19A H19F 0.9800 . ? C20A H20D 0.9800 . ? C20A H20E 0.9800 . ? C20A H20F 0.9800 . ? C21 N1 1.456(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N1 1.472(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.467(7) . ? C23 N1 1.488(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N2 1.473(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N2 1.487(6) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N2 1.485(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 Ni1 2.143(4) . ? N2 Ni1 2.151(4) . ? O1 Ni1 2.022(3) . ? O2 Ni1 2.034(3) . ? O3 Ni1 2.030(3) 7_656 ? O4 Ni1 2.037(3) 7_656 ? Ni1 O3 2.030(3) 7_656 ? Ni1 O4 2.037(3) 7_656 ? 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 C5 108.3(4) . . ? C2 C4 C1 110.0(4) . . ? C5 C4 C1 110.1(4) . . ? C2 C4 C3 110.3(4) . . ? C5 C4 C3 110.1(4) . . ? C1 C4 C3 107.9(4) . . ? O1 C5 C6 124.3(4) . . ? O1 C5 C4 117.2(4) . . ? C6 C5 C4 118.5(4) . . ? C7 C6 C5 125.1(4) . . ? C7 C6 H6 117.4 . . ? C5 C6 H6 117.4 . . ? O2 C7 C6 125.7(4) . . ? O2 C7 C8 115.4(4) . . ? C6 C7 C8 118.8(4) . . ? C9 C8 C13 118.2(4) . . ? C9 C8 C7 121.8(4) . . ? C13 C8 C7 119.9(4) . . ? C8 C9 C10 122.9(4) . . ? C8 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 117.4(4) . . ? C11 C10 C14 123.7(4) . . ? C9 C10 C14 118.8(4) . . ? C10 C11 C12 120.3(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 120.8(4) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? O3 C14 C15 124.4(4) . . ? O3 C14 C10 115.0(4) . . ? C15 C14 C10 120.5(4) . . ? C16 C15 C14 125.2(4) . . ? C16 C15 H15 117.4 . . ? C14 C15 H15 117.4 . . ? O4 C16 C15 124.6(4) . . ? O4 C16 C17 114.6(4) . . ? C15 C16 C17 120.8(4) . . ? C19 C17 C20A 125.0(10) . . ? C19 C17 C18 111.8(10) . . ? C20A C17 C18 82.3(8) . . ? C20A C17 C19A 109.2(9) . . ? C18 C17 C19A 122.0(11) . . ? C19 C17 C18A 92.7(10) . . ? C20A C17 C18A 109.0(7) . . ? C19A C17 C18A 107.8(10) . . ? C19 C17 C20 109.9(9) . . ? C18 C17 C20 106.0(8) . . ? C19A C17 C20 92.0(9) . . ? C18A C17 C20 132.1(8) . . ? C19 C17 C16 112.0(8) . . ? C20A C17 C16 109.5(6) . . ? C18 C17 C16 112.8(7) . . ? C19A C17 C16 115.4(8) . . ? C18A C17 C16 105.7(6) . . ? C20 C17 C16 103.9(6) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? C17 C18A H18D 109.5 . . ? C17 C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17 C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? C17 C19A H19D 109.5 . . ? C17 C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C17 C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C17 C20A H20D 109.5 . . ? C17 C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C17 C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? N1 C21 H21A 109.5 . . ? N1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 N1 112.8(4) . . ? C24 C23 H23A 109.0 . . ? N1 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? N1 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C23 C24 N2 111.7(4) . . ? C23 C24 H24A 109.3 . . ? N2 C24 H24A 109.3 . . ? C23 C24 H24B 109.3 . . ? N2 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? N2 C25 H25A 109.5 . . ? N2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 N1 C22 107.8(4) . . ? C21 N1 C23 111.5(4) . . ? C22 N1 C23 108.8(4) . . ? C21 N1 Ni1 112.3(3) . . ? C22 N1 Ni1 112.8(3) . . ? C23 N1 Ni1 103.6(3) . . ? C24 N2 C26 110.8(4) . . ? C24 N2 C25 109.1(4) . . ? C26 N2 C25 108.0(4) . . ? C24 N2 Ni1 104.0(3) . . ? C26 N2 Ni1 113.1(3) . . ? C25 N2 Ni1 111.9(3) . . ? C5 O1 Ni1 124.6(3) . . ? C7 O2 Ni1 121.6(3) . . ? C14 O3 Ni1 120.9(3) . 7_656 ? C16 O4 Ni1 124.6(3) . 7_656 ? O1 Ni1 O3 89.57(12) . 7_656 ? O1 Ni1 O2 88.77(12) . . ? O3 Ni1 O2 88.34(12) 7_656 . ? O1 Ni1 O4 90.19(12) . 7_656 ? O3 Ni1 O4 87.80(12) 7_656 7_656 ? O2 Ni1 O4 176.01(12) . 7_656 ? O1 Ni1 N1 90.84(14) . . ? O3 Ni1 N1 178.79(14) 7_656 . ? O2 Ni1 N1 92.81(13) . . ? O4 Ni1 N1 91.06(13) 7_656 . ? O1 Ni1 N2 174.68(13) . . ? O3 Ni1 N2 94.74(13) 7_656 . ? O2 Ni1 N2 88.25(13) . . ? O4 Ni1 N2 93.09(13) 7_656 . ? N1 Ni1 N2 84.92(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C4 C5 O1 -112.2(5) . . . . ? C1 C4 C5 O1 8.2(6) . . . . ? C3 C4 C5 O1 127.1(5) . . . . ? C2 C4 C5 C6 65.3(6) . . . . ? C1 C4 C5 C6 -174.3(4) . . . . ? C3 C4 C5 C6 -55.4(6) . . . . ? O1 C5 C6 C7 3.2(7) . . . . ? C4 C5 C6 C7 -174.1(4) . . . . ? C5 C6 C7 O2 1.9(7) . . . . ? C5 C6 C7 C8 179.9(4) . . . . ? O2 C7 C8 C9 -145.9(4) . . . . ? C6 C7 C8 C9 35.9(6) . . . . ? O2 C7 C8 C13 32.7(6) . . . . ? C6 C7 C8 C13 -145.5(4) . . . . ? C13 C8 C9 C10 -0.2(6) . . . . ? C7 C8 C9 C10 178.5(4) . . . . ? C8 C9 C10 C11 -0.4(6) . . . . ? C8 C9 C10 C14 -177.3(4) . . . . ? C9 C10 C11 C12 1.3(7) . . . . ? C14 C10 C11 C12 178.0(4) . . . . ? C10 C11 C12 C13 -1.7(7) . . . . ? C11 C12 C13 C8 1.1(8) . . . . ? C9 C8 C13 C12 -0.2(7) . . . . ? C7 C8 C13 C12 -178.9(4) . . . . ? C11 C10 C14 O3 -171.6(4) . . . . ? C9 C10 C14 O3 5.1(6) . . . . ? C11 C10 C14 C15 10.3(7) . . . . ? C9 C10 C14 C15 -173.0(4) . . . . ? O3 C14 C15 C16 6.9(8) . . . . ? C10 C14 C15 C16 -175.1(4) . . . . ? C14 C15 C16 O4 6.1(8) . . . . ? C14 C15 C16 C17 -173.0(4) . . . . ? O4 C16 C17 C19 -159.9(9) . . . . ? C15 C16 C17 C19 19.3(10) . . . . ? O4 C16 C17 C20A 57.0(7) . . . . ? C15 C16 C17 C20A -123.8(7) . . . . ? O4 C16 C17 C18 -32.7(8) . . . . ? C15 C16 C17 C18 146.5(7) . . . . ? O4 C16 C17 C19A -179.3(9) . . . . ? C15 C16 C17 C19A -0.2(10) . . . . ? O4 C16 C17 C18A -60.3(7) . . . . ? C15 C16 C17 C18A 118.9(7) . . . . ? O4 C16 C17 C20 81.6(7) . . . . ? C15 C16 C17 C20 -99.2(7) . . . . ? N1 C23 C24 N2 56.8(6) . . . . ? C24 C23 N1 C21 82.2(5) . . . . ? C24 C23 N1 C22 -159.0(4) . . . . ? C24 C23 N1 Ni1 -38.8(5) . . . . ? C23 C24 N2 C26 81.5(5) . . . . ? C23 C24 N2 C25 -159.8(4) . . . . ? C23 C24 N2 Ni1 -40.2(5) . . . . ? C6 C5 O1 Ni1 17.1(6) . . . . ? C4 C5 O1 Ni1 -165.6(3) . . . . ? C6 C7 O2 Ni1 -25.3(6) . . . . ? C8 C7 O2 Ni1 156.6(3) . . . . ? C15 C14 O3 Ni1 -34.4(6) . . . 7_656 ? C10 C14 O3 Ni1 147.5(3) . . . 7_656 ? C15 C16 O4 Ni1 11.7(6) . . . 7_656 ? C17 C16 O4 Ni1 -169.2(3) . . . 7_656 ? C5 O1 Ni1 O3 59.4(4) . . . 7_656 ? C5 O1 Ni1 O2 -28.9(4) . . . . ? C5 O1 Ni1 O4 147.2(4) . . . 7_656 ? C5 O1 Ni1 N1 -121.7(4) . . . . ? C7 O2 Ni1 O1 32.2(3) . . . . ? C7 O2 Ni1 O3 -57.4(3) . . . 7_656 ? C7 O2 Ni1 N1 123.0(3) . . . . ? C7 O2 Ni1 N2 -152.2(3) . . . . ? C21 N1 Ni1 O1 68.5(4) . . . . ? C22 N1 Ni1 O1 -53.5(3) . . . . ? C23 N1 Ni1 O1 -171.0(3) . . . . ? C21 N1 Ni1 O2 -20.3(4) . . . . ? C22 N1 Ni1 O2 -142.3(3) . . . . ? C23 N1 Ni1 O2 100.2(3) . . . . ? C21 N1 Ni1 O4 158.7(4) . . . 7_656 ? C22 N1 Ni1 O4 36.7(3) . . . 7_656 ? C23 N1 Ni1 O4 -80.8(3) . . . 7_656 ? C21 N1 Ni1 N2 -108.3(4) . . . . ? C22 N1 Ni1 N2 129.7(3) . . . . ? C23 N1 Ni1 N2 12.2(3) . . . . ? C24 N2 Ni1 O3 -166.8(3) . . . 7_656 ? C26 N2 Ni1 O3 73.0(3) . . . 7_656 ? C25 N2 Ni1 O3 -49.2(3) . . . 7_656 ? C24 N2 Ni1 O2 -78.6(3) . . . . ? C26 N2 Ni1 O2 161.2(3) . . . . ? C25 N2 Ni1 O2 39.0(3) . . . . ? C24 N2 Ni1 O4 105.2(3) . . . 7_656 ? C26 N2 Ni1 O4 -15.1(3) . . . 7_656 ? C25 N2 Ni1 O4 -137.2(3) . . . 7_656 ? C24 N2 Ni1 N1 14.4(3) . . . . ? C26 N2 Ni1 N1 -105.9(3) . . . . ? C25 N2 Ni1 N1 132.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.408 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.091 # Attachment 'Fig_7.CIF' data_lj250sad _database_code_depnum_ccdc_archive 'CCDC 754711' #TrackingRef 'Fig_7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H80 Cu2 N4 O8' _chemical_formula_sum 'C52 H80 Cu2 N4 O8' _chemical_formula_weight 1016.28 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-p 1' #_symmetry_international_tables_no '2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4163(10) _cell_length_b 10.5103(11) _cell_length_c 15.2349(16) _cell_angle_alpha 95.511(2) _cell_angle_beta 94.794(2) _cell_angle_gamma 115.995(2) _cell_volume 1335.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9274 _cell_measurement_theta_min 2.381 _cell_measurement_theta_max 28.364 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.450 _exptl_crystal_size_min 0.250 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542 _exptl_absorpt_coefficient_mu 0.850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.809 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 208 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.04 _diffrn_reflns_number 13260 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0210 _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 -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.36 _reflns_number_total 6212 _reflns_number_gt 5711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _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^)+(0.0595P)^2^+0.8582P] 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 6212 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4926(3) -0.1402(3) 0.3783(2) 0.0588(7) Uani 1 1 d . . . H1A H 0.5360 -0.1681 0.4297 0.088 Uiso 1 1 calc R . . H1B H 0.5213 -0.0379 0.3902 0.088 Uiso 1 1 calc R . . H1C H 0.5371 -0.1589 0.3255 0.088 Uiso 1 1 calc R . . C2 C 0.2663(3) -0.3862(2) 0.34207(15) 0.0418(5) Uani 1 1 d . . . H2A H 0.1499 -0.4422 0.3330 0.063 Uiso 1 1 calc R . . H2B H 0.3119 -0.4146 0.3923 0.063 Uiso 1 1 calc R . . H2C H 0.3086 -0.4041 0.2881 0.063 Uiso 1 1 calc R . . C3 C 0.2385(4) -0.2030(3) 0.44588(15) 0.0555(7) Uani 1 1 d . . . H3A H 0.1219 -0.2556 0.4337 0.083 Uiso 1 1 calc R . . H3B H 0.2705 -0.1007 0.4616 0.083 Uiso 1 1 calc R . . H3C H 0.2775 -0.2376 0.4955 0.083 Uiso 1 1 calc R . . C4 C 0.3106(3) -0.2271(2) 0.36204(13) 0.0349(4) Uani 1 1 d . . . C5 C 0.2454(2) -0.17084(19) 0.28760(12) 0.0262(3) Uani 1 1 d . A . C6 C 0.1406(2) -0.2644(2) 0.21358(12) 0.0291(4) Uani 1 1 d . . . H6 H 0.1191 -0.3622 0.2081 0.035 Uiso 1 1 calc R . . C7 C 0.0657(2) -0.22180(18) 0.14705(11) 0.0237(3) Uani 1 1 d . A . C8 C -0.0600(2) -0.33195(19) 0.07595(11) 0.0250(3) Uani 1 1 d . . . C9 C -0.1226(2) -0.28440(19) 0.00729(11) 0.0248(3) Uani 1 1 d . . . H9 H -0.0808 -0.1845 0.0055 0.030 Uiso 1 1 calc R . . C10 C -0.2452(2) -0.38002(19) -0.05895(11) 0.0265(3) Uani 1 1 d . . . C11 C -0.3046(3) -0.5266(2) -0.05612(13) 0.0358(4) Uani 1 1 d . . . H11 H -0.3885 -0.5932 -0.1003 0.043 Uiso 1 1 calc R . . C12 C -0.2413(3) -0.5753(2) 0.01101(14) 0.0407(5) Uani 1 1 d . . . H12 H -0.2815 -0.6752 0.0120 0.049 Uiso 1 1 calc R . . C13 C -0.1202(3) -0.4796(2) 0.07651(13) 0.0335(4) Uani 1 1 d . . . H13 H -0.0778 -0.5143 0.1220 0.040 Uiso 1 1 calc R . . C14 C -0.3038(2) -0.31959(19) -0.13120(11) 0.0250(3) Uani 1 1 d . . . C15 C -0.4459(2) -0.4072(2) -0.18869(12) 0.0286(4) Uani 1 1 d . . . H15 H -0.5079 -0.5018 -0.1771 0.034 Uiso 1 1 calc R . . C16 C -0.50079(19) -0.36255(19) -0.26193(11) 0.0247(3) Uani 1 1 d . . . C17 C -0.6551(2) -0.4648(2) -0.32412(12) 0.0305(4) Uani 1 1 d . . . C18 C -0.6105(3) -0.4775(3) -0.41814(13) 0.0426(5) Uani 1 1 d . . . H18A H -0.5376 -0.5214 -0.4185 0.064 Uiso 1 1 calc R . . H18B H -0.5580 -0.3820 -0.4356 0.064 Uiso 1 1 calc R . . H18C H -0.7073 -0.5372 -0.4603 0.064 Uiso 1 1 calc R . . C19 C -0.7362(2) -0.6144(2) -0.29800(15) 0.0397(5) Uani 1 1 d . . . H19A H -0.6636 -0.6584 -0.2998 0.059 Uiso 1 1 calc R . . H19B H -0.8337 -0.6733 -0.3398 0.059 Uiso 1 1 calc R . . H19C H -0.7635 -0.6075 -0.2376 0.059 Uiso 1 1 calc R . . C20 C -0.7688(2) -0.3962(3) -0.32375(16) 0.0434(5) Uani 1 1 d . . . H20A H -0.8653 -0.4557 -0.3662 0.065 Uiso 1 1 calc R . . H20B H -0.7160 -0.3006 -0.3409 0.065 Uiso 1 1 calc R . . H20C H -0.7979 -0.3885 -0.2639 0.065 Uiso 1 1 calc R . . C21 C 0.0725(5) 0.0613(5) 0.3982(3) 0.0371(3) Uani 0.50 1 d P A 1 H21A H 0.0054 0.0820 0.4373 0.056 Uiso 0.50 1 calc PR A 1 H21B H 0.1845 0.1135 0.4253 0.056 Uiso 0.50 1 calc PR A 1 H21C H 0.0406 -0.0417 0.3899 0.056 Uiso 0.50 1 calc PR A 1 C22 C 0.1024(5) 0.2613(5) 0.3266(3) 0.0371(3) Uani 0.50 1 d P A 1 H22A H 0.0342 0.2793 0.3661 0.056 Uiso 0.50 1 calc PR A 1 H22B H 0.0931 0.2973 0.2705 0.056 Uiso 0.50 1 calc PR A 1 H22C H 0.2136 0.3104 0.3553 0.056 Uiso 0.50 1 calc PR A 1 C23 C -0.1169(5) 0.0272(5) 0.2717(3) 0.0371(3) Uani 0.50 1 d P A 1 H23A H -0.1791 0.0613 0.3082 0.045 Uiso 0.50 1 calc PR A 1 H23B H -0.1522 -0.0751 0.2771 0.045 Uiso 0.50 1 calc PR A 1 C24 C -0.1554(11) 0.0390(7) 0.1760(7) 0.0371(3) Uani 0.50 1 d P A 1 H24A H -0.1189 0.1414 0.1706 0.045 Uiso 0.50 1 calc PR A 1 H24B H -0.0938 0.0041 0.1396 0.045 Uiso 0.50 1 calc PR A 1 C25 C -0.3022(5) 0.0045(5) 0.0319(3) 0.0371(3) Uani 0.50 1 d P A 1 H25A H -0.3240 0.0867 0.0269 0.056 Uiso 0.50 1 calc PR A 1 H25B H -0.3814 -0.0787 -0.0094 0.056 Uiso 0.50 1 calc PR A 1 H25C H -0.1952 0.0272 0.0171 0.056 Uiso 0.50 1 calc PR A 1 C26 C -0.4243(6) 0.0116(5) 0.1693(4) 0.0371(3) Uani 0.50 1 d P A 1 H26A H -0.4200 0.0171 0.2341 0.056 Uiso 0.50 1 calc PR A 1 H26B H -0.5319 -0.0566 0.1406 0.056 Uiso 0.50 1 calc PR A 1 H26C H -0.3983 0.1063 0.1526 0.056 Uiso 0.50 1 calc PR A 1 N2 N -0.3128(4) -0.0345(4) 0.1413(2) 0.0314(6) Uiso 0.50 1 d P A 1 N2A N -0.2586(6) 0.0825(5) 0.1233(3) 0.0565(11) Uiso 0.50 1 d P A 2 C21A C 0.1460(5) 0.2187(5) 0.3818(3) 0.0371(3) Uani 0.50 1 d P A 2 H21D H 0.0754 0.2295 0.4225 0.056 Uiso 0.50 1 calc PR A 2 H21E H 0.2041 0.3091 0.3591 0.056 Uiso 0.50 1 calc PR A 2 H21F H 0.2222 0.1930 0.4137 0.056 Uiso 0.50 1 calc PR A 2 C22A C -0.0358(5) -0.0270(5) 0.3392(3) 0.0371(3) Uani 0.50 1 d P A 2 H22D H 0.0375 -0.0494 0.3767 0.056 Uiso 0.50 1 calc PR A 2 H22E H -0.0888 -0.1027 0.2879 0.056 Uiso 0.50 1 calc PR A 2 H22F H -0.1161 -0.0207 0.3739 0.056 Uiso 0.50 1 calc PR A 2 C23A C -0.0567(5) 0.1518(5) 0.2573(3) 0.0371(3) Uani 0.50 1 d P A 2 H23C H -0.1322 0.1589 0.2967 0.045 Uiso 0.50 1 calc PR A 2 H23D H 0.0081 0.2489 0.2430 0.045 Uiso 0.50 1 calc PR A 2 C24A C -0.1484(12) 0.0603(7) 0.1756(7) 0.0371(3) Uani 0.50 1 d P A 2 H24C H -0.0701 0.0576 0.1368 0.045 Uiso 0.50 1 calc PR A 2 H24D H -0.2052 -0.0373 0.1910 0.045 Uiso 0.50 1 calc PR A 2 C25A C -0.4009(6) 0.0621(5) 0.1655(4) 0.0371(3) Uani 0.50 1 d P A 2 H25D H -0.4702 -0.0405 0.1629 0.056 Uiso 0.50 1 calc PR A 2 H25E H -0.4592 0.1055 0.1338 0.056 Uiso 0.50 1 calc PR A 2 H25F H -0.3679 0.1077 0.2278 0.056 Uiso 0.50 1 calc PR A 2 C26A C -0.3349(5) -0.0609(5) 0.0450(3) 0.0371(3) Uani 0.50 1 d P A 2 H26D H -0.2510 -0.0610 0.0111 0.056 Uiso 0.50 1 calc PR A 2 H26E H -0.4201 -0.0584 0.0048 0.056 Uiso 0.50 1 calc PR A 2 H26F H -0.3786 -0.1478 0.0731 0.056 Uiso 0.50 1 calc PR A 2 N1 N 0.05236(17) 0.10771(15) 0.30850(10) 0.0250(3) Uani 1 1 d . . . O1 O 0.29063(16) -0.03654(14) 0.30133(8) 0.0286(3) Uani 1 1 d . . . O2 O 0.09292(15) -0.09299(14) 0.14237(8) 0.0278(3) Uani 1 1 d . . . O3 O -0.21497(15) -0.18818(13) -0.13509(8) 0.0268(3) Uani 1 1 d . . . O4 O -0.43078(15) -0.23925(14) -0.28521(8) 0.0283(3) Uani 1 1 d . . . Cu1 Cu 0.24279(2) 0.07648(2) 0.222297(13) 0.02320(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0444(13) 0.0462(13) 0.0761(18) 0.0091(12) -0.0309(12) 0.0185(11) C2 0.0558(13) 0.0340(10) 0.0379(11) -0.0005(8) -0.0141(9) 0.0269(10) C3 0.098(2) 0.0582(15) 0.0255(10) 0.0049(10) -0.0013(11) 0.0502(16) C4 0.0438(11) 0.0311(10) 0.0290(9) -0.0016(7) -0.0110(8) 0.0202(9) C5 0.0282(8) 0.0295(9) 0.0239(8) 0.0008(7) -0.0024(7) 0.0173(7) C6 0.0354(9) 0.0262(8) 0.0260(8) -0.0010(7) -0.0063(7) 0.0169(7) C7 0.0251(8) 0.0253(8) 0.0212(8) -0.0010(6) -0.0004(6) 0.0135(7) C8 0.0269(8) 0.0259(8) 0.0201(8) -0.0001(6) -0.0004(6) 0.0114(7) C9 0.0250(8) 0.0246(8) 0.0217(8) 0.0003(6) -0.0005(6) 0.0096(7) C10 0.0256(8) 0.0284(9) 0.0196(8) 0.0017(6) -0.0003(6) 0.0078(7) C11 0.0384(10) 0.0275(9) 0.0254(9) 0.0012(7) -0.0068(8) 0.0029(8) C12 0.0508(12) 0.0238(9) 0.0325(10) 0.0041(8) -0.0076(9) 0.0056(9) C13 0.0424(11) 0.0285(9) 0.0245(9) 0.0038(7) -0.0036(8) 0.0129(8) C14 0.0230(8) 0.0291(8) 0.0185(7) 0.0006(6) 0.0005(6) 0.0089(7) C15 0.0239(8) 0.0300(9) 0.0225(8) 0.0015(7) -0.0012(6) 0.0049(7) C16 0.0189(7) 0.0309(9) 0.0200(8) -0.0022(6) 0.0004(6) 0.0088(7) C17 0.0205(8) 0.0365(10) 0.0248(8) -0.0011(7) -0.0037(6) 0.0065(7) C18 0.0376(11) 0.0507(13) 0.0227(9) -0.0051(8) -0.0051(8) 0.0085(10) C19 0.0286(9) 0.0359(11) 0.0368(11) -0.0006(8) -0.0066(8) 0.0017(8) C20 0.0230(9) 0.0513(13) 0.0503(13) 0.0028(10) -0.0054(8) 0.0144(9) C21 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C22 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C23 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C24 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C25 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C26 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C21A 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C22A 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C23A 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C24A 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C25A 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) C26A 0.0331(6) 0.0390(8) 0.0412(6) 0.0021(6) 0.0036(5) 0.0191(6) N1 0.0245(7) 0.0207(7) 0.0291(7) 0.0027(6) 0.0012(6) 0.0102(6) O1 0.0333(7) 0.0278(6) 0.0241(6) -0.0023(5) -0.0077(5) 0.0165(5) O2 0.0312(6) 0.0252(6) 0.0253(6) -0.0039(5) -0.0089(5) 0.0148(5) O3 0.0250(6) 0.0256(6) 0.0229(6) 0.0017(5) -0.0048(5) 0.0069(5) O4 0.0239(6) 0.0294(6) 0.0255(6) -0.0005(5) -0.0061(5) 0.0089(5) Cu1 0.02268(12) 0.02365(12) 0.02119(12) -0.00167(8) -0.00468(8) 0.01085(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.532(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.528(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.546(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.531(2) . ? C5 O1 1.272(2) . ? C5 C6 1.401(2) . ? C6 C7 1.404(2) . ? C6 H6 0.9500 . ? C7 O2 1.273(2) . ? C7 C8 1.502(2) . ? C8 C9 1.395(2) . ? C8 C13 1.401(3) . ? C9 C10 1.398(2) . ? C9 H9 0.9500 . ? C10 C11 1.396(3) . ? C10 C14 1.503(2) . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O3 1.274(2) . ? C14 C15 1.405(2) . ? C15 C16 1.396(2) . ? C15 H15 0.9500 . ? C16 O4 1.272(2) . ? C16 C17 1.539(2) . ? C17 C19 1.527(3) . ? C17 C20 1.531(3) . ? C17 C18 1.536(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N1 1.519(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N1 1.459(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N1 1.466(4) . ? C23 C24 1.504(11) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N2 1.364(10) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N2 1.755(6) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N2 1.414(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N2A C24A 1.369(11) . ? N2A C25A 1.474(7) . ? N2A C26A 1.665(6) . ? C21A N1 1.438(4) . ? C21A H21D 0.9800 . ? C21A H21E 0.9800 . ? C21A H21F 0.9800 . ? C22A N1 1.440(5) . ? C22A H22D 0.9800 . ? C22A H22E 0.9800 . ? C22A H22F 0.9800 . ? C23A C24A 1.444(11) . ? C23A N1 1.493(4) . ? C23A H23C 0.9900 . ? C23A H23D 0.9900 . ? C24A H24C 0.9900 . ? C24A H24D 0.9900 . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C26A H26D 0.9800 . ? C26A H26E 0.9800 . ? C26A H26F 0.9800 . ? N1 Cu1 2.4237(15) . ? O1 Cu1 1.9279(13) . ? O2 Cu1 1.9338(12) . ? O3 Cu1 1.9294(13) 2 ? O4 Cu1 1.9302(12) 2 ? Cu1 O3 1.9294(13) 2 ? Cu1 O4 1.9302(13) 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 C5 113.98(16) . . ? C2 C4 C1 109.37(19) . . ? C5 C4 C1 108.17(18) . . ? C2 C4 C3 108.27(19) . . ? C5 C4 C3 106.77(17) . . ? C1 C4 C3 110.3(2) . . ? O1 C5 C6 124.92(16) . . ? O1 C5 C4 114.20(15) . . ? C6 C5 C4 120.85(16) . . ? C5 C6 C7 123.70(17) . . ? C5 C6 H6 118.1 . . ? C7 C6 H6 118.1 . . ? O2 C7 C6 124.72(16) . . ? O2 C7 C8 115.13(15) . . ? C6 C7 C8 120.12(15) . . ? C9 C8 C13 118.50(16) . . ? C9 C8 C7 118.20(15) . . ? C13 C8 C7 123.27(16) . . ? C8 C9 C10 121.67(17) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 118.64(17) . . ? C11 C10 C14 123.22(16) . . ? C9 C10 C14 118.12(16) . . ? C12 C11 C10 120.20(17) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.71(19) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C8 120.26(18) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O3 C14 C15 124.97(17) . . ? O3 C14 C10 114.92(15) . . ? C15 C14 C10 120.11(16) . . ? C16 C15 C14 123.46(17) . . ? C16 C15 H15 118.3 . . ? C14 C15 H15 118.3 . . ? O4 C16 C15 125.13(16) . . ? O4 C16 C17 113.74(15) . . ? C15 C16 C17 121.11(16) . . ? C19 C17 C20 110.01(17) . . ? C19 C17 C18 108.74(18) . . ? C20 C17 C18 109.33(18) . . ? C19 C17 C16 113.78(16) . . ? C20 C17 C16 107.60(16) . . ? C18 C17 C16 107.29(15) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N1 C21 H21A 109.5 . . ? N1 C21 H21B 109.5 . . ? N1 C21 H21C 109.5 . . ? N1 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? N1 C22 H22C 109.5 . . ? N1 C23 C24 114.6(5) . . ? N1 C23 H23A 108.6 . . ? C24 C23 H23A 108.6 . . ? N1 C23 H23B 108.6 . . ? C24 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? N2 C24 C23 115.1(7) . . ? N2 C24 H24A 108.5 . . ? C23 C24 H24A 108.5 . . ? N2 C24 H24B 108.5 . . ? C23 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? C24 N2 C26 120.5(5) . . ? C24 N2 C25 99.9(5) . . ? C26 N2 C25 102.5(3) . . ? C24A N2A C25A 113.5(6) . . ? C24A N2A C26A 102.5(5) . . ? C25A N2A C26A 100.8(4) . . ? N1 C21A H21D 109.5 . . ? N1 C21A H21E 109.5 . . ? H21D C21A H21E 109.5 . . ? N1 C21A H21F 109.5 . . ? H21D C21A H21F 109.5 . . ? H21E C21A H21F 109.5 . . ? N1 C22A H22D 109.5 . . ? N1 C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? N1 C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? C24A C23A N1 116.9(4) . . ? C24A C23A H23C 108.1 . . ? N1 C23A H23C 108.1 . . ? C24A C23A H23D 108.1 . . ? N1 C23A H23D 108.1 . . ? H23C C23A H23D 107.3 . . ? N2A C24A C23A 123.9(6) . . ? N2A C24A H24C 106.3 . . ? C23A C24A H24C 106.3 . . ? N2A C24A H24D 106.3 . . ? C23A C24A H24D 106.3 . . ? H24C C24A H24D 106.4 . . ? N2A C25A H25D 109.5 . . ? N2A C25A H25E 109.5 . . ? H25D C25A H25E 109.5 . . ? N2A C25A H25F 109.5 . . ? H25D C25A H25F 109.5 . . ? H25E C25A H25F 109.5 . . ? N2A C26A H26D 109.5 . . ? N2A C26A H26E 109.5 . . ? H26D C26A H26E 109.5 . . ? N2A C26A H26F 109.5 . . ? H26D C26A H26F 109.5 . . ? H26E C26A H26F 109.5 . . ? C21A N1 C22A 111.2(3) . . ? C21A N1 C22 45.4(3) . . ? C22A N1 C22 144.1(3) . . ? C21A N1 C23 136.6(3) . . ? C22A N1 C23 63.3(2) . . ? C22 N1 C23 112.0(3) . . ? C21A N1 C23A 109.0(3) . . ? C22A N1 C23A 111.2(3) . . ? C22 N1 C23A 67.2(2) . . ? C23 N1 C23A 49.1(2) . . ? C21A N1 C21 62.9(2) . . ? C22A N1 C21 49.9(2) . . ? C22 N1 C21 106.1(3) . . ? C23 N1 C21 107.0(3) . . ? C23A N1 C21 139.0(3) . . ? C21A N1 Cu1 105.77(18) . . ? C22A N1 Cu1 106.12(18) . . ? C22 N1 Cu1 106.82(18) . . ? C23 N1 Cu1 117.21(19) . . ? C23A N1 Cu1 113.50(19) . . ? C21 N1 Cu1 107.15(17) . . ? C5 O1 Cu1 127.11(11) . . ? C7 O2 Cu1 127.11(11) . . ? C14 O3 Cu1 127.15(11) . 2 ? C16 O4 Cu1 127.15(11) . 2 ? O1 Cu1 O3 172.90(5) . 2 ? O1 Cu1 O4 86.91(6) . 2 ? O3 Cu1 O4 91.77(5) 2 2 ? O1 Cu1 O2 91.75(6) . . ? O3 Cu1 O2 87.78(5) 2 . ? O4 Cu1 O2 165.58(6) 2 . ? O1 Cu1 N1 94.56(5) . . ? O3 Cu1 N1 92.53(5) 2 . ? O4 Cu1 N1 96.88(5) 2 . ? O2 Cu1 N1 97.54(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C4 C5 O1 -175.60(19) . . . . ? C1 C4 C5 O1 -53.7(2) . . . . ? C3 C4 C5 O1 64.9(2) . . . . ? C2 C4 C5 C6 6.5(3) . . . . ? C1 C4 C5 C6 128.4(2) . . . . ? C3 C4 C5 C6 -112.9(2) . . . . ? O1 C5 C6 C7 -3.4(3) . . . . ? C4 C5 C6 C7 174.19(18) . . . . ? C5 C6 C7 O2 5.7(3) . . . . ? C5 C6 C7 C8 -172.56(17) . . . . ? O2 C7 C8 C9 6.5(2) . . . . ? C6 C7 C8 C9 -175.15(17) . . . . ? O2 C7 C8 C13 -171.78(18) . . . . ? C6 C7 C8 C13 6.6(3) . . . . ? C13 C8 C9 C10 1.5(3) . . . . ? C7 C8 C9 C10 -176.85(16) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C8 C9 C10 C14 -179.07(16) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C14 C10 C11 C12 177.85(19) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C11 C12 C13 C8 0.1(3) . . . . ? C9 C8 C13 C12 -1.2(3) . . . . ? C7 C8 C13 C12 177.02(19) . . . . ? C11 C10 C14 O3 -165.21(18) . . . . ? C9 C10 C14 O3 13.2(2) . . . . ? C11 C10 C14 C15 14.2(3) . . . . ? C9 C10 C14 C15 -167.46(17) . . . . ? O3 C14 C15 C16 5.0(3) . . . . ? C10 C14 C15 C16 -174.29(17) . . . . ? C14 C15 C16 O4 -0.3(3) . . . . ? C14 C15 C16 C17 178.25(17) . . . . ? O4 C16 C17 C19 178.07(16) . . . . ? C15 C16 C17 C19 -0.6(3) . . . . ? O4 C16 C17 C20 -59.8(2) . . . . ? C15 C16 C17 C20 121.6(2) . . . . ? O4 C16 C17 C18 57.8(2) . . . . ? C15 C16 C17 C18 -120.9(2) . . . . ? N1 C23 C24 N2 -179.4(4) . . . . ? C23 C24 N2 C26 70.4(7) . . . . ? C23 C24 N2 C25 -178.6(5) . . . . ? C25A N2A C24A C23A -67.6(9) . . . . ? C26A N2A C24A C23A -175.4(7) . . . . ? N1 C23A C24A N2A 176.9(6) . . . . ? C24 C23 N1 C21A 122.2(5) . . . . ? C24 C23 N1 C22A -144.6(5) . . . . ? C24 C23 N1 C22 74.6(5) . . . . ? C24 C23 N1 C23A 49.1(4) . . . . ? C24 C23 N1 C21 -169.6(4) . . . . ? C24 C23 N1 Cu1 -49.4(5) . . . . ? C24A C23A N1 C21A 173.6(5) . . . . ? C24A C23A N1 C22A -63.5(6) . . . . ? C24A C23A N1 C22 155.3(6) . . . . ? C24A C23A N1 C23 -50.4(5) . . . . ? C24A C23A N1 C21 -116.2(6) . . . . ? C24A C23A N1 Cu1 56.1(5) . . . . ? C6 C5 O1 Cu1 -5.0(3) . . . . ? C4 C5 O1 Cu1 177.24(13) . . . . ? C6 C7 O2 Cu1 0.8(3) . . . . ? C8 C7 O2 Cu1 179.09(11) . . . . ? C15 C14 O3 Cu1 -3.3(3) . . . 2 ? C10 C14 O3 Cu1 176.01(11) . . . 2 ? C15 C16 O4 Cu1 -5.6(3) . . . 2 ? C17 C16 O4 Cu1 175.81(11) . . . 2 ? C5 O1 Cu1 O4 -157.38(16) . . . 2 ? C5 O1 Cu1 O2 8.25(16) . . . . ? C5 O1 Cu1 N1 105.95(15) . . . . ? C7 O2 Cu1 O1 -6.18(15) . . . . ? C7 O2 Cu1 O3 166.73(15) . . . 2 ? C7 O2 Cu1 O4 78.2(3) . . . 2 ? C7 O2 Cu1 N1 -101.02(15) . . . . ? C21A N1 Cu1 O1 79.0(2) . . . . ? C22A N1 Cu1 O1 -39.1(2) . . . . ? C22 N1 Cu1 O1 126.5(2) . . . . ? C23 N1 Cu1 O1 -107.0(2) . . . . ? C23A N1 Cu1 O1 -161.5(2) . . . . ? C21 N1 Cu1 O1 13.15(19) . . . . ? C21A N1 Cu1 O3 -100.5(2) . . . 2 ? C22A N1 Cu1 O3 141.3(2) . . . 2 ? C22 N1 Cu1 O3 -53.1(2) . . . 2 ? C23 N1 Cu1 O3 73.5(2) . . . 2 ? C23A N1 Cu1 O3 18.9(2) . . . 2 ? C21 N1 Cu1 O3 -166.38(19) . . . 2 ? C21A N1 Cu1 O4 -8.4(2) . . . 2 ? C22A N1 Cu1 O4 -126.6(2) . . . 2 ? C22 N1 Cu1 O4 39.0(2) . . . 2 ? C23 N1 Cu1 O4 165.6(2) . . . 2 ? C23A N1 Cu1 O4 111.0(2) . . . 2 ? C21 N1 Cu1 O4 -74.28(19) . . . 2 ? C21A N1 Cu1 O2 171.4(2) . . . . ? C22A N1 Cu1 O2 53.2(2) . . . . ? C22 N1 Cu1 O2 -141.2(2) . . . . ? C23 N1 Cu1 O2 -14.6(2) . . . . ? C23A N1 Cu1 O2 -69.2(2) . . . . ? C21 N1 Cu1 O2 105.53(19) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.782 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.064 # Attachment 'Fig_Cu_mmorph_at_RT.CIF' data_lj303sad _database_code_depnum_ccdc_archive 'CCDC 754712' #TrackingRef 'Fig_Cu_mmorph_at_RT.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H70 Cu2 N2 O10' _chemical_formula_sum 'C50 H70 Cu2 N2 O10' _chemical_formula_weight 986.16 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 triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' #_intl_tables_symmetry_no. '2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.108(4) _cell_length_b 11.354(6) _cell_length_c 16.593(9) _cell_angle_alpha 82.904(8) _cell_angle_beta 84.495(8) _cell_angle_gamma 72.746(8) _cell_volume 1266.5(11) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1150 _cell_measurement_theta_min 2.352 _cell_measurement_theta_max 21.502 _exptl_crystal_description blade _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.736 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 293(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8318 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.1282 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 28.37 _reflns_number_total 5499 _reflns_number_gt 2804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution "'SIR97 (Altomare, et. al. 1999)'" _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _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^)+(0.0745P)^2^+0.4612P] 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 5499 _refine_ls_number_parameters 296 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1650 _refine_ls_R_factor_gt 0.0723 _refine_ls_wR_factor_ref 0.1884 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _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 C1A C 0.1837(17) 0.3780(12) 0.4765(7) 0.110(2) Uani 0.35 1 d PD A 1 H1A1 H 0.0520 0.3866 0.4625 0.166 Uiso 0.35 1 calc PR A 1 H1A2 H 0.1995 0.4586 0.4789 0.166 Uiso 0.35 1 calc PR A 1 H1A3 H 0.2066 0.3308 0.5286 0.166 Uiso 0.35 1 calc PR A 1 C2A C 0.5301(13) 0.3204(15) 0.4370(9) 0.110(2) Uani 0.35 1 d PD A 1 H2A1 H 0.5571 0.3932 0.4087 0.166 Uiso 0.35 1 calc PR A 1 H2A2 H 0.6343 0.2484 0.4236 0.166 Uiso 0.35 1 calc PR A 1 H2A3 H 0.5220 0.3258 0.4946 0.166 Uiso 0.35 1 calc PR A 1 C3A C 0.346(3) 0.1737(6) 0.4379(9) 0.110(2) Uani 0.35 1 d PD A 1 H3A1 H 0.3646 0.1561 0.4952 0.166 Uiso 0.35 1 calc PR A 1 H3A2 H 0.4563 0.1218 0.4084 0.166 Uiso 0.35 1 calc PR A 1 H3A3 H 0.2269 0.1578 0.4264 0.166 Uiso 0.35 1 calc PR A 1 C1 C 0.114(2) 0.3131(11) 0.4399(5) 0.110(2) Uani 0.65 1 d P A 2 H1A H 0.1054 0.2897 0.4975 0.166 Uiso 0.65 1 calc PR A 2 H1B H 0.0758 0.2559 0.4117 0.166 Uiso 0.65 1 calc PR A 2 H1C H 0.0282 0.3952 0.4279 0.166 Uiso 0.65 1 calc PR A 2 C2 C 0.374(2) 0.4042(11) 0.4595(5) 0.110(2) Uani 0.65 1 d P A 2 H2A H 0.2754 0.4823 0.4506 0.166 Uiso 0.65 1 calc PR A 2 H2B H 0.5019 0.4140 0.4419 0.166 Uiso 0.65 1 calc PR A 2 H2C H 0.3720 0.3756 0.5164 0.166 Uiso 0.65 1 calc PR A 2 C3 C 0.463(2) 0.1831(11) 0.4329(6) 0.110(2) Uani 0.65 1 d P A 2 H3A H 0.4460 0.1602 0.4902 0.166 Uiso 0.65 1 calc PR A 2 H3B H 0.5987 0.1812 0.4192 0.166 Uiso 0.65 1 calc PR A 2 H3C H 0.4299 0.1259 0.4029 0.166 Uiso 0.65 1 calc PR A 2 C4 C 0.3329(8) 0.3107(5) 0.4117(3) 0.0609(15) Uani 1 1 d D . . C5 C 0.3321(7) 0.3552(5) 0.3235(3) 0.0453(12) Uani 1 1 d . A . C6 C 0.4195(7) 0.2756(5) 0.2642(3) 0.0482(13) Uani 1 1 d . . . H6 H 0.4781 0.1929 0.2818 0.058 Uiso 1 1 calc R A . C7 C 0.4263(7) 0.3101(4) 0.1807(3) 0.0423(11) Uani 1 1 d . A . C8 C 0.5264(6) 0.2149(4) 0.1230(3) 0.0402(11) Uani 1 1 d . . . C9 C 0.5826(6) 0.2548(4) 0.0446(2) 0.0380(11) Uani 1 1 d . A . H9 H 0.5568 0.3394 0.0294 0.046 Uiso 1 1 calc R . . C10 C 0.6766(7) 0.1722(4) -0.0121(3) 0.0424(12) Uani 1 1 d . . . C11 C 0.7145(8) 0.0468(5) 0.0125(3) 0.0590(15) Uani 1 1 d . A . H11 H 0.7796 -0.0107 -0.0236 0.071 Uiso 1 1 calc R . . C12 C 0.6570(9) 0.0066(5) 0.0896(3) 0.0655(16) Uani 1 1 d . . . H12 H 0.6826 -0.0780 0.1049 0.079 Uiso 1 1 calc R A . C13 C 0.5633(8) 0.0883(5) 0.1443(3) 0.0555(14) Uani 1 1 d . A . H13 H 0.5238 0.0592 0.1961 0.067 Uiso 1 1 calc R . . C14 C 0.7277(7) 0.2229(5) -0.0960(3) 0.0433(12) Uani 1 1 d . A . C15 C 0.8033(7) 0.1432(5) -0.1569(3) 0.0521(13) Uani 1 1 d . . . H15 H 0.8202 0.0589 -0.1431 0.063 Uiso 1 1 calc R A . C16 C 0.8541(7) 0.1812(5) -0.2358(3) 0.0481(13) Uani 1 1 d . A . C17 C 0.9260(9) 0.0891(5) -0.3009(3) 0.0596(15) Uani 1 1 d . . . C18 C 1.1235(11) 0.1050(6) -0.3407(4) 0.095(2) Uani 1 1 d . A . H18A H 1.1598 0.0604 -0.3880 0.143 Uiso 1 1 calc R . . H18B H 1.2243 0.0732 -0.3026 0.143 Uiso 1 1 calc R . . H18C H 1.1092 0.1914 -0.3563 0.143 Uiso 1 1 calc R . . C19 C 0.9647(10) -0.0468(5) -0.2673(4) 0.0787(19) Uani 1 1 d . A . H19A H 0.8426 -0.0618 -0.2459 0.118 Uiso 1 1 calc R . . H19B H 1.0546 -0.0654 -0.2248 0.118 Uiso 1 1 calc R . . H19C H 1.0211 -0.0987 -0.3102 0.118 Uiso 1 1 calc R . . C20 C 0.7703(13) 0.1222(7) -0.3627(4) 0.124(3) Uani 1 1 d . A . H20A H 0.6499 0.1096 -0.3370 0.186 Uiso 1 1 calc R . . H20B H 0.8151 0.0706 -0.4064 0.186 Uiso 1 1 calc R . . H20C H 0.7471 0.2076 -0.3838 0.186 Uiso 1 1 calc R . . C21 C -0.2719(12) 0.5920(9) 0.2859(5) 0.111(3) Uani 1 1 d . . . H21A H -0.1524 0.5777 0.3140 0.133 Uiso 1 1 calc R . . H21B H -0.3808 0.6431 0.3174 0.133 Uiso 1 1 calc R . . C22 C -0.2513(9) 0.6558(7) 0.2057(5) 0.091(2) Uani 1 1 d . . . H22A H -0.3739 0.6742 0.1792 0.109 Uiso 1 1 calc R . . H22B H -0.2264 0.7338 0.2113 0.109 Uiso 1 1 calc R . . C23 C -0.1322(10) 0.4637(7) 0.1490(5) 0.092(2) Uani 1 1 d . . . H23A H -0.2514 0.4779 0.1207 0.111 Uiso 1 1 calc R . . H23B H -0.0230 0.4112 0.1184 0.111 Uiso 1 1 calc R . . C24 C -0.1546(11) 0.4038(8) 0.2305(6) 0.105(3) Uani 1 1 d . . . H24A H -0.1804 0.3256 0.2265 0.126 Uiso 1 1 calc R . . H24B H -0.0316 0.3859 0.2567 0.126 Uiso 1 1 calc R . . C25 C -0.0932(12) 0.6423(8) 0.0741(4) 0.116(3) Uani 1 1 d . . . H25A H -0.2129 0.6457 0.0504 0.174 Uiso 1 1 calc R . . H25B H 0.0180 0.5955 0.0426 0.174 Uiso 1 1 calc R . . H25C H -0.0841 0.7249 0.0747 0.174 Uiso 1 1 calc R . . N1 N -0.0939(7) 0.5836(5) 0.1562(3) 0.0757(15) Uani 1 1 d . . . O1 O 0.2431(5) 0.4688(3) 0.30697(18) 0.0512(9) Uani 1 1 d . . . O2 O 0.3578(5) 0.4200(3) 0.14763(17) 0.0500(9) Uani 1 1 d . . . O3 O 0.6950(5) 0.3386(3) -0.10644(18) 0.0500(9) Uani 1 1 d . . . O4 O 0.8440(6) 0.2918(3) -0.26281(19) 0.0612(10) Uani 1 1 d . . . O5 O -0.3074(9) 0.4758(7) 0.2791(4) 0.135(2) Uani 1 1 d . . . Cu1 Cu 0.24367(10) 0.56445(6) 0.20352(4) 0.0519(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.174(7) 0.114(5) 0.039(2) 0.003(3) -0.001(4) -0.042(4) C2A 0.174(7) 0.114(5) 0.039(2) 0.003(3) -0.001(4) -0.042(4) C3A 0.174(7) 0.114(5) 0.039(2) 0.003(3) -0.001(4) -0.042(4) C1 0.174(7) 0.114(5) 0.039(2) 0.003(3) -0.001(4) -0.042(4) C2 0.174(7) 0.114(5) 0.039(2) 0.003(3) -0.001(4) -0.042(4) C3 0.174(7) 0.114(5) 0.039(2) 0.003(3) -0.001(4) -0.042(4) C4 0.085(4) 0.055(4) 0.035(2) -0.006(2) 0.004(3) -0.011(3) C5 0.053(3) 0.050(3) 0.034(2) -0.001(2) -0.002(2) -0.016(2) C6 0.058(3) 0.043(3) 0.041(2) 0.002(2) -0.007(2) -0.012(2) C7 0.043(3) 0.045(3) 0.041(2) -0.001(2) -0.003(2) -0.015(2) C8 0.040(2) 0.038(3) 0.043(2) -0.002(2) -0.005(2) -0.013(2) C9 0.045(3) 0.034(3) 0.035(2) 0.0009(18) -0.0029(19) -0.014(2) C10 0.048(3) 0.040(3) 0.037(2) 0.002(2) -0.007(2) -0.009(2) C11 0.078(4) 0.044(3) 0.046(3) -0.003(2) 0.005(3) -0.008(3) C12 0.100(4) 0.035(3) 0.054(3) 0.000(2) 0.000(3) -0.012(3) C13 0.083(4) 0.042(3) 0.043(3) 0.003(2) 0.005(2) -0.025(3) C14 0.046(3) 0.042(3) 0.040(2) -0.004(2) -0.001(2) -0.009(2) C15 0.069(3) 0.041(3) 0.044(3) -0.006(2) 0.005(2) -0.013(2) C16 0.053(3) 0.044(3) 0.046(3) -0.013(2) 0.000(2) -0.010(2) C17 0.084(4) 0.049(3) 0.046(3) -0.017(2) 0.008(3) -0.018(3) C18 0.127(6) 0.072(5) 0.075(4) -0.022(3) 0.049(4) -0.022(4) C19 0.110(5) 0.047(4) 0.075(4) -0.020(3) 0.019(4) -0.019(3) C20 0.160(8) 0.102(6) 0.095(5) -0.046(5) -0.059(5) 0.016(5) C21 0.092(6) 0.123(8) 0.119(7) -0.037(6) 0.005(5) -0.028(5) C22 0.065(4) 0.089(5) 0.113(6) -0.032(5) -0.013(4) -0.003(4) C23 0.075(5) 0.089(6) 0.118(6) -0.022(5) -0.005(4) -0.029(4) C24 0.070(5) 0.106(6) 0.141(7) -0.010(6) -0.003(5) -0.029(4) C25 0.112(6) 0.151(8) 0.087(5) -0.013(5) -0.038(5) -0.030(5) N1 0.062(3) 0.074(4) 0.081(3) 0.000(3) -0.003(3) -0.008(3) O1 0.065(2) 0.049(2) 0.0359(16) -0.0048(15) 0.0065(15) -0.0129(18) O2 0.067(2) 0.040(2) 0.0363(16) 0.0004(14) 0.0073(15) -0.0090(16) O3 0.071(2) 0.034(2) 0.0393(16) -0.0021(14) 0.0071(15) -0.0110(16) O4 0.091(3) 0.044(2) 0.0427(18) -0.0080(16) 0.0183(17) -0.0160(19) O5 0.098(4) 0.159(6) 0.155(6) -0.011(5) 0.008(4) -0.056(4) Cu1 0.0675(4) 0.0412(4) 0.0402(3) -0.0041(2) 0.0102(3) -0.0097(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 C1A C4 1.5390(12) . ? C1A H1A1 0.9600 . ? C1A H1A2 0.9600 . ? C1A H1A3 0.9600 . ? C2A C4 1.5398(12) . ? C2A H2A1 0.9600 . ? C2A H2A2 0.9600 . ? C2A H2A3 0.9600 . ? C3A C4 1.5394(13) . ? C3A H3A1 0.9600 . ? C3A H3A2 0.9600 . ? C3A H3A3 0.9600 . ? C1 C4 1.572(14) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.510(12) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.491(13) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.488(6) . ? C5 O1 1.265(5) . ? C5 C6 1.392(6) . ? C6 C7 1.394(6) . ? C6 H6 0.9300 . ? C7 O2 1.271(5) . ? C7 C8 1.504(6) . ? C8 C9 1.385(6) . ? C8 C13 1.389(7) . ? C9 C10 1.391(6) . ? C9 H9 0.9300 . ? C10 C11 1.385(7) . ? C10 C14 1.493(6) . ? C11 C12 1.371(7) . ? C11 H11 0.9300 . ? C12 C13 1.360(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O3 1.258(5) . ? C14 C15 1.402(6) . ? C15 C16 1.375(6) . ? C15 H15 0.9300 . ? C16 O4 1.264(6) . ? C16 C17 1.543(6) . ? C17 C20 1.514(8) . ? C17 C19 1.528(8) . ? C17 C18 1.543(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O5 1.434(9) . ? C21 C22 1.450(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N1 1.430(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.453(10) . ? C23 N1 1.486(8) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 O5 1.403(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 N1 1.441(8) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? O1 Cu1 1.915(3) . ? O2 Cu1 1.911(3) . ? O3 Cu1 1.925(3) 2_665 ? O4 Cu1 1.922(3) 2_665 ? Cu1 O4 1.922(3) 2_665 ? Cu1 O3 1.925(3) 2_665 ? N1 Cu1 2.536(5) . ? 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 C4 C1A H1A1 109.5 . . ? C4 C1A H1A2 109.5 . . ? C4 C1A H1A3 109.5 . . ? C4 C2A H2A1 109.5 . . ? C4 C2A H2A2 109.5 . . ? C4 C2A H2A3 109.5 . . ? C4 C3A H3A1 109.5 . . ? C4 C3A H3A2 109.5 . . ? C4 C3A H3A3 109.5 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1A C4 C3A 102.48(9) . . ? C1A C4 C5 123.6(6) . . ? C3A C4 C5 119.0(7) . . ? C1A C4 C3 120.0(7) . . ? C5 C4 C3 115.5(5) . . ? C1A C4 C2 57.5(6) . . ? C3A C4 C2 128.9(7) . . ? C5 C4 C2 110.0(5) . . ? C3 C4 C2 111.7(8) . . ? C1A C4 C1 47.0(7) . . ? C3A C4 C1 76.1(7) . . ? C5 C4 C1 106.2(5) . . ? C3 C4 C1 108.3(8) . . ? C2 C4 C1 104.3(7) . . ? C1A C4 C2A 102.44(10) . . ? C3A C4 C2A 102.42(9) . . ? C5 C4 C2A 103.9(7) . . ? C3 C4 C2A 71.4(8) . . ? C2 C4 C2A 49.9(7) . . ? C1 C4 C2A 146.1(6) . . ? O1 C5 C6 123.2(4) . . ? O1 C5 C4 115.1(4) . . ? C6 C5 C4 121.7(4) . . ? C5 C6 C7 125.2(4) . . ? C5 C6 H6 117.4 . . ? C7 C6 H6 117.4 . . ? O2 C7 C6 124.7(4) . . ? O2 C7 C8 115.3(4) . . ? C6 C7 C8 119.9(4) . . ? C9 C8 C13 118.3(4) . . ? C9 C8 C7 118.8(4) . . ? C13 C8 C7 123.0(4) . . ? C8 C9 C10 122.1(4) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C11 C10 C9 117.6(4) . . ? C11 C10 C14 123.6(4) . . ? C9 C10 C14 118.7(4) . . ? C12 C11 C10 120.6(5) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 121.2(5) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 120.2(4) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O3 C14 C15 124.5(4) . . ? O3 C14 C10 115.3(4) . . ? C15 C14 C10 120.2(4) . . ? C16 C15 C14 124.4(5) . . ? C16 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? O4 C16 C15 125.0(4) . . ? O4 C16 C17 113.5(4) . . ? C15 C16 C17 121.6(5) . . ? C20 C17 C19 109.8(5) . . ? C20 C17 C18 110.9(6) . . ? C19 C17 C18 107.1(5) . . ? C20 C17 C16 107.4(5) . . ? C19 C17 C16 114.2(4) . . ? C18 C17 C16 107.5(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 C21 C22 110.2(7) . . ? O5 C21 H21A 109.6 . . ? C22 C21 H21A 109.6 . . ? O5 C21 H21B 109.6 . . ? C22 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? N1 C22 C21 111.9(6) . . ? N1 C22 H22A 109.2 . . ? C21 C22 H22A 109.2 . . ? N1 C22 H22B 109.2 . . ? C21 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C24 C23 N1 108.3(6) . . ? C24 C23 H23A 110.0 . . ? N1 C23 H23A 110.0 . . ? C24 C23 H23B 110.0 . . ? N1 C23 H23B 110.0 . . ? H23A C23 H23B 108.4 . . ? O5 C24 C23 113.2(7) . . ? O5 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? O5 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 N1 C25 110.5(6) . . ? C22 N1 C23 108.8(6) . . ? C25 N1 C23 104.9(6) . . ? C5 O1 Cu1 127.1(3) . . ? C7 O2 Cu1 126.0(3) . . ? C14 O3 Cu1 127.2(3) . 2_665 ? C16 O4 Cu1 127.2(3) . 2_665 ? C24 O5 C21 109.8(6) . . ? O2 Cu1 O1 92.53(13) . . ? O2 Cu1 O4 174.06(16) . 2_665 ? O1 Cu1 O4 86.44(15) . 2_665 ? O2 Cu1 O3 87.96(14) . 2_665 ? O1 Cu1 O3 166.28(15) . 2_665 ? O4 Cu1 O3 91.65(14) 2_665 2_665 ? O2 Cu1 N1 90.82(16) . . ? O1 Cu1 N1 102.42(16) . . ? O4 Cu1 N1 95.12(17) 2_665 . ? O3 Cu1 N1 91.28(16) 2_665 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A C4 C5 O1 20.6(9) . . . . ? C3A C4 C5 O1 152.2(8) . . . . ? C3 C4 C5 O1 -170.6(7) . . . . ? C2 C4 C5 O1 -43.0(8) . . . . ? C1 C4 C5 O1 69.3(7) . . . . ? C2A C4 C5 O1 -94.9(7) . . . . ? C1A C4 C5 C6 -158.0(8) . . . . ? C3A C4 C5 C6 -26.4(9) . . . . ? C3 C4 C5 C6 10.8(9) . . . . ? C2 C4 C5 C6 138.5(7) . . . . ? C1 C4 C5 C6 -109.2(7) . . . . ? C2A C4 C5 C6 86.6(8) . . . . ? O1 C5 C6 C7 2.1(8) . . . . ? C4 C5 C6 C7 -179.5(5) . . . . ? C5 C6 C7 O2 2.0(8) . . . . ? C5 C6 C7 C8 179.7(5) . . . . ? O2 C7 C8 C9 16.6(6) . . . . ? C6 C7 C8 C9 -161.4(4) . . . . ? O2 C7 C8 C13 -162.6(5) . . . . ? C6 C7 C8 C13 19.4(7) . . . . ? C13 C8 C9 C10 -1.0(7) . . . . ? C7 C8 C9 C10 179.7(4) . . . . ? C8 C9 C10 C11 -0.5(7) . . . . ? C8 C9 C10 C14 178.4(4) . . . . ? C9 C10 C11 C12 1.3(8) . . . . ? C14 C10 C11 C12 -177.5(5) . . . . ? C10 C11 C12 C13 -0.7(9) . . . . ? C11 C12 C13 C8 -0.9(9) . . . . ? C9 C8 C13 C12 1.7(8) . . . . ? C7 C8 C13 C12 -179.1(5) . . . . ? C11 C10 C14 O3 -175.4(5) . . . . ? C9 C10 C14 O3 5.7(6) . . . . ? C11 C10 C14 C15 5.6(7) . . . . ? C9 C10 C14 C15 -173.3(4) . . . . ? O3 C14 C15 C16 1.0(8) . . . . ? C10 C14 C15 C16 179.9(5) . . . . ? C14 C15 C16 O4 1.9(8) . . . . ? C14 C15 C16 C17 -176.6(5) . . . . ? O4 C16 C17 C20 -65.6(7) . . . . ? C15 C16 C17 C20 113.1(6) . . . . ? O4 C16 C17 C19 172.5(5) . . . . ? C15 C16 C17 C19 -8.8(8) . . . . ? O4 C16 C17 C18 53.8(6) . . . . ? C15 C16 C17 C18 -127.5(6) . . . . ? O5 C21 C22 N1 -58.5(9) . . . . ? N1 C23 C24 O5 58.3(8) . . . . ? C21 C22 N1 C25 172.7(7) . . . . ? C21 C22 N1 C23 58.1(8) . . . . ? C24 C23 N1 C22 -56.2(7) . . . . ? C24 C23 N1 C25 -174.5(6) . . . . ? C6 C5 O1 Cu1 -11.4(7) . . . . ? C4 C5 O1 Cu1 170.1(3) . . . . ? C6 C7 O2 Cu1 3.7(7) . . . . ? C8 C7 O2 Cu1 -174.1(3) . . . . ? C15 C14 O3 Cu1 -5.1(7) . . . 2_665 ? C10 C14 O3 Cu1 175.9(3) . . . 2_665 ? C15 C16 O4 Cu1 -0.2(8) . . . 2_665 ? C17 C16 O4 Cu1 178.4(3) . . . 2_665 ? C23 C24 O5 C21 -58.7(9) . . . . ? C22 C21 O5 C24 56.6(9) . . . . ? C7 O2 Cu1 O1 -8.9(4) . . . . ? C7 O2 Cu1 O3 157.4(4) . . . 2_665 ? C5 O1 Cu1 O2 12.9(4) . . . . ? C5 O1 Cu1 O4 -161.2(4) . . . 2_665 ? C5 O1 Cu1 O3 -78.9(7) . . . 2_665 ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.437 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.074 # Attachment 'Figs_8_9.CIF' data_lj163sad _database_code_depnum_ccdc_archive 'CCDC 754713' #TrackingRef 'Figs_8_9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H68 N4 Ni2 O8, C6 H14 N2' _chemical_formula_sum ' C66 H82 N6 Ni2 O8 ' _chemical_formula_weight 1204.76 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 _symmetry_space_group_name_Hall '-p 1' #_symmetry_international_tables_no '2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.206(5) _cell_length_b 11.144(6) _cell_length_c 16.107(8) _cell_angle_alpha 74.619(8) _cell_angle_beta 79.261(9) _cell_angle_gamma 83.014(9) _cell_volume 1560.8(13) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3424 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 20.75 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.852 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 67 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.04 _diffrn_reflns_number 15431 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0620 _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 -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.51 _reflns_number_total 7242 _reflns_number_gt 5031 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _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^)+(0.0494P)^2^+0.2397P] 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 7242 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1600(3) 0.3939(3) 0.7110(2) 0.0577(9) Uani 1 1 d . . . H1A H -0.2312 0.4544 0.7343 0.087 Uiso 1 1 calc R . . H1B H -0.1705 0.3107 0.7504 0.087 Uiso 1 1 calc R . . H1C H -0.1793 0.3930 0.6534 0.087 Uiso 1 1 calc R . . C2 C 0.0294(3) 0.4206(2) 0.79411(16) 0.0427(7) Uani 1 1 d . . . H2A H 0.1312 0.4415 0.7904 0.064 Uiso 1 1 calc R . . H2B H 0.0174 0.3350 0.8295 0.064 Uiso 1 1 calc R . . H2C H -0.0401 0.4785 0.8211 0.064 Uiso 1 1 calc R . . C3 C 0.0120(3) 0.5645(2) 0.64865(18) 0.0527(8) Uani 1 1 d . . . H3A H 0.1142 0.5863 0.6419 0.079 Uiso 1 1 calc R . . H3B H -0.0554 0.6212 0.6780 0.079 Uiso 1 1 calc R . . H3C H -0.0140 0.5723 0.5910 0.079 Uiso 1 1 calc R . . C4 C -0.0020(3) 0.4311(2) 0.70285(16) 0.0324(6) Uani 1 1 d . . . C5 C 0.1025(2) 0.3324(2) 0.66473(15) 0.0276(5) Uani 1 1 d . . . C6 C 0.2017(2) 0.3673(2) 0.58679(15) 0.0295(5) Uani 1 1 d . . . H6 H 0.2061 0.4542 0.5605 0.035 Uiso 1 1 calc R . . C7 C 0.2955(2) 0.2852(2) 0.54400(14) 0.0247(5) Uani 1 1 d . . . C8 C 0.4013(2) 0.3362(2) 0.46194(14) 0.0240(5) Uani 1 1 d . . . C9 C 0.4894(2) 0.2518(2) 0.41973(14) 0.0240(5) Uani 1 1 d . . . H9 H 0.4821 0.1648 0.4443 0.029 Uiso 1 1 calc R . . C10 C 0.5879(2) 0.2917(2) 0.34240(14) 0.0234(5) Uani 1 1 d . . . C11 C 0.5960(2) 0.4195(2) 0.30769(15) 0.0292(5) Uani 1 1 d . . . H11 H 0.6600 0.4488 0.2543 0.035 Uiso 1 1 calc R . . C12 C 0.5130(2) 0.5045(2) 0.34942(15) 0.0319(5) Uani 1 1 d . . . H12 H 0.5223 0.5914 0.3256 0.038 Uiso 1 1 calc R . . C13 C 0.4159(2) 0.4631(2) 0.42611(15) 0.0300(5) Uani 1 1 d . . . H13 H 0.3588 0.5220 0.4545 0.036 Uiso 1 1 calc R . . C14 C 0.6843(2) 0.1949(2) 0.30229(14) 0.0246(5) Uani 1 1 d . . . C15 C 0.7559(2) 0.2305(2) 0.21595(14) 0.0297(5) Uani 1 1 d . . . H15 H 0.7332 0.3133 0.1840 0.036 Uiso 1 1 calc R . . C16 C 0.8584(2) 0.1548(2) 0.17220(14) 0.0266(5) Uani 1 1 d . . . C17 C 0.9263(3) 0.2073(2) 0.07671(15) 0.0299(5) Uani 1 1 d . . . C18 C 0.8240(4) 0.1787(3) 0.02142(17) 0.0561(8) Uani 1 1 d . . . H18A H 0.8183 0.0882 0.0342 0.084 Uiso 1 1 calc R . . H18B H 0.8630 0.2106 -0.0405 0.084 Uiso 1 1 calc R . . H18C H 0.7247 0.2188 0.0350 0.084 Uiso 1 1 calc R . . C19 C 1.0798(3) 0.1419(3) 0.05787(19) 0.0606(9) Uani 1 1 d . . . H19A H 1.1449 0.1596 0.0941 0.091 Uiso 1 1 calc R . . H19B H 1.1211 0.1724 -0.0039 0.091 Uiso 1 1 calc R . . H19C H 1.0718 0.0517 0.0712 0.091 Uiso 1 1 calc R . . C20 C 0.9409(3) 0.3479(2) 0.05327(17) 0.0439(7) Uani 1 1 d . . . H20A H 0.8419 0.3920 0.0559 0.066 Uiso 1 1 calc R . . H20B H 0.9963 0.3739 -0.0059 0.066 Uiso 1 1 calc R . . H20C H 0.9937 0.3681 0.0947 0.066 Uiso 1 1 calc R . . C21 C -0.0488(3) -0.0654(2) 0.64436(17) 0.0356(6) Uani 1 1 d . . . H21 H -0.0077 -0.1347 0.6838 0.043 Uiso 1 1 calc R . . C22 C -0.1653(3) -0.0824(2) 0.60755(18) 0.0391(6) Uani 1 1 d . . . H22 H -0.2042 -0.1618 0.6220 0.047 Uiso 1 1 calc R . . C23 C -0.2252(3) 0.0162(3) 0.54970(16) 0.0379(6) Uani 1 1 d . . . H23 H -0.3037 0.0061 0.5220 0.045 Uiso 1 1 calc R . . C24 C -0.1681(3) 0.1302(3) 0.53298(17) 0.0398(6) Uani 1 1 d . . . H24 H -0.2088 0.2011 0.4946 0.048 Uiso 1 1 calc R . . C25 C -0.0515(3) 0.1407(2) 0.57241(16) 0.0353(6) Uani 1 1 d . . . H25 H -0.0128 0.2199 0.5601 0.042 Uiso 1 1 calc R . . C26 C 0.3272(3) 0.1166(3) 0.82476(17) 0.0419(7) Uani 1 1 d . . . H26 H 0.2250 0.1292 0.8472 0.050 Uiso 1 1 calc R . . C27 C 0.4296(3) 0.1283(3) 0.8732(2) 0.0558(8) Uani 1 1 d . . . H27 H 0.3990 0.1457 0.9287 0.067 Uiso 1 1 calc R . . C28 C 0.5781(3) 0.1142(3) 0.8398(2) 0.0576(9) Uani 1 1 d . . . H28 H 0.6521 0.1238 0.8710 0.069 Uiso 1 1 calc R . . C29 C 0.6159(3) 0.0862(3) 0.7609(2) 0.0580(9) Uani 1 1 d . . . H29 H 0.7173 0.0748 0.7366 0.070 Uiso 1 1 calc R . . C30 C 0.5070(3) 0.0748(3) 0.71675(18) 0.0464(7) Uani 1 1 d . . . H30 H 0.5354 0.0561 0.6615 0.056 Uiso 1 1 calc R . . C31 C 0.5518(4) 0.4712(3) -0.0802(2) 0.0605(9) Uani 1 1 d . . . H31A H 0.6579 0.4468 -0.0763 0.073 Uiso 1 1 calc R . . H31B H 0.5335 0.4621 -0.1368 0.073 Uiso 1 1 calc R . . C32 C 0.4586(4) 0.3876(3) -0.0078(2) 0.0607(9) Uani 1 1 d . . . H32A H 0.3528 0.4090 -0.0135 0.073 Uiso 1 1 calc R . . H32B H 0.4837 0.3000 -0.0114 0.073 Uiso 1 1 calc R . . C33 C 0.3933(4) 0.3171(4) 0.1473(3) 0.0853(12) Uani 1 1 d . . . H33A H 0.2879 0.3391 0.1437 0.128 Uiso 1 1 calc R . . H33B H 0.4133 0.3260 0.2029 0.128 Uiso 1 1 calc R . . H33C H 0.4188 0.2306 0.1435 0.128 Uiso 1 1 calc R . . N1 N 0.0095(2) 0.04481(18) 0.62708(12) 0.0299(4) Uani 1 1 d . . . N2 N 0.3631(2) 0.08849(18) 0.74763(12) 0.0317(5) Uani 1 1 d . . . N3 N 0.4819(3) 0.3996(3) 0.07587(17) 0.0543(7) Uani 1 1 d . . . O2 O 0.69395(16) 0.08665(14) 0.35237(9) 0.0272(4) Uani 1 1 d . . . O3 O 0.29863(17) 0.16733(14) 0.56877(10) 0.0296(4) Uani 1 1 d . . . O4 O 0.89922(17) 0.04219(14) 0.20450(10) 0.0290(4) Uani 1 1 d . . . O5 O 0.08681(17) 0.22160(14) 0.70959(10) 0.0311(4) Uani 1 1 d . . . Ni1 Ni 0.19364(3) 0.06521(3) 0.681368(19) 0.02692(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0261(14) 0.074(2) 0.077(2) -0.0380(19) 0.0000(14) 0.0098(14) C2 0.0525(16) 0.0408(15) 0.0333(15) -0.0161(12) 0.0073(12) -0.0044(12) C3 0.068(2) 0.0354(15) 0.0406(16) -0.0068(13) 0.0095(14) 0.0174(14) C4 0.0324(13) 0.0306(13) 0.0297(13) -0.0099(11) 0.0046(10) 0.0048(10) C5 0.0260(11) 0.0315(13) 0.0243(12) -0.0084(11) -0.0021(9) 0.0020(10) C6 0.0322(12) 0.0264(13) 0.0258(12) -0.0065(10) 0.0034(10) 0.0006(10) C7 0.0246(11) 0.0290(13) 0.0196(11) -0.0061(10) -0.0013(9) -0.0020(9) C8 0.0221(11) 0.0284(12) 0.0209(11) -0.0063(9) -0.0011(9) -0.0020(9) C9 0.0249(11) 0.0242(12) 0.0217(11) -0.0045(9) -0.0029(9) -0.0017(9) C10 0.0204(10) 0.0286(12) 0.0199(11) -0.0064(9) -0.0007(9) -0.0001(9) C11 0.0267(11) 0.0319(13) 0.0235(12) -0.0029(10) 0.0057(9) -0.0052(10) C12 0.0326(13) 0.0251(13) 0.0323(13) -0.0033(10) 0.0038(10) -0.0029(10) C13 0.0297(12) 0.0285(13) 0.0296(13) -0.0094(10) 0.0022(10) 0.0010(10) C14 0.0214(11) 0.0280(13) 0.0233(12) -0.0058(10) -0.0019(9) -0.0016(9) C15 0.0329(12) 0.0274(13) 0.0207(12) 0.0003(10) 0.0035(10) 0.0028(10) C16 0.0230(11) 0.0340(14) 0.0216(12) -0.0067(10) 0.0003(9) -0.0042(10) C17 0.0356(13) 0.0288(13) 0.0205(12) -0.0049(10) 0.0056(10) -0.0021(10) C18 0.084(2) 0.060(2) 0.0247(14) -0.0028(14) -0.0070(14) -0.0272(17) C19 0.0533(18) 0.061(2) 0.0406(17) 0.0033(15) 0.0259(14) 0.0105(15) C20 0.0609(18) 0.0356(15) 0.0272(14) -0.0052(12) 0.0145(12) -0.0122(13) C21 0.0327(13) 0.0342(14) 0.0390(15) -0.0111(12) -0.0042(11) 0.0029(11) C22 0.0336(13) 0.0375(15) 0.0481(17) -0.0175(13) -0.0029(12) -0.0009(11) C23 0.0277(12) 0.0553(17) 0.0330(14) -0.0207(13) 0.0018(11) -0.0010(12) C24 0.0351(14) 0.0477(17) 0.0312(14) -0.0025(12) -0.0037(11) -0.0008(12) C25 0.0350(13) 0.0386(15) 0.0287(13) -0.0027(11) -0.0023(11) -0.0060(11) C26 0.0329(14) 0.0579(18) 0.0375(15) -0.0235(13) 0.0079(12) -0.0089(12) C27 0.0443(16) 0.087(2) 0.0466(18) -0.0394(17) 0.0066(14) -0.0146(15) C28 0.0406(16) 0.086(2) 0.057(2) -0.0355(18) -0.0036(14) -0.0158(16) C29 0.0276(14) 0.096(3) 0.059(2) -0.0421(19) 0.0058(13) -0.0077(15) C30 0.0312(14) 0.068(2) 0.0435(16) -0.0296(15) 0.0083(12) -0.0030(13) C31 0.0506(18) 0.088(3) 0.0502(19) -0.0339(19) -0.0171(15) 0.0168(17) C32 0.0544(19) 0.063(2) 0.076(2) -0.0339(19) -0.0246(18) 0.0096(16) C33 0.054(2) 0.115(3) 0.080(3) -0.001(2) -0.022(2) -0.014(2) N1 0.0275(10) 0.0331(11) 0.0256(10) -0.0085(9) 0.0045(8) 0.0001(8) N2 0.0308(10) 0.0343(12) 0.0270(11) -0.0100(9) 0.0057(8) -0.0012(9) N3 0.0440(14) 0.0661(18) 0.0529(16) -0.0096(14) -0.0182(12) -0.0005(13) O2 0.0294(8) 0.0263(9) 0.0206(8) -0.0037(7) 0.0042(7) 0.0010(7) O3 0.0311(8) 0.0273(9) 0.0250(8) -0.0057(7) 0.0065(7) -0.0001(7) O4 0.0286(8) 0.0291(9) 0.0241(8) -0.0053(7) 0.0045(7) 0.0011(7) O5 0.0325(9) 0.0288(9) 0.0256(9) -0.0049(7) 0.0069(7) 0.0007(7) Ni1 0.02595(16) 0.02728(17) 0.02262(16) -0.00471(12) 0.00488(11) -0.00007(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.534(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.522(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.518(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.547(3) . ? C5 O5 1.265(3) . ? C5 C6 1.401(3) . ? C6 C7 1.407(3) . ? C6 H6 0.9500 . ? C7 O3 1.266(3) . ? C7 C8 1.509(3) . ? C8 C13 1.391(3) . ? C8 C9 1.398(3) . ? C9 C10 1.398(3) . ? C9 H9 0.9500 . ? C10 C11 1.391(3) . ? C10 C14 1.513(3) . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O2 1.264(3) . ? C14 C15 1.398(3) . ? C15 C16 1.404(3) . ? C15 H15 0.9500 . ? C16 O4 1.264(3) . ? C16 C17 1.534(3) . ? C17 C18 1.523(4) . ? C17 C19 1.525(3) . ? C17 C20 1.528(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N1 1.340(3) . ? C21 C22 1.373(3) . ? C21 H21 0.9500 . ? C22 C23 1.371(4) . ? C22 H22 0.9500 . ? C23 C24 1.375(4) . ? C23 H23 0.9500 . ? C24 C25 1.376(3) . ? C24 H24 0.9500 . ? C25 N1 1.331(3) . ? C25 H25 0.9500 . ? C26 N2 1.334(3) . ? C26 C27 1.368(4) . ? C26 H26 0.9500 . ? C27 C28 1.379(4) . ? C27 H27 0.9500 . ? C28 C29 1.361(4) . ? C28 H28 0.9500 . ? C29 C30 1.368(4) . ? C29 H29 0.9500 . ? C30 N2 1.331(3) . ? C30 H30 0.9500 . ? C31 N3 1.453(4) 2_665 ? C31 C32 1.486(5) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 N3 1.445(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N3 1.451(4) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? N1 Ni1 2.108(2) . ? N2 Ni1 2.123(2) . ? N3 C31 1.453(4) 2_665 ? O2 Ni1 2.0205(17) 2_656 ? O3 Ni1 2.0094(17) . ? O4 Ni1 2.0097(16) 2_656 ? O5 Ni1 2.0120(17) . ? Ni1 O4 2.0097(17) 2_656 ? Ni1 O2 2.0205(17) 2_656 ? 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 C4 C2 109.6(2) . . ? C3 C4 C1 110.1(2) . . ? C2 C4 C1 108.2(2) . . ? C3 C4 C5 114.6(2) . . ? C2 C4 C5 108.0(2) . . ? C1 C4 C5 106.1(2) . . ? O5 C5 C6 125.2(2) . . ? O5 C5 C4 113.72(19) . . ? C6 C5 C4 121.1(2) . . ? C5 C6 C7 125.7(2) . . ? C5 C6 H6 117.1 . . ? C7 C6 H6 117.1 . . ? O3 C7 C6 124.8(2) . . ? O3 C7 C8 115.22(19) . . ? C6 C7 C8 120.0(2) . . ? C13 C8 C9 118.2(2) . . ? C13 C8 C7 123.37(19) . . ? C9 C8 C7 118.4(2) . . ? C8 C9 C10 121.9(2) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 117.89(19) . . ? C11 C10 C14 123.11(19) . . ? C9 C10 C14 118.96(19) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.7(2) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? O2 C14 C15 125.5(2) . . ? O2 C14 C10 115.22(19) . . ? C15 C14 C10 119.2(2) . . ? C14 C15 C16 125.9(2) . . ? C14 C15 H15 117.0 . . ? C16 C15 H15 117.0 . . ? O4 C16 C15 125.2(2) . . ? O4 C16 C17 115.10(19) . . ? C15 C16 C17 119.7(2) . . ? C18 C17 C19 109.7(2) . . ? C18 C17 C20 109.3(2) . . ? C19 C17 C20 108.5(2) . . ? C18 C17 C16 106.45(19) . . ? C19 C17 C16 109.5(2) . . ? C20 C17 C16 113.37(19) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N1 C21 C22 122.9(2) . . ? N1 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? C23 C22 C21 119.4(2) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 118.1(2) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? C23 C24 C25 119.4(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? N1 C25 C24 122.9(2) . . ? N1 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? N2 C26 C27 123.5(2) . . ? N2 C26 H26 118.3 . . ? C27 C26 H26 118.3 . . ? C26 C27 C28 118.7(3) . . ? C26 C27 H27 120.7 . . ? C28 C27 H27 120.7 . . ? C29 C28 C27 118.3(3) . . ? C29 C28 H28 120.9 . . ? C27 C28 H28 120.9 . . ? C28 C29 C30 119.6(3) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? N2 C30 C29 123.1(2) . . ? N2 C30 H30 118.5 . . ? C29 C30 H30 118.5 . . ? N3 C31 C32 110.6(3) 2_665 . ? N3 C31 H31A 109.5 2_665 . ? C32 C31 H31A 109.5 . . ? N3 C31 H31B 109.5 2_665 . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? N3 C32 C31 110.8(3) . . ? N3 C32 H32A 109.5 . . ? C31 C32 H32A 109.5 . . ? N3 C32 H32B 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? N3 C33 H33A 109.5 . . ? N3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C25 N1 C21 117.2(2) . . ? C25 N1 Ni1 121.11(16) . . ? C21 N1 Ni1 121.63(17) . . ? C30 N2 C26 116.9(2) . . ? C30 N2 Ni1 123.27(18) . . ? C26 N2 Ni1 119.85(16) . . ? C32 N3 C33 111.5(3) . . ? C32 N3 C31 109.3(2) . 2_665 ? C33 N3 C31 110.9(3) . 2_665 ? C14 O2 Ni1 125.50(14) . 2_656 ? C7 O3 Ni1 126.88(14) . . ? C16 O4 Ni1 125.68(14) . 2_656 ? C5 O5 Ni1 126.80(14) . . ? O3 Ni1 O4 176.48(6) . 2_656 ? O3 Ni1 O5 90.14(7) . . ? O4 Ni1 O5 92.14(7) 2_656 . ? O3 Ni1 O2 87.08(7) . 2_656 ? O4 Ni1 O2 90.63(7) 2_656 2_656 ? O5 Ni1 O2 177.22(6) . 2_656 ? O3 Ni1 N1 94.23(8) . . ? O4 Ni1 N1 88.52(8) 2_656 . ? O5 Ni1 N1 88.29(7) . . ? O2 Ni1 N1 91.96(7) 2_656 . ? O3 Ni1 N2 90.32(8) . . ? O4 Ni1 N2 87.10(8) 2_656 . ? O5 Ni1 N2 87.80(7) . . ? O2 Ni1 N2 92.16(7) 2_656 . ? N1 Ni1 N2 174.01(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C4 C5 O5 -178.4(2) . . . . ? C2 C4 C5 O5 59.2(3) . . . . ? C1 C4 C5 O5 -56.7(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C2 C4 C5 C6 -121.7(2) . . . . ? C1 C4 C5 C6 122.4(3) . . . . ? O5 C5 C6 C7 2.7(4) . . . . ? C4 C5 C6 C7 -176.3(2) . . . . ? C5 C6 C7 O3 2.8(4) . . . . ? C5 C6 C7 C8 -177.7(2) . . . . ? O3 C7 C8 C13 -178.4(2) . . . . ? C6 C7 C8 C13 2.1(3) . . . . ? O3 C7 C8 C9 1.5(3) . . . . ? C6 C7 C8 C9 -178.0(2) . . . . ? C13 C8 C9 C10 -1.5(3) . . . . ? C7 C8 C9 C10 178.6(2) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 C14 177.6(2) . . . . ? C9 C10 C11 C12 1.9(3) . . . . ? C14 C10 C11 C12 -175.8(2) . . . . ? C10 C11 C12 C13 -1.9(4) . . . . ? C11 C12 C13 C8 0.2(4) . . . . ? C9 C8 C13 C12 1.5(3) . . . . ? C7 C8 C13 C12 -178.6(2) . . . . ? C11 C10 C14 O2 161.4(2) . . . . ? C9 C10 C14 O2 -16.2(3) . . . . ? C11 C10 C14 C15 -17.6(3) . . . . ? C9 C10 C14 C15 164.8(2) . . . . ? O2 C14 C15 C16 -4.7(4) . . . . ? C10 C14 C15 C16 174.1(2) . . . . ? C14 C15 C16 O4 1.1(4) . . . . ? C14 C15 C16 C17 179.3(2) . . . . ? O4 C16 C17 C18 88.6(2) . . . . ? C15 C16 C17 C18 -89.8(3) . . . . ? O4 C16 C17 C19 -29.9(3) . . . . ? C15 C16 C17 C19 151.7(2) . . . . ? O4 C16 C17 C20 -151.3(2) . . . . ? C15 C16 C17 C20 30.4(3) . . . . ? N1 C21 C22 C23 0.7(4) . . . . ? C21 C22 C23 C24 -2.0(4) . . . . ? C22 C23 C24 C25 1.8(4) . . . . ? C23 C24 C25 N1 -0.3(4) . . . . ? N2 C26 C27 C28 2.1(5) . . . . ? C26 C27 C28 C29 -1.6(5) . . . . ? C27 C28 C29 C30 0.9(5) . . . . ? C28 C29 C30 N2 -0.7(5) . . . . ? N3 C31 C32 N3 -58.6(3) 2_665 . . . ? C24 C25 N1 C21 -1.0(3) . . . . ? C24 C25 N1 Ni1 177.45(18) . . . . ? C22 C21 N1 C25 0.8(3) . . . . ? C22 C21 N1 Ni1 -177.63(18) . . . . ? C29 C30 N2 C26 1.0(4) . . . . ? C29 C30 N2 Ni1 -178.0(2) . . . . ? C27 C26 N2 C30 -1.8(4) . . . . ? C27 C26 N2 Ni1 177.3(2) . . . . ? C31 C32 N3 C33 -179.1(3) . . . . ? C31 C32 N3 C31 57.9(3) . . . 2_665 ? C15 C14 O2 Ni1 -3.6(3) . . . 2_656 ? C10 C14 O2 Ni1 177.50(13) . . . 2_656 ? C6 C7 O3 Ni1 -8.4(3) . . . . ? C8 C7 O3 Ni1 172.06(13) . . . . ? C15 C16 O4 Ni1 10.1(3) . . . 2_656 ? C17 C16 O4 Ni1 -168.13(14) . . . 2_656 ? C6 C5 O5 Ni1 -1.7(3) . . . . ? C4 C5 O5 Ni1 177.35(14) . . . . ? C7 O3 Ni1 O5 7.15(18) . . . . ? C7 O3 Ni1 O2 -172.80(18) . . . 2_656 ? C7 O3 Ni1 N1 95.45(18) . . . . ? C7 O3 Ni1 N2 -80.65(19) . . . . ? C5 O5 Ni1 O3 -2.20(19) . . . . ? C5 O5 Ni1 O4 175.12(19) . . . 2_656 ? C5 O5 Ni1 N1 -96.42(19) . . . . ? C5 O5 Ni1 N2 88.11(19) . . . . ? C25 N1 Ni1 O3 -42.96(18) . . . . ? C21 N1 Ni1 O3 135.44(17) . . . . ? C25 N1 Ni1 O4 139.24(18) . . . 2_656 ? C21 N1 Ni1 O4 -42.36(18) . . . 2_656 ? C25 N1 Ni1 O5 47.05(18) . . . . ? C21 N1 Ni1 O5 -134.55(18) . . . . ? C25 N1 Ni1 O2 -130.18(18) . . . 2_656 ? C21 N1 Ni1 O2 48.22(18) . . . 2_656 ? C30 N2 Ni1 O3 -45.5(2) . . . . ? C26 N2 Ni1 O3 135.5(2) . . . . ? C30 N2 Ni1 O4 132.1(2) . . . 2_656 ? C26 N2 Ni1 O4 -46.9(2) . . . 2_656 ? C30 N2 Ni1 O5 -135.6(2) . . . . ? C26 N2 Ni1 O5 45.37(19) . . . . ? C30 N2 Ni1 O2 41.6(2) . . . 2_656 ? C26 N2 Ni1 O2 -137.41(19) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.536 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.062