# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_20111008c_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H48 Cu2 N8 O12' _chemical_formula_sum 'C60 H48 Cu2 N8 O12' _chemical_formula_weight 1200.14 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' Cu Cu 0.3201 1.2651 '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' _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' _cell_length_a 8.7519(5) _cell_length_b 12.8290(7) _cell_length_c 13.3912(7) _cell_angle_alpha 77.7950(10) _cell_angle_beta 89.4330(10) _cell_angle_gamma 71.0390(10) _cell_volume 1387.00(13) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5304 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.61 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 618 _exptl_absorpt_coefficient_mu 0.838 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8306 _exptl_absorpt_correction_T_max 0.8846 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12148 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5110 _reflns_number_gt 4354 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.1575P)^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 5110 _refine_ls_number_parameters 370 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1992 _refine_ls_wR_factor_gt 0.1611 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.15568(5) 0.92986(3) 0.09192(3) 0.0341(2) Uani 1 1 d . . . O1 O 0.1063(3) 0.8708(2) 0.0385(2) 0.0558(8) Uani 1 1 d . . . O2 O 0.3053(3) 0.9138(2) -0.0418(2) 0.0400(6) Uani 1 1 d . . . O3 O 0.6299(6) 0.3205(3) 0.2295(4) 0.1072(16) Uani 1 1 d . . . O4 O -0.1068(3) 0.7720(2) 0.1768(2) 0.0426(6) Uani 1 1 d . . . O5 O -0.3647(4) 0.8396(2) 0.2055(2) 0.0495(7) Uani 1 1 d . . . O6 O -0.2832(9) 0.3146(5) 0.5282(6) 0.173(3) Uani 1 1 d . . . N1 N -0.0611(4) 0.9751(3) 0.2033(2) 0.0389(7) Uani 1 1 d . . . N2 N 0.1270(4) 0.9776(2) 0.3081(2) 0.0400(7) Uani 1 1 d . . . N3 N 0.3354(4) 1.1241(3) 0.1692(2) 0.0378(7) Uani 1 1 d . . . N4 N 0.2168(4) 1.1181(2) 0.0283(2) 0.0366(6) Uani 1 1 d . . . C1 C 0.2472(4) 0.8461(3) 0.0151(3) 0.0341(7) Uani 1 1 d . . . C2 C 0.3587(4) 0.7273(3) 0.0552(3) 0.0331(7) Uani 1 1 d . . . C3 C 0.2981(5) 0.6492(3) 0.1174(3) 0.0457(9) Uani 1 1 d . . . H3 H 0.1904 0.6711 0.1338 0.055 Uiso 1 1 calc R . . C4 C 0.3988(6) 0.5398(3) 0.1541(3) 0.0524(10) Uani 1 1 d . . . H4 H 0.3586 0.4879 0.1953 0.063 Uiso 1 1 calc R . . C5 C 0.5593(5) 0.5067(3) 0.1303(3) 0.0474(9) Uani 1 1 d . . . C6 C 0.6172(5) 0.5834(3) 0.0691(3) 0.0494(9) Uani 1 1 d . . . H6 H 0.7246 0.5608 0.0522 0.059 Uiso 1 1 calc R . . C7 C 0.5184(4) 0.6945(3) 0.0318(3) 0.0436(8) Uani 1 1 d . . . H7 H 0.5600 0.7461 -0.0086 0.052 Uiso 1 1 calc R . . C8 C 0.6658(7) 0.3904(4) 0.1701(4) 0.0696(14) Uani 1 1 d . . . H8 H 0.7697 0.3696 0.1470 0.083 Uiso 1 1 calc R . . C9 C -0.2358(4) 0.7637(3) 0.2172(2) 0.0342(7) Uani 1 1 d . . . C10 C -0.2202(5) 0.6505(3) 0.2836(3) 0.0420(8) Uani 1 1 d U . . C11 C -0.0727(7) 0.5663(4) 0.3100(4) 0.0711(12) Uani 1 1 d U . . H11 H 0.0202 0.5789 0.2840 0.085 Uiso 1 1 calc R . . C12 C -0.0597(9) 0.4631(6) 0.3745(5) 0.099(2) Uani 1 1 d U . . H12 H 0.0409 0.4074 0.3919 0.119 Uiso 1 1 calc R . . C13 C -0.1983(8) 0.4442(5) 0.4123(5) 0.0800(15) Uani 1 1 d U . . C14 C -0.3461(7) 0.5267(4) 0.3859(4) 0.0628(12) Uani 1 1 d . . . H14 H -0.4390 0.5140 0.4119 0.075 Uiso 1 1 calc R . . C15 C -0.3577(5) 0.6286(3) 0.3211(3) 0.0482(9) Uani 1 1 d . . . H15 H -0.4589 0.6833 0.3023 0.058 Uiso 1 1 calc R . . C16 C -0.1845(11) 0.3377(6) 0.4819(7) 0.139(4) Uani 1 1 d . . . H16 H -0.0834 0.2819 0.4896 0.167 Uiso 1 1 calc R . . C17 C 0.0824(5) 0.9186(3) 0.2503(3) 0.0451(9) Uani 1 1 d . . . H17 H 0.1448 0.8465 0.2440 0.054 Uiso 1 1 calc R . . C18 C -0.1118(4) 1.0748(3) 0.2349(3) 0.0429(8) Uani 1 1 d . . . H18 H -0.2102 1.1320 0.2144 0.052 Uiso 1 1 calc R . . C19 C 0.0016(5) 1.0780(3) 0.3001(3) 0.0474(9) Uani 1 1 d . . . H19 H -0.0036 1.1359 0.3330 0.057 Uiso 1 1 calc R . . C20 C 0.2852(5) 0.9413(3) 0.3673(4) 0.0543(10) Uani 1 1 d . . . H20A H 0.3721 0.9158 0.3235 0.065 Uiso 1 1 calc R . . H20B H 0.2912 0.8784 0.4238 0.065 Uiso 1 1 calc R . . C21 C 0.3068(4) 1.0363(3) 0.4085(3) 0.0440(8) Uani 1 1 d . . . C22 C 0.2494(6) 1.0521(5) 0.5028(3) 0.0635(13) Uani 1 1 d . . . H22 H 0.2012 1.0025 0.5397 0.076 Uiso 1 1 calc R . . C23 C 0.2617(7) 1.1386(5) 0.5431(4) 0.0754(14) Uani 1 1 d U . . H23 H 0.2200 1.1484 0.6059 0.090 Uiso 1 1 calc R . . C24 C 0.3346(7) 1.2098(5) 0.4914(4) 0.0726(13) Uani 1 1 d U . . H24 H 0.3433 1.2685 0.5190 0.087 Uiso 1 1 calc R . . C25 C 0.3972(6) 1.1961(4) 0.3966(4) 0.0583(11) Uani 1 1 d . . . H25 H 0.4486 1.2448 0.3618 0.070 Uiso 1 1 calc R . . C26 C 0.3816(4) 1.1086(3) 0.3547(3) 0.0401(8) Uani 1 1 d . . . C27 C 0.4552(4) 1.0954(4) 0.2542(3) 0.0442(8) Uani 1 1 d . . . H27A H 0.5219 1.1435 0.2386 0.053 Uiso 1 1 calc R . . H27B H 0.5251 1.0179 0.2609 0.053 Uiso 1 1 calc R . . C28 C 0.3371(4) 1.0636(3) 0.0987(3) 0.0374(8) Uani 1 1 d . . . H28 H 0.4125 0.9930 0.0992 0.045 Uiso 1 1 calc R . . C29 C 0.1341(5) 1.2195(3) 0.0552(3) 0.0456(9) Uani 1 1 d . . . H29 H 0.0437 1.2754 0.0192 0.055 Uiso 1 1 calc R . . C30 C 0.2068(5) 1.2234(3) 0.1422(3) 0.0464(9) Uani 1 1 d . . . H30 H 0.1761 1.2817 0.1771 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0325(3) 0.0289(3) 0.0376(3) 0.00102(19) -0.00195(18) -0.01082(19) O1 0.0333(15) 0.0455(16) 0.0733(19) 0.0038(14) 0.0113(13) -0.0033(12) O2 0.0340(13) 0.0324(12) 0.0478(14) 0.0028(10) -0.0017(10) -0.0105(10) O3 0.126(4) 0.0380(19) 0.124(4) 0.009(2) 0.035(3) 0.000(2) O4 0.0424(15) 0.0363(13) 0.0463(14) 0.0027(11) 0.0022(11) -0.0166(11) O5 0.0532(17) 0.0367(14) 0.0492(15) -0.0025(11) 0.0052(12) -0.0067(13) O6 0.158(6) 0.087(4) 0.231(8) 0.053(4) 0.058(5) -0.039(4) N1 0.0371(16) 0.0352(15) 0.0447(17) -0.0039(12) -0.0001(13) -0.0153(13) N2 0.0384(16) 0.0340(15) 0.0464(17) -0.0031(13) -0.0057(13) -0.0140(13) N3 0.0342(15) 0.0415(16) 0.0363(15) -0.0067(12) 0.0036(12) -0.0119(13) N4 0.0347(15) 0.0361(15) 0.0366(15) -0.0044(12) 0.0027(12) -0.0107(12) C1 0.0314(17) 0.0341(17) 0.0362(17) -0.0046(14) -0.0002(13) -0.0119(14) C2 0.0302(16) 0.0281(16) 0.0394(17) -0.0051(13) 0.0028(13) -0.0086(13) C3 0.042(2) 0.0365(19) 0.054(2) -0.0008(16) 0.0073(17) -0.0129(16) C4 0.066(3) 0.0310(19) 0.057(2) 0.0006(17) 0.007(2) -0.0188(18) C5 0.055(2) 0.0323(19) 0.048(2) -0.0064(16) 0.0011(18) -0.0079(17) C6 0.038(2) 0.044(2) 0.057(2) -0.0074(18) 0.0079(17) -0.0047(17) C7 0.0346(19) 0.041(2) 0.050(2) 0.0012(16) 0.0063(15) -0.0126(16) C8 0.081(4) 0.037(2) 0.074(3) -0.006(2) 0.010(3) -0.001(2) C9 0.046(2) 0.0296(17) 0.0282(16) -0.0070(13) 0.0027(14) -0.0144(15) C10 0.061(2) 0.0340(17) 0.0357(18) -0.0057(14) 0.0089(16) -0.0227(13) C11 0.0623(17) 0.0618(18) 0.078(2) 0.0025(15) 0.0105(16) -0.0164(13) C12 0.095(3) 0.092(3) 0.104(3) -0.0076(18) 0.0124(19) -0.0287(19) C13 0.082(2) 0.070(2) 0.082(2) -0.0054(16) 0.0139(17) -0.0253(17) C14 0.076(3) 0.053(3) 0.065(3) -0.006(2) 0.024(2) -0.035(2) C15 0.054(2) 0.041(2) 0.049(2) -0.0047(17) 0.0053(18) -0.0184(18) C16 0.122(7) 0.077(5) 0.179(8) 0.045(5) 0.052(6) -0.025(4) C17 0.046(2) 0.0339(18) 0.049(2) -0.0048(16) -0.0101(17) -0.0076(16) C18 0.0311(18) 0.0418(19) 0.055(2) -0.0073(16) 0.0004(16) -0.0122(15) C19 0.042(2) 0.0383(19) 0.060(2) -0.0103(17) -0.0034(18) -0.0107(16) C20 0.048(2) 0.045(2) 0.066(3) 0.0061(19) -0.018(2) -0.0201(18) C21 0.0352(18) 0.049(2) 0.044(2) -0.0046(16) -0.0079(15) -0.0125(16) C22 0.054(3) 0.086(3) 0.041(2) 0.001(2) -0.0062(19) -0.020(2) C23 0.066(3) 0.107(4) 0.044(2) -0.032(3) -0.003(2) -0.006(3) C24 0.078(3) 0.076(3) 0.065(3) -0.043(2) -0.015(2) -0.008(2) C25 0.068(3) 0.051(2) 0.062(3) -0.020(2) -0.009(2) -0.022(2) C26 0.0370(18) 0.0427(19) 0.0405(19) -0.0139(15) -0.0065(15) -0.0097(15) C27 0.0311(18) 0.058(2) 0.046(2) -0.0159(17) 0.0023(15) -0.0159(16) C28 0.0360(18) 0.0345(17) 0.0410(18) -0.0033(14) 0.0048(14) -0.0139(14) C29 0.040(2) 0.045(2) 0.043(2) -0.0066(16) 0.0034(16) -0.0044(16) C30 0.041(2) 0.044(2) 0.048(2) -0.0110(16) 0.0078(16) -0.0052(16) _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 N4 1.977(3) 2_575 ? Cu1 O2 1.982(2) 2_575 ? Cu1 N1 1.987(3) . ? Cu1 O4 2.012(3) . ? Cu1 O1 2.326(3) . ? O1 C1 1.224(4) . ? O2 C1 1.263(4) . ? O2 Cu1 1.982(2) 2_575 ? O3 C8 1.188(7) . ? O4 C9 1.273(4) . ? O5 C9 1.213(4) . ? O6 C16 1.138(9) . ? N1 C17 1.316(5) . ? N1 C18 1.368(5) . ? N2 C17 1.330(5) . ? N2 C19 1.379(5) . ? N2 C20 1.486(5) . ? N3 C28 1.340(5) . ? N3 C30 1.380(5) . ? N3 C27 1.459(4) . ? N4 C28 1.322(4) . ? N4 C29 1.388(5) . ? N4 Cu1 1.977(3) 2_575 ? C1 C2 1.504(5) . ? C2 C7 1.377(5) . ? C2 C3 1.400(5) . ? C3 C4 1.379(6) . ? C3 H3 0.9300 . ? C4 C5 1.384(6) . ? C4 H4 0.9300 . ? C5 C6 1.368(6) . ? C5 C8 1.466(6) . ? C6 C7 1.391(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.499(5) . ? C10 C11 1.378(6) . ? C10 C15 1.388(6) . ? C11 C12 1.390(9) . ? C11 H11 0.9300 . ? C12 C13 1.383(9) . ? C12 H12 0.9300 . ? C13 C14 1.371(8) . ? C13 C16 1.452(8) . ? C14 C15 1.382(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.344(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.503(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.385(6) . ? C21 C26 1.383(6) . ? C22 C23 1.366(8) . ? C22 H22 0.9300 . ? C23 C24 1.351(8) . ? C23 H23 0.9300 . ? C24 C25 1.400(7) . ? C24 H24 0.9300 . ? C25 C26 1.400(5) . ? C25 H25 0.9300 . ? C26 C27 1.504(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28 0.9300 . ? C29 C30 1.351(6) . ? C29 H29 0.9300 . ? C30 H30 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 N4 Cu1 O2 91.59(11) 2_575 2_575 ? N4 Cu1 N1 171.06(12) 2_575 . ? O2 Cu1 N1 91.53(11) 2_575 . ? N4 Cu1 O4 90.29(11) 2_575 . ? O2 Cu1 O4 151.10(11) 2_575 . ? N1 Cu1 O4 91.02(11) . . ? N4 Cu1 O1 85.24(12) 2_575 . ? O2 Cu1 O1 121.77(10) 2_575 . ? N1 Cu1 O1 86.00(12) . . ? O4 Cu1 O1 87.12(10) . . ? C1 O1 Cu1 174.3(3) . . ? C1 O2 Cu1 116.3(2) . 2_575 ? C9 O4 Cu1 108.4(2) . . ? C17 N1 C18 105.6(3) . . ? C17 N1 Cu1 124.3(3) . . ? C18 N1 Cu1 129.3(3) . . ? C17 N2 C19 107.2(3) . . ? C17 N2 C20 125.5(3) . . ? C19 N2 C20 127.3(3) . . ? C28 N3 C30 107.6(3) . . ? C28 N3 C27 126.5(3) . . ? C30 N3 C27 125.7(3) . . ? C28 N4 C29 106.5(3) . . ? C28 N4 Cu1 129.1(3) . 2_575 ? C29 N4 Cu1 124.5(3) . 2_575 ? O1 C1 O2 124.2(3) . . ? O1 C1 C2 118.4(3) . . ? O2 C1 C2 117.4(3) . . ? C7 C2 C3 119.8(3) . . ? C7 C2 C1 121.1(3) . . ? C3 C2 C1 119.1(3) . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.5(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.4(4) . . ? C6 C5 C8 120.4(4) . . ? C4 C5 C8 120.2(4) . . ? C5 C6 C7 121.2(4) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 119.4(3) . . ? C2 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? O3 C8 C5 125.1(5) . . ? O3 C8 H8 117.4 . . ? C5 C8 H8 117.4 . . ? O5 C9 O4 124.6(3) . . ? O5 C9 C10 120.1(3) . . ? O4 C9 C10 115.3(3) . . ? C11 C10 C15 118.2(4) . . ? C11 C10 C9 122.2(4) . . ? C15 C10 C9 119.6(4) . . ? C10 C11 C12 121.5(5) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 119.1(7) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 120.0(6) . . ? C14 C13 C16 120.7(6) . . ? C12 C13 C16 119.2(7) . . ? C13 C14 C15 120.3(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.8(4) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O6 C16 C13 127.5(8) . . ? O6 C16 H16 116.2 . . ? C13 C16 H16 116.2 . . ? N1 C17 N2 111.5(3) . . ? N1 C17 H17 124.3 . . ? N2 C17 H17 124.3 . . ? C19 C18 N1 110.0(3) . . ? C19 C18 H18 125.0 . . ? N1 C18 H18 125.0 . . ? C18 C19 N2 105.8(3) . . ? C18 C19 H19 127.1 . . ? N2 C19 H19 127.1 . . ? N2 C20 C21 111.3(3) . . ? N2 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? N2 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C26 119.0(4) . . ? C22 C21 C20 119.0(4) . . ? C26 C21 C20 121.9(4) . . ? C23 C22 C21 121.8(5) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C24 C23 C22 119.7(5) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 120.6(4) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 119.5(5) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C21 C26 C25 119.3(4) . . ? C21 C26 C27 123.2(3) . . ? C25 C26 C27 117.4(4) . . ? N3 C27 C26 113.4(3) . . ? N3 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? N3 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? N4 C28 N3 110.7(3) . . ? N4 C28 H28 124.7 . . ? N3 C28 H28 124.7 . . ? C30 C29 N4 108.6(3) . . ? C30 C29 H29 125.7 . . ? N4 C29 H29 125.7 . . ? C29 C30 N3 106.6(3) . . ? C29 C30 H30 126.7 . . ? N3 C30 H30 126.7 . . ? 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 N4 Cu1 O1 C1 157(3) 2_575 . . . ? O2 Cu1 O1 C1 68(3) 2_575 . . . ? N1 Cu1 O1 C1 -22(3) . . . . ? O4 Cu1 O1 C1 -113(3) . . . . ? N4 Cu1 O4 C9 -89.3(2) 2_575 . . . ? O2 Cu1 O4 C9 4.5(4) 2_575 . . . ? N1 Cu1 O4 C9 99.6(2) . . . . ? O1 Cu1 O4 C9 -174.5(2) . . . . ? N4 Cu1 N1 C17 -48.0(8) 2_575 . . . ? O2 Cu1 N1 C17 -158.4(3) 2_575 . . . ? O4 Cu1 N1 C17 50.4(3) . . . . ? O1 Cu1 N1 C17 -36.6(3) . . . . ? N4 Cu1 N1 C18 119.8(7) 2_575 . . . ? O2 Cu1 N1 C18 9.4(3) 2_575 . . . ? O4 Cu1 N1 C18 -141.8(3) . . . . ? O1 Cu1 N1 C18 131.1(3) . . . . ? Cu1 O1 C1 O2 -66(3) . . . . ? Cu1 O1 C1 C2 115(3) . . . . ? Cu1 O2 C1 O1 1.5(5) 2_575 . . . ? Cu1 O2 C1 C2 -179.3(2) 2_575 . . . ? O1 C1 C2 C7 -179.9(4) . . . . ? O2 C1 C2 C7 0.9(5) . . . . ? O1 C1 C2 C3 0.2(5) . . . . ? O2 C1 C2 C3 -179.1(3) . . . . ? C7 C2 C3 C4 -0.4(6) . . . . ? C1 C2 C3 C4 179.6(3) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C3 C4 C5 C8 179.7(4) . . . . ? C4 C5 C6 C7 1.0(6) . . . . ? C8 C5 C6 C7 -179.1(4) . . . . ? C3 C2 C7 C6 0.9(6) . . . . ? C1 C2 C7 C6 -179.1(3) . . . . ? C5 C6 C7 C2 -1.2(6) . . . . ? C6 C5 C8 O3 174.1(5) . . . . ? C4 C5 C8 O3 -6.0(8) . . . . ? Cu1 O4 C9 O5 -0.3(4) . . . . ? Cu1 O4 C9 C10 -179.9(2) . . . . ? O5 C9 C10 C11 -171.4(4) . . . . ? O4 C9 C10 C11 8.1(5) . . . . ? O5 C9 C10 C15 8.1(5) . . . . ? O4 C9 C10 C15 -172.3(3) . . . . ? C15 C10 C11 C12 -1.7(8) . . . . ? C9 C10 C11 C12 177.8(5) . . . . ? C10 C11 C12 C13 0.5(10) . . . . ? C11 C12 C13 C14 0.1(10) . . . . ? C11 C12 C13 C16 -178.3(7) . . . . ? C12 C13 C14 C15 0.4(9) . . . . ? C16 C13 C14 C15 178.8(6) . . . . ? C13 C14 C15 C10 -1.7(7) . . . . ? C11 C10 C15 C14 2.3(6) . . . . ? C9 C10 C15 C14 -177.3(4) . . . . ? C14 C13 C16 O6 -8.1(16) . . . . ? C12 C13 C16 O6 170.3(12) . . . . ? C18 N1 C17 N2 -1.4(4) . . . . ? Cu1 N1 C17 N2 168.8(2) . . . . ? C19 N2 C17 N1 1.8(5) . . . . ? C20 N2 C17 N1 -176.8(4) . . . . ? C17 N1 C18 C19 0.4(5) . . . . ? Cu1 N1 C18 C19 -169.2(3) . . . . ? N1 C18 C19 N2 0.7(5) . . . . ? C17 N2 C19 C18 -1.5(5) . . . . ? C20 N2 C19 C18 177.1(4) . . . . ? C17 N2 C20 C21 169.9(4) . . . . ? C19 N2 C20 C21 -8.5(6) . . . . ? N2 C20 C21 C22 88.0(5) . . . . ? N2 C20 C21 C26 -91.8(5) . . . . ? C26 C21 C22 C23 1.4(7) . . . . ? C20 C21 C22 C23 -178.3(4) . . . . ? C21 C22 C23 C24 -1.4(8) . . . . ? C22 C23 C24 C25 0.2(8) . . . . ? C23 C24 C25 C26 0.9(8) . . . . ? C22 C21 C26 C25 -0.2(6) . . . . ? C20 C21 C26 C25 179.5(4) . . . . ? C22 C21 C26 C27 176.9(3) . . . . ? C20 C21 C26 C27 -3.3(6) . . . . ? C24 C25 C26 C21 -0.9(6) . . . . ? C24 C25 C26 C27 -178.2(4) . . . . ? C28 N3 C27 C26 -133.3(4) . . . . ? C30 N3 C27 C26 52.5(5) . . . . ? C21 C26 C27 N3 71.8(5) . . . . ? C25 C26 C27 N3 -111.0(4) . . . . ? C29 N4 C28 N3 0.3(4) . . . . ? Cu1 N4 C28 N3 -178.6(2) 2_575 . . . ? C30 N3 C28 N4 -0.3(4) . . . . ? C27 N3 C28 N4 -175.3(3) . . . . ? C28 N4 C29 C30 -0.3(4) . . . . ? Cu1 N4 C29 C30 178.7(3) 2_575 . . . ? N4 C29 C30 N3 0.2(4) . . . . ? C28 N3 C30 C29 0.0(4) . . . . ? C27 N3 C30 C29 175.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.880 _refine_diff_density_min -0.796 _refine_diff_density_rms 0.203 _database_code_depnum_ccdc_archive 'CCDC 966843' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_20110328d_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 Cu N4 O6, C H4 O, 3(H2 O)' _chemical_formula_sum 'C31 H34 Cu N4 O10' _chemical_formula_weight 686.16 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1098(19) _cell_length_b 9.1791(11) _cell_length_c 23.866(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.424(3) _cell_angle_gamma 90.00 _cell_volume 3244.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6036 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.12 _exptl_crystal_description Prism _exptl_crystal_colour Purple _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.735 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8434 _exptl_absorpt_correction_T_max 0.8978 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20101 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5968 _reflns_number_gt 4560 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.1141P)^2^+1.6892P] 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 5968 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1771 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.28682(3) 0.20245(5) 0.253606(16) 0.02217(17) Uani 1 1 d . . . N1 N 0.1657(2) 0.1855(3) 0.27348(13) 0.0237(6) Uani 1 1 d . . . N2 N 0.0295(2) 0.1024(3) 0.27088(13) 0.0267(7) Uani 1 1 d . . . N3 N -0.4411(2) 0.1736(5) 0.25996(14) 0.0452(10) Uani 1 1 d . . . N4 N -0.5889(2) 0.1776(3) 0.24165(13) 0.0287(7) Uani 1 1 d . . . O1 O 0.24155(17) 0.1007(3) 0.18225(10) 0.0310(6) Uani 1 1 d . . . O2 O 0.2320(2) 0.3186(3) 0.14106(12) 0.0475(8) Uani 1 1 d . . . O3 O 0.0334(3) -0.0258(5) -0.11733(13) 0.0611(10) Uani 1 1 d . . . O4 O 0.32635(17) 0.3331(3) 0.31733(10) 0.0259(6) Uani 1 1 d . . . O5 O 0.35268(19) 0.1432(3) 0.37623(11) 0.0334(6) Uani 1 1 d . . . O6 O 0.4180(2) 0.6543(4) 0.60217(12) 0.0489(8) Uani 1 1 d . . . O7 O 0.3498(3) 0.4472(5) 0.07575(17) 0.0814(13) Uani 1 1 d . . . H7A H 0.3184 0.4233 0.0985 0.122 Uiso 1 1 d R . . O8 O 0.2751(3) -0.0029(4) 0.45997(14) 0.0592(9) Uani 1 1 d . . . H8A H 0.2398 0.0636 0.4440 0.089 Uiso 1 1 d R . . H8B H 0.3289 0.0295 0.4676 0.089 Uiso 1 1 d R . . O9 O 0.0975(3) 0.5452(5) 0.96910(19) 0.0837(13) Uani 1 1 d . . . H9A H 0.0670 0.4818 0.9831 0.126 Uiso 1 1 d R . . H9B H 0.0954 0.5268 0.9340 0.126 Uiso 1 1 d R . . O10 O 0.0810(3) 0.5226(5) 0.08541(16) 0.0784(12) Uani 1 1 d . . . H10A H 0.1094 0.4828 0.1159 0.118 Uiso 1 1 d R . . H10B H 0.1173 0.5747 0.0709 0.118 Uiso 1 1 d R . . C1 C 0.2222(3) 0.1843(5) 0.13874(15) 0.0320(9) Uani 1 1 d . . . C2 C 0.1851(3) 0.1106(5) 0.08271(15) 0.0326(9) Uani 1 1 d . . . C3 C 0.1644(3) 0.1929(5) 0.03310(17) 0.0418(10) Uani 1 1 d . . . H3 H 0.1774 0.2920 0.0341 0.050 Uiso 1 1 calc R . . C4 C 0.1248(3) 0.1276(5) -0.01748(17) 0.0446(11) Uani 1 1 d . . . H4 H 0.1108 0.1829 -0.0507 0.054 Uiso 1 1 calc R . . C5 C 0.1057(3) -0.0200(5) -0.01930(17) 0.0395(10) Uani 1 1 d . . . C6 C 0.1276(3) -0.1034(5) 0.03048(17) 0.0429(11) Uani 1 1 d . . . H6 H 0.1157 -0.2029 0.0295 0.052 Uiso 1 1 calc R . . C7 C 0.1669(3) -0.0369(5) 0.08119(16) 0.0360(9) Uani 1 1 d . . . H7 H 0.1813 -0.0917 0.1145 0.043 Uiso 1 1 calc R . . C8 C 0.0594(3) -0.0888(6) -0.0730(2) 0.0541(13) Uani 1 1 d . . . H8 H 0.0495 -0.1887 -0.0725 0.065 Uiso 1 1 calc R . . C9 C 0.3448(2) 0.2755(4) 0.36710(14) 0.0254(8) Uani 1 1 d . . . C10 C 0.3543(2) 0.3812(4) 0.41609(14) 0.0253(8) Uani 1 1 d . . . C11 C 0.3229(3) 0.5228(4) 0.40673(15) 0.0310(9) Uani 1 1 d . . . H11 H 0.2979 0.5532 0.3698 0.037 Uiso 1 1 calc R . . C12 C 0.3284(3) 0.6189(4) 0.45183(16) 0.0346(9) Uani 1 1 d . . . H12 H 0.3053 0.7127 0.4457 0.041 Uiso 1 1 calc R . . C13 C 0.3688(3) 0.5741(4) 0.50633(15) 0.0316(9) Uani 1 1 d . . . C14 C 0.4008(3) 0.4333(4) 0.51600(15) 0.0327(9) Uani 1 1 d . . . H14 H 0.4273 0.4037 0.5528 0.039 Uiso 1 1 calc R . . C15 C 0.3933(3) 0.3368(4) 0.47106(16) 0.0313(9) Uani 1 1 d . . . H15 H 0.4144 0.2419 0.4775 0.038 Uiso 1 1 calc R . . C16 C 0.3785(3) 0.6803(5) 0.55388(17) 0.0408(10) Uani 1 1 d . . . H16 H 0.3529 0.7721 0.5463 0.049 Uiso 1 1 calc R . . C17 C 0.0974(2) 0.1104(4) 0.24333(15) 0.0253(8) Uani 1 1 d . . . H17 H 0.0972 0.0692 0.2077 0.030 Uiso 1 1 calc R . . C18 C 0.0536(3) 0.1764(4) 0.32175(16) 0.0314(9) Uani 1 1 d . . . H18 H 0.0191 0.1889 0.3496 0.038 Uiso 1 1 calc R . . C19 C 0.1378(3) 0.2269(4) 0.32274(16) 0.0304(9) Uani 1 1 d . . . H19 H 0.1718 0.2814 0.3522 0.036 Uiso 1 1 calc R . . C20 C -0.0566(2) 0.0278(4) 0.25017(19) 0.0338(9) Uani 1 1 d . . . H20A H -0.0666 -0.0427 0.2786 0.041 Uiso 1 1 calc R . . H20B H -0.0531 -0.0250 0.2155 0.041 Uiso 1 1 calc R . . C21 C -0.1355(2) 0.1314(4) 0.23814(16) 0.0274(8) Uani 1 1 d . . . C22 C -0.2054(3) 0.1160(5) 0.26740(16) 0.0353(9) Uani 1 1 d . . . H22 H -0.2025 0.0425 0.2945 0.042 Uiso 1 1 calc R . . C23 C -0.2791(3) 0.2075(6) 0.25715(17) 0.0438(12) Uani 1 1 d . . . C24 C -0.2835(3) 0.3166(5) 0.21622(19) 0.0449(11) Uani 1 1 d . . . H24 H -0.3328 0.3794 0.2091 0.054 Uiso 1 1 calc R . . C25 C -0.2146(3) 0.3320(5) 0.18592(19) 0.0406(10) Uani 1 1 d . . . H25 H -0.2185 0.4030 0.1577 0.049 Uiso 1 1 calc R . . C26 C -0.1402(3) 0.2415(5) 0.19779(16) 0.0327(9) Uani 1 1 d . . . H26 H -0.0929 0.2544 0.1786 0.039 Uiso 1 1 calc R . . C27 C -0.3493(3) 0.1916(10) 0.2931(2) 0.087(3) Uani 1 1 d . . . H27A H -0.3344 0.1079 0.3180 0.104 Uiso 1 1 calc R . . H27B H -0.3477 0.2772 0.3172 0.104 Uiso 1 1 calc R . . C28 C -0.5161(3) 0.2189(5) 0.27730(16) 0.0386(10) Uani 1 1 d . . . H28 H -0.5161 0.2726 0.3103 0.046 Uiso 1 1 calc R . . C29 C -0.5587(3) 0.0993(5) 0.19942(19) 0.0486(12) Uani 1 1 d . . . H29 H -0.5955 0.0551 0.1682 0.058 Uiso 1 1 calc R . . C30 C -0.4677(3) 0.0974(6) 0.21066(19) 0.0492(12) Uani 1 1 d . . . H30 H -0.4305 0.0527 0.1890 0.059 Uiso 1 1 calc R . . C31 C 0.4479(6) 0.4366(9) 0.1045(3) 0.102(3) Uani 1 1 d . . . H31A H 0.4851 0.4488 0.0765 0.153 Uiso 1 1 calc R . . H31B H 0.4593 0.3429 0.1223 0.153 Uiso 1 1 calc R . . H31C H 0.4618 0.5115 0.1330 0.153 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0187(3) 0.0289(3) 0.0192(2) -0.00329(16) 0.00450(17) -0.00084(18) N1 0.0156(15) 0.0268(16) 0.0281(15) -0.0027(12) 0.0031(12) 0.0008(13) N2 0.0159(15) 0.0287(16) 0.0357(16) -0.0018(13) 0.0059(13) 0.0012(13) N3 0.0217(18) 0.084(3) 0.0313(18) -0.0043(18) 0.0093(15) 0.0123(19) N4 0.0228(17) 0.0367(18) 0.0275(16) -0.0094(13) 0.0071(13) -0.0012(14) O1 0.0260(14) 0.0421(16) 0.0239(13) -0.0043(11) 0.0028(11) -0.0055(12) O2 0.067(2) 0.041(2) 0.0319(16) -0.0056(12) 0.0036(15) -0.0084(16) O3 0.060(2) 0.090(3) 0.0291(16) -0.0123(17) -0.0019(15) 0.005(2) O4 0.0216(13) 0.0331(14) 0.0240(13) -0.0048(10) 0.0065(10) -0.0040(11) O5 0.0400(17) 0.0309(15) 0.0299(14) -0.0043(11) 0.0078(12) 0.0040(13) O6 0.068(2) 0.0519(19) 0.0249(15) -0.0095(13) 0.0052(15) -0.0089(17) O7 0.090(3) 0.093(3) 0.059(2) 0.013(2) 0.008(2) -0.037(3) O8 0.069(3) 0.053(2) 0.058(2) -0.0004(16) 0.0188(19) -0.0079(19) O9 0.092(3) 0.081(3) 0.084(3) 0.009(2) 0.033(3) 0.016(3) O10 0.081(3) 0.094(3) 0.059(2) -0.012(2) 0.010(2) 0.018(3) C1 0.026(2) 0.048(3) 0.0221(19) -0.0043(16) 0.0065(16) -0.0051(19) C2 0.029(2) 0.046(2) 0.0236(18) -0.0079(16) 0.0068(16) -0.0070(19) C3 0.050(3) 0.044(3) 0.031(2) -0.0015(17) 0.007(2) -0.007(2) C4 0.052(3) 0.057(3) 0.024(2) 0.0008(19) 0.0052(19) -0.001(2) C5 0.035(2) 0.053(3) 0.029(2) -0.0126(18) 0.0051(18) 0.001(2) C6 0.049(3) 0.042(2) 0.035(2) -0.0105(18) 0.003(2) 0.000(2) C7 0.037(2) 0.041(2) 0.028(2) -0.0040(16) 0.0018(17) -0.001(2) C8 0.051(3) 0.063(3) 0.045(3) -0.019(2) 0.001(2) 0.002(3) C9 0.0150(18) 0.039(2) 0.0228(18) -0.0055(15) 0.0050(14) -0.0031(16) C10 0.0242(19) 0.030(2) 0.0235(17) -0.0029(14) 0.0088(15) -0.0029(16) C11 0.035(2) 0.037(2) 0.0191(17) -0.0009(14) 0.0028(16) 0.0033(18) C12 0.041(2) 0.031(2) 0.0300(19) -0.0033(16) 0.0037(17) 0.0036(19) C13 0.036(2) 0.036(2) 0.0239(18) -0.0049(15) 0.0086(16) -0.0056(18) C14 0.038(2) 0.039(2) 0.0193(17) 0.0020(15) 0.0014(16) -0.0025(19) C15 0.031(2) 0.031(2) 0.030(2) -0.0004(15) 0.0015(17) 0.0006(17) C16 0.055(3) 0.038(2) 0.031(2) -0.0087(17) 0.011(2) -0.005(2) C17 0.0180(18) 0.0260(19) 0.0313(18) -0.0022(14) 0.0032(15) -0.0006(16) C18 0.025(2) 0.043(2) 0.0287(19) -0.0018(16) 0.0116(16) 0.0042(18) C19 0.024(2) 0.040(2) 0.0270(19) -0.0075(15) 0.0042(16) 0.0013(17) C20 0.0153(19) 0.030(2) 0.055(2) -0.0056(17) 0.0057(17) -0.0028(16) C21 0.0128(17) 0.031(2) 0.037(2) -0.0100(16) 0.0013(15) -0.0029(16) C22 0.021(2) 0.056(3) 0.0283(19) 0.0002(17) 0.0028(16) -0.0037(19) C23 0.019(2) 0.082(4) 0.029(2) -0.017(2) 0.0032(17) 0.010(2) C24 0.029(2) 0.053(3) 0.046(3) -0.019(2) -0.008(2) 0.016(2) C25 0.043(3) 0.031(2) 0.043(2) -0.0023(17) -0.002(2) -0.004(2) C26 0.030(2) 0.034(2) 0.036(2) -0.0024(16) 0.0091(18) -0.0055(18) C27 0.017(2) 0.211(9) 0.032(2) -0.011(3) 0.0034(19) 0.021(4) C28 0.020(2) 0.069(3) 0.028(2) -0.0133(19) 0.0062(17) 0.003(2) C29 0.039(3) 0.065(3) 0.047(3) -0.028(2) 0.019(2) -0.005(2) C30 0.035(3) 0.071(3) 0.047(3) -0.020(2) 0.022(2) 0.006(2) C31 0.128(7) 0.079(5) 0.092(5) -0.006(4) 0.004(5) -0.017(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.936(2) . ? Cu1 O1 1.944(2) . ? Cu1 N4 1.968(3) 1_655 ? Cu1 N1 1.985(3) . ? N1 C17 1.328(5) . ? N1 C19 1.379(4) . ? N2 C17 1.326(4) . ? N2 C18 1.376(5) . ? N2 C20 1.467(5) . ? N3 C28 1.347(5) . ? N3 C30 1.360(6) . ? N3 C27 1.464(6) . ? N4 C28 1.306(5) . ? N4 C29 1.386(5) . ? N4 Cu1 1.968(3) 1_455 ? O1 C1 1.277(5) . ? O2 C1 1.242(5) . ? O3 C8 1.201(6) . ? O4 C9 1.279(4) . ? O5 C9 1.236(5) . ? O6 C16 1.212(5) . ? O7 C31 1.508(9) . ? O7 H7A 0.8200 . ? O8 H8A 0.8499 . ? O8 H8B 0.8500 . ? O9 H9A 0.8499 . ? O9 H9B 0.8501 . ? O10 H10A 0.8501 . ? O10 H10B 0.8500 . ? C1 C2 1.505(5) . ? C2 C7 1.380(6) . ? C2 C3 1.387(6) . ? C3 C4 1.374(6) . ? C3 H3 0.9300 . ? C4 C5 1.384(7) . ? C4 H4 0.9300 . ? C5 C6 1.397(6) . ? C5 C8 1.475(6) . ? C6 C7 1.381(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.504(5) . ? C10 C11 1.386(5) . ? C10 C15 1.388(5) . ? C11 C12 1.381(5) . ? C11 H11 0.9300 . ? C12 C13 1.385(5) . ? C12 H12 0.9300 . ? C13 C14 1.383(6) . ? C13 C16 1.481(5) . ? C14 C15 1.378(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.350(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.508(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.383(5) . ? C21 C26 1.388(6) . ? C22 C23 1.378(6) . ? C22 H22 0.9300 . ? C23 C24 1.391(7) . ? C23 C27 1.499(6) . ? C24 C25 1.387(6) . ? C24 H24 0.9300 . ? C25 C26 1.382(6) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28 0.9300 . ? C29 C30 1.348(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? 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 O4 Cu1 O1 170.43(11) . . ? O4 Cu1 N4 91.77(11) . 1_655 ? O1 Cu1 N4 89.87(11) . 1_655 ? O4 Cu1 N1 90.95(11) . . ? O1 Cu1 N1 89.46(11) . . ? N4 Cu1 N1 167.62(13) 1_655 . ? C17 N1 C19 105.6(3) . . ? C17 N1 Cu1 124.4(2) . . ? C19 N1 Cu1 129.4(3) . . ? C17 N2 C18 108.4(3) . . ? C17 N2 C20 125.5(3) . . ? C18 N2 C20 126.1(3) . . ? C28 N3 C30 107.6(4) . . ? C28 N3 C27 124.3(4) . . ? C30 N3 C27 127.7(4) . . ? C28 N4 C29 105.6(3) . . ? C28 N4 Cu1 125.2(2) . 1_455 ? C29 N4 Cu1 128.8(3) . 1_455 ? C1 O1 Cu1 114.1(3) . . ? C9 O4 Cu1 116.8(2) . . ? C31 O7 H7A 109.2 . . ? H8A O8 H8B 109.5 . . ? H9A O9 H9B 109.5 . . ? H10A O10 H10B 109.5 . . ? O2 C1 O1 123.6(4) . . ? O2 C1 C2 120.4(4) . . ? O1 C1 C2 115.9(4) . . ? C7 C2 C3 120.1(4) . . ? C7 C2 C1 120.1(4) . . ? C3 C2 C1 119.7(4) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 C8 120.4(4) . . ? C6 C5 C8 119.8(4) . . ? C7 C6 C5 119.5(4) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C2 C7 C6 120.4(4) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O3 C8 C5 125.1(5) . . ? O3 C8 H8 117.4 . . ? C5 C8 H8 117.4 . . ? O5 C9 O4 124.4(3) . . ? O5 C9 C10 120.4(3) . . ? O4 C9 C10 115.2(3) . . ? C11 C10 C15 119.7(3) . . ? C11 C10 C9 120.2(3) . . ? C15 C10 C9 120.2(3) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.3(4) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 120.6(3) . . ? C14 C13 C16 120.6(4) . . ? C12 C13 C16 118.8(4) . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 120.1(4) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? O6 C16 C13 123.7(4) . . ? O6 C16 H16 118.2 . . ? C13 C16 H16 118.2 . . ? N2 C17 N1 110.8(3) . . ? N2 C17 H17 124.6 . . ? N1 C17 H17 124.6 . . ? C19 C18 N2 105.6(3) . . ? C19 C18 H18 127.2 . . ? N2 C18 H18 127.2 . . ? C18 C19 N1 109.7(3) . . ? C18 C19 H19 125.2 . . ? N1 C19 H19 125.2 . . ? N2 C20 C21 112.6(3) . . ? N2 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? N2 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C26 119.0(4) . . ? C22 C21 C20 119.6(4) . . ? C26 C21 C20 121.4(3) . . ? C23 C22 C21 121.3(4) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 119.2(4) . . ? C22 C23 C27 118.6(5) . . ? C24 C23 C27 122.1(5) . . ? C25 C24 C23 120.2(4) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 119.7(4) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C21 120.5(4) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? N3 C27 C23 113.8(4) . . ? N3 C27 H27A 108.8 . . ? C23 C27 H27A 108.8 . . ? N3 C27 H27B 108.8 . . ? C23 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? N4 C28 N3 111.2(3) . . ? N4 C28 H28 124.4 . . ? N3 C28 H28 124.4 . . ? C30 C29 N4 109.4(4) . . ? C30 C29 H29 125.3 . . ? N4 C29 H29 125.3 . . ? C29 C30 N3 106.3(3) . . ? C29 C30 H30 126.9 . . ? N3 C30 H30 126.9 . . ? O7 C31 H31A 109.5 . . ? O7 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O7 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? 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 O4 Cu1 N1 C17 176.9(3) . . . . ? O1 Cu1 N1 C17 6.5(3) . . . . ? N4 Cu1 N1 C17 -80.4(6) 1_655 . . . ? O4 Cu1 N1 C19 -13.3(3) . . . . ? O1 Cu1 N1 C19 176.3(3) . . . . ? N4 Cu1 N1 C19 89.4(6) 1_655 . . . ? O4 Cu1 O1 C1 8.4(8) . . . . ? N4 Cu1 O1 C1 -91.5(3) 1_655 . . . ? N1 Cu1 O1 C1 100.9(3) . . . . ? O1 Cu1 O4 C9 168.1(5) . . . . ? N4 Cu1 O4 C9 -92.2(2) 1_655 . . . ? N1 Cu1 O4 C9 75.7(2) . . . . ? Cu1 O1 C1 O2 0.7(5) . . . . ? Cu1 O1 C1 C2 -178.7(2) . . . . ? O2 C1 C2 C7 -174.3(4) . . . . ? O1 C1 C2 C7 5.2(5) . . . . ? O2 C1 C2 C3 2.1(6) . . . . ? O1 C1 C2 C3 -178.4(4) . . . . ? C7 C2 C3 C4 0.8(7) . . . . ? C1 C2 C3 C4 -175.6(4) . . . . ? C2 C3 C4 C5 -0.3(7) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? C3 C4 C5 C8 177.1(4) . . . . ? C4 C5 C6 C7 0.9(7) . . . . ? C8 C5 C6 C7 -176.8(4) . . . . ? C3 C2 C7 C6 -0.5(6) . . . . ? C1 C2 C7 C6 175.9(4) . . . . ? C5 C6 C7 C2 -0.4(6) . . . . ? C4 C5 C8 O3 -1.8(7) . . . . ? C6 C5 C8 O3 175.9(5) . . . . ? Cu1 O4 C9 O5 11.8(5) . . . . ? Cu1 O4 C9 C10 -166.5(2) . . . . ? O5 C9 C10 C11 -163.1(4) . . . . ? O4 C9 C10 C11 15.2(5) . . . . ? O5 C9 C10 C15 15.9(5) . . . . ? O4 C9 C10 C15 -165.7(3) . . . . ? C15 C10 C11 C12 -1.4(6) . . . . ? C9 C10 C11 C12 177.7(4) . . . . ? C10 C11 C12 C13 2.4(6) . . . . ? C11 C12 C13 C14 -2.0(6) . . . . ? C11 C12 C13 C16 177.0(4) . . . . ? C12 C13 C14 C15 0.6(6) . . . . ? C16 C13 C14 C15 -178.4(4) . . . . ? C13 C14 C15 C10 0.4(6) . . . . ? C11 C10 C15 C14 -0.1(6) . . . . ? C9 C10 C15 C14 -179.1(3) . . . . ? C14 C13 C16 O6 4.0(7) . . . . ? C12 C13 C16 O6 -175.1(4) . . . . ? C18 N2 C17 N1 0.3(4) . . . . ? C20 N2 C17 N1 -180.0(3) . . . . ? C19 N1 C17 N2 -0.3(4) . . . . ? Cu1 N1 C17 N2 171.5(2) . . . . ? C17 N2 C18 C19 -0.2(4) . . . . ? C20 N2 C18 C19 -179.9(4) . . . . ? N2 C18 C19 N1 0.0(4) . . . . ? C17 N1 C19 C18 0.2(4) . . . . ? Cu1 N1 C19 C18 -171.1(3) . . . . ? C17 N2 C20 C21 -114.2(4) . . . . ? C18 N2 C20 C21 65.5(5) . . . . ? N2 C20 C21 C22 -120.1(4) . . . . ? N2 C20 C21 C26 60.6(5) . . . . ? C26 C21 C22 C23 0.1(6) . . . . ? C20 C21 C22 C23 -179.3(4) . . . . ? C21 C22 C23 C24 0.5(6) . . . . ? C21 C22 C23 C27 -175.8(4) . . . . ? C22 C23 C24 C25 0.4(7) . . . . ? C27 C23 C24 C25 176.7(4) . . . . ? C23 C24 C25 C26 -2.0(6) . . . . ? C24 C25 C26 C21 2.6(6) . . . . ? C22 C21 C26 C25 -1.7(6) . . . . ? C20 C21 C26 C25 177.7(4) . . . . ? C28 N3 C27 C23 -149.7(5) . . . . ? C30 N3 C27 C23 37.8(9) . . . . ? C22 C23 C27 N3 -126.7(6) . . . . ? C24 C23 C27 N3 57.0(8) . . . . ? C29 N4 C28 N3 0.9(5) . . . . ? Cu1 N4 C28 N3 173.6(3) 1_455 . . . ? C30 N3 C28 N4 -0.8(6) . . . . ? C27 N3 C28 N4 -174.5(5) . . . . ? C28 N4 C29 C30 -0.7(6) . . . . ? Cu1 N4 C29 C30 -173.1(3) 1_455 . . . ? N4 C29 C30 N3 0.3(6) . . . . ? C28 N3 C30 C29 0.3(6) . . . . ? C27 N3 C30 C29 173.7(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 O10 H10B O9 0.85 2.40 2.843(6) 112.7 1_554 O10 H10A O2 0.85 2.37 3.046(6) 136.6 . O7 H7A O2 0.82 2.04 2.845(5) 165.0 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.676 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 966854' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 Cu N4 O6, H2 O' _chemical_formula_sum 'C30 H26 Cu N4 O7' _chemical_formula_weight 618.09 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' Cu Cu 0.3201 1.2651 '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' _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' _cell_length_a 10.7315(9) _cell_length_b 10.9239(9) _cell_length_c 12.9081(18) _cell_angle_alpha 104.097(3) _cell_angle_beta 104.031(3) _cell_angle_gamma 104.282(2) _cell_volume 1346.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2529 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 23.67 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 0.868 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8253 _exptl_absorpt_correction_T_max 0.9030 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11015 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4725 _reflns_number_gt 3378 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.1578P)^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 4725 _refine_ls_number_parameters 379 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2296 _refine_ls_wR_factor_gt 0.1970 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.00677(6) 0.65765(6) 0.15285(5) 0.0352(3) Uani 1 1 d U . . O1 O 0.0291(4) 0.6468(4) 0.3060(3) 0.0382(9) Uani 1 1 d . . . O2 O 0.0164(5) 0.8510(4) 0.3441(3) 0.0595(13) Uani 1 1 d . . . O3 O 0.2433(5) 0.9092(5) 0.9222(3) 0.0587(12) Uani 1 1 d . . . O4 O -0.0546(4) 0.7334(5) 0.0247(4) 0.0591(10) Uani 1 1 d U . . O5 O -0.0304(6) 0.5610(6) -0.0866(5) 0.0833(14) Uani 1 1 d U . . O6 O -0.2928(6) 0.7468(7) -0.5506(4) 0.0908(19) Uani 1 1 d . . . O7 O 0.2861(5) 0.1856(5) 0.9336(5) 0.0795(16) Uani 1 1 d . . . H7A H 0.2793 0.1971 0.8699 0.119 Uiso 1 1 d R . . H7B H 0.2592 0.1235 0.9600 0.119 Uiso 1 1 d R . . N1 N 0.1909(4) 0.7463(4) 0.1900(3) 0.0323(10) Uani 1 1 d . . . N2 N 0.3883(4) 0.8717(4) 0.1955(4) 0.0383(11) Uani 1 1 d . . . N3 N 0.6026(4) 1.4674(4) 0.1370(4) 0.0384(11) Uani 1 1 d . . . N4 N 0.7997(4) 1.5533(4) 0.1184(4) 0.0362(10) Uani 1 1 d . . . C1 C 0.0393(5) 0.7600(5) 0.3744(4) 0.0329(12) Uani 1 1 d . . . C2 C 0.0825(5) 0.7725(5) 0.4971(4) 0.0313(11) Uani 1 1 d . . . C3 C 0.1033(5) 0.8921(5) 0.5775(4) 0.0348(12) Uani 1 1 d . . . H3 H 0.0906 0.9643 0.5554 0.042 Uiso 1 1 calc R . . C4 C 0.1430(5) 0.9042(5) 0.6906(4) 0.0386(13) Uani 1 1 d . . . H4 H 0.1580 0.9849 0.7445 0.046 Uiso 1 1 calc R . . C5 C 0.1605(5) 0.7975(5) 0.7242(4) 0.0351(12) Uani 1 1 d . . . C6 C 0.1397(5) 0.6774(6) 0.6431(5) 0.0407(13) Uani 1 1 d . . . H6 H 0.1520 0.6051 0.6651 0.049 Uiso 1 1 calc R . . C7 C 0.1013(5) 0.6657(5) 0.5311(4) 0.0355(12) Uani 1 1 d . . . H7 H 0.0877 0.5853 0.4773 0.043 Uiso 1 1 calc R . . C8 C 0.2063(6) 0.8075(7) 0.8440(5) 0.0467(15) Uani 1 1 d . . . H8 H 0.2067 0.7293 0.8606 0.056 Uiso 1 1 calc R . . C9 C -0.0628(6) 0.6642(7) -0.0674(5) 0.0518(11) Uani 1 1 d U . . C10 C -0.1129(6) 0.7136(7) -0.1646(5) 0.0500(14) Uani 1 1 d U . . C11 C -0.1480(6) 0.6244(6) -0.2706(6) 0.0562(18) Uani 1 1 d . . . H11 H -0.1405 0.5399 -0.2786 0.067 Uiso 1 1 calc R . . C12 C -0.1933(6) 0.6578(6) -0.3633(6) 0.0507(16) Uani 1 1 d . . . H12 H -0.2214 0.5943 -0.4343 0.061 Uiso 1 1 calc R . . C13 C -0.1984(5) 0.7818(6) -0.3543(5) 0.0400(13) Uani 1 1 d . . . C14 C -0.1592(6) 0.8770(5) -0.2506(5) 0.0418(13) Uani 1 1 d . . . H14 H -0.1590 0.9635 -0.2449 0.050 Uiso 1 1 calc R . . C15 C -0.1195(6) 0.8419(6) -0.1538(5) 0.0493(15) Uani 1 1 d . . . H15 H -0.0977 0.9033 -0.0827 0.059 Uiso 1 1 calc R . . C16 C -0.2455(7) 0.8186(8) -0.4578(6) 0.0623(19) Uani 1 1 d . . . H16 H -0.2359 0.9082 -0.4469 0.075 Uiso 1 1 calc R . . C17 C 0.2534(5) 0.8321(5) 0.1491(4) 0.0333(12) Uani 1 1 d . . . H17 H 0.2091 0.8621 0.0941 0.040 Uiso 1 1 calc R . . C18 C 0.2937(6) 0.7316(6) 0.2688(5) 0.0490(16) Uani 1 1 d . . . H18 H 0.2807 0.6767 0.3127 0.059 Uiso 1 1 calc R . . C19 C 0.4143(6) 0.8072(6) 0.2732(6) 0.0528(17) Uani 1 1 d . . . H19 H 0.4989 0.8147 0.3195 0.063 Uiso 1 1 calc R . . C20 C 0.4872(6) 0.9753(6) 0.1756(5) 0.0441(14) Uani 1 1 d . . . H20A H 0.4584 0.9664 0.0961 0.053 Uiso 1 1 calc R . . H20B H 0.5744 0.9608 0.1936 0.053 Uiso 1 1 calc R . . C21 C 0.5045(5) 1.1131(5) 0.2424(5) 0.0379(13) Uani 1 1 d . . . C22 C 0.5370(6) 1.1532(6) 0.3599(5) 0.0478(15) Uani 1 1 d . . . H22 H 0.5473 1.0925 0.3981 0.057 Uiso 1 1 calc R . . C23 C 0.5536(6) 1.2808(6) 0.4178(5) 0.0509(16) Uani 1 1 d . . . H23 H 0.5742 1.3056 0.4958 0.061 Uiso 1 1 calc R . . C24 C 0.5409(6) 1.3758(6) 0.3653(5) 0.0443(14) Uani 1 1 d . . . H24 H 0.5530 1.4628 0.4068 0.053 Uiso 1 1 calc R . . C25 C 0.5100(5) 1.3377(6) 0.2495(5) 0.0392(13) Uani 1 1 d . . . C26 C 0.4916(5) 1.2065(6) 0.1894(5) 0.0394(13) Uani 1 1 d . . . H26 H 0.4701 1.1813 0.1113 0.047 Uiso 1 1 calc R . . C27 C 0.4967(6) 1.4403(6) 0.1902(6) 0.0479(15) Uani 1 1 d . . . H27A H 0.4081 1.4079 0.1330 0.058 Uiso 1 1 calc R . . H27B H 0.5034 1.5226 0.2444 0.058 Uiso 1 1 calc R . . C28 C 0.7278(6) 1.5571(6) 0.1880(5) 0.0419(14) Uani 1 1 d . . . H28 H 0.7593 1.6140 0.2621 0.050 Uiso 1 1 calc R . . C29 C 0.5957(5) 1.4040(5) 0.0293(5) 0.0408(13) Uani 1 1 d . . . H29 H 0.5213 1.3367 -0.0258 0.049 Uiso 1 1 calc R . . C30 C 0.7168(6) 1.4574(5) 0.0183(5) 0.0405(13) Uani 1 1 d . . . H30 H 0.7406 1.4334 -0.0466 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0335(4) 0.0412(4) 0.0251(4) 0.0154(3) 0.0064(3) 0.0008(3) O1 0.051(2) 0.039(2) 0.0230(18) 0.0107(16) 0.0108(17) 0.0107(17) O2 0.104(4) 0.057(3) 0.031(2) 0.023(2) 0.020(2) 0.044(3) O3 0.068(3) 0.065(3) 0.021(2) 0.007(2) 0.005(2) 0.000(2) O4 0.053(3) 0.091(3) 0.0366(15) 0.0360(15) 0.013(2) 0.014(2) O5 0.089(2) 0.0783(18) 0.088(2) 0.0394(15) 0.0175(16) 0.0343(17) O6 0.088(4) 0.138(5) 0.035(3) 0.035(3) 0.012(3) 0.018(4) O7 0.071(3) 0.070(3) 0.074(4) 0.012(3) 0.005(3) 0.013(3) N1 0.039(2) 0.031(2) 0.024(2) 0.0138(17) 0.0064(19) 0.0051(18) N2 0.032(2) 0.038(2) 0.040(3) 0.016(2) 0.006(2) 0.0043(19) N3 0.035(2) 0.046(3) 0.039(3) 0.023(2) 0.015(2) 0.008(2) N4 0.040(3) 0.037(2) 0.030(2) 0.0157(19) 0.012(2) 0.0037(19) C1 0.042(3) 0.035(3) 0.019(2) 0.005(2) 0.011(2) 0.010(2) C2 0.030(3) 0.036(3) 0.027(3) 0.012(2) 0.009(2) 0.008(2) C3 0.042(3) 0.037(3) 0.022(3) 0.009(2) 0.006(2) 0.011(2) C4 0.042(3) 0.040(3) 0.028(3) 0.004(2) 0.015(2) 0.005(2) C5 0.025(3) 0.046(3) 0.025(3) 0.012(2) 0.003(2) 0.002(2) C6 0.038(3) 0.047(3) 0.035(3) 0.020(3) 0.008(2) 0.008(2) C7 0.042(3) 0.035(3) 0.028(3) 0.010(2) 0.013(2) 0.008(2) C8 0.037(3) 0.068(4) 0.030(3) 0.020(3) 0.007(3) 0.007(3) C9 0.055(2) 0.0606(18) 0.0408(11) 0.0311(13) 0.0116(15) 0.0093(15) C10 0.034(3) 0.079(4) 0.040(2) 0.038(3) 0.012(3) 0.006(3) C11 0.044(4) 0.045(3) 0.079(5) 0.031(3) 0.013(3) 0.009(3) C12 0.041(3) 0.040(3) 0.053(4) 0.005(3) 0.001(3) 0.005(3) C13 0.031(3) 0.053(3) 0.032(3) 0.017(3) 0.008(2) 0.006(2) C14 0.056(4) 0.035(3) 0.040(3) 0.015(2) 0.018(3) 0.018(3) C15 0.053(4) 0.062(4) 0.025(3) 0.006(3) 0.009(3) 0.017(3) C16 0.061(4) 0.083(5) 0.038(4) 0.029(4) 0.008(3) 0.012(4) C17 0.031(3) 0.037(3) 0.031(3) 0.011(2) 0.010(2) 0.007(2) C18 0.046(3) 0.047(3) 0.047(4) 0.028(3) 0.003(3) 0.004(3) C19 0.037(3) 0.053(3) 0.060(4) 0.033(3) -0.003(3) 0.005(3) C20 0.033(3) 0.046(3) 0.051(4) 0.024(3) 0.012(3) 0.004(2) C21 0.023(3) 0.048(3) 0.042(3) 0.020(3) 0.014(2) 0.002(2) C22 0.036(3) 0.059(4) 0.049(4) 0.031(3) 0.011(3) 0.006(3) C23 0.043(3) 0.063(4) 0.037(3) 0.018(3) 0.006(3) 0.006(3) C24 0.038(3) 0.049(3) 0.041(3) 0.013(3) 0.014(3) 0.008(2) C25 0.028(3) 0.046(3) 0.052(4) 0.029(3) 0.016(3) 0.010(2) C26 0.027(3) 0.054(3) 0.037(3) 0.023(3) 0.009(2) 0.006(2) C27 0.039(3) 0.054(3) 0.067(4) 0.039(3) 0.023(3) 0.019(3) C28 0.043(3) 0.045(3) 0.033(3) 0.016(2) 0.012(3) 0.002(2) C29 0.035(3) 0.035(3) 0.045(3) 0.014(2) 0.008(3) 0.004(2) C30 0.041(3) 0.038(3) 0.039(3) 0.012(2) 0.012(3) 0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.958(3) . ? Cu1 N1 1.984(4) . ? Cu1 N4 1.987(4) 1_445 ? Cu1 O4 2.037(4) . ? O1 C1 1.294(6) . ? O2 C1 1.211(6) . ? O3 C8 1.205(8) . ? O4 C9 1.213(8) . ? O5 C9 1.245(8) . ? O6 C16 1.166(9) . ? O7 H7A 0.8502 . ? O7 H7B 0.8501 . ? N1 C17 1.307(6) . ? N1 C18 1.378(7) . ? N2 C17 1.336(6) . ? N2 C19 1.373(7) . ? N2 C20 1.467(6) . ? N3 C28 1.344(7) . ? N3 C29 1.369(8) . ? N3 C27 1.470(7) . ? N4 C28 1.318(7) . ? N4 C30 1.372(7) . ? N4 Cu1 1.987(4) 1_665 ? C1 C2 1.500(7) . ? C2 C7 1.385(7) . ? C2 C3 1.384(7) . ? C3 C4 1.381(7) . ? C3 H3 0.9300 . ? C4 C5 1.377(8) . ? C4 H4 0.9300 . ? C5 C6 1.393(8) . ? C5 C8 1.473(7) . ? C6 C7 1.368(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.517(8) . ? C10 C11 1.372(10) . ? C10 C15 1.395(9) . ? C11 C12 1.349(9) . ? C11 H11 0.9300 . ? C12 C13 1.347(8) . ? C12 H12 0.9300 . ? C13 C14 1.372(8) . ? C13 C16 1.495(8) . ? C14 C15 1.395(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.332(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.482(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C26 1.376(8) . ? C21 C22 1.398(8) . ? C22 C23 1.357(9) . ? C22 H22 0.9300 . ? C23 C24 1.386(8) . ? C23 H23 0.9300 . ? C24 C25 1.380(8) . ? C24 H24 0.9300 . ? C25 C26 1.392(9) . ? C25 C27 1.519(7) . ? C26 H26 0.9300 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28 0.9300 . ? C29 C30 1.344(8) . ? C29 H29 0.9300 . ? C30 H30 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 N1 88.44(16) . . ? O1 Cu1 N4 88.85(16) . 1_445 ? N1 Cu1 N4 174.32(16) . 1_445 ? O1 Cu1 O4 158.20(19) . . ? N1 Cu1 O4 92.66(17) . . ? N4 Cu1 O4 91.72(17) 1_445 . ? C1 O1 Cu1 109.0(3) . . ? C9 O4 Cu1 115.4(5) . . ? H7A O7 H7B 138.9 . . ? C17 N1 C18 104.6(4) . . ? C17 N1 Cu1 129.1(4) . . ? C18 N1 Cu1 126.3(3) . . ? C17 N2 C19 106.6(4) . . ? C17 N2 C20 126.0(4) . . ? C19 N2 C20 127.0(5) . . ? C28 N3 C29 107.0(5) . . ? C28 N3 C27 125.6(5) . . ? C29 N3 C27 127.3(5) . . ? C28 N4 C30 106.5(4) . . ? C28 N4 Cu1 127.2(4) . 1_665 ? C30 N4 Cu1 126.2(4) . 1_665 ? O2 C1 O1 123.8(5) . . ? O2 C1 C2 121.0(5) . . ? O1 C1 C2 115.2(4) . . ? C7 C2 C3 119.5(5) . . ? C7 C2 C1 120.8(5) . . ? C3 C2 C1 119.7(4) . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.5(5) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.4(5) . . ? C4 C5 C8 122.1(5) . . ? C6 C5 C8 118.4(5) . . ? C7 C6 C5 120.1(5) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 120.6(5) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? O3 C8 C5 124.9(6) . . ? O3 C8 H8 117.5 . . ? C5 C8 H8 117.5 . . ? O4 C9 O5 125.6(6) . . ? O4 C9 C10 115.3(6) . . ? O5 C9 C10 119.1(6) . . ? C11 C10 C15 119.0(5) . . ? C11 C10 C9 115.7(6) . . ? C15 C10 C9 125.3(6) . . ? C12 C11 C10 120.9(6) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.8(6) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.9(5) . . ? C12 C13 C16 120.3(6) . . ? C14 C13 C16 118.8(6) . . ? C13 C14 C15 119.0(5) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C10 C15 C14 119.3(5) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? O6 C16 C13 126.9(8) . . ? O6 C16 H16 116.6 . . ? C13 C16 H16 116.6 . . ? N1 C17 N2 112.3(5) . . ? N1 C17 H17 123.9 . . ? N2 C17 H17 123.9 . . ? C19 C18 N1 110.5(5) . . ? C19 C18 H18 124.7 . . ? N1 C18 H18 124.7 . . ? C18 C19 N2 106.1(5) . . ? C18 C19 H19 127.0 . . ? N2 C19 H19 127.0 . . ? N2 C20 C21 113.8(5) . . ? N2 C20 H20A 108.8 . . ? C21 C20 H20A 108.8 . . ? N2 C20 H20B 108.8 . . ? C21 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C26 C21 C22 118.1(6) . . ? C26 C21 C20 120.0(5) . . ? C22 C21 C20 121.8(5) . . ? C23 C22 C21 119.8(6) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 122.5(6) . . ? C22 C23 H23 118.7 . . ? C24 C23 H23 118.7 . . ? C25 C24 C23 118.1(6) . . ? C25 C24 H24 120.9 . . ? C23 C24 H24 120.9 . . ? C24 C25 C26 119.6(5) . . ? C24 C25 C27 119.1(6) . . ? C26 C25 C27 121.3(5) . . ? C21 C26 C25 121.7(5) . . ? C21 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? N3 C27 C25 111.6(5) . . ? N3 C27 H27A 109.3 . . ? C25 C27 H27A 109.3 . . ? N3 C27 H27B 109.3 . . ? C25 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? N4 C28 N3 110.6(5) . . ? N4 C28 H28 124.7 . . ? N3 C28 H28 124.7 . . ? C30 C29 N3 107.1(5) . . ? C30 C29 H29 126.5 . . ? N3 C29 H29 126.5 . . ? C29 C30 N4 108.8(5) . . ? C29 C30 H30 125.6 . . ? N4 C30 H30 125.6 . . ? 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 O7 H7B O3 0.85 2.23 2.901(7) 136.3 1_545 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.725 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 966844' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_20110430b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C76 H64 Cu5 N10 O28, 4(H2 O)' _chemical_formula_sum 'C76 H72 Cu5 N10 O32' _chemical_formula_weight 1955.14 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.1079(8) _cell_length_b 12.6464(8) _cell_length_c 15.5101(10) _cell_angle_alpha 81.140(2) _cell_angle_beta 67.910(2) _cell_angle_gamma 62.6250(10) _cell_volume 1953.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7558 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 28.01 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 999 _exptl_absorpt_coefficient_mu 1.436 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6892 _exptl_absorpt_correction_T_max 0.7525 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16100 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.10 _reflns_number_total 6823 _reflns_number_gt 5698 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.2000P)^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 6823 _refine_ls_number_parameters 556 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.2433 _refine_ls_wR_factor_gt 0.1844 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.5000 1.0000 1.0000 0.0210(3) Uani 1 2 d S . . Cu2 Cu 0.46836(5) 0.77333(5) 0.96723(4) 0.0253(2) Uani 1 1 d . . . Cu3 Cu 0.28672(5) 0.95016(5) 1.17266(4) 0.0273(2) Uani 1 1 d . . . O1 O 0.4463(4) 0.8728(3) 0.8566(2) 0.0339(8) Uani 1 1 d . . . O2 O 0.4977(4) 1.0185(3) 0.8672(3) 0.0360(9) Uani 1 1 d . . . O3 O 0.3799(5) 1.2358(5) 0.4475(3) 0.0670(14) Uani 1 1 d . . . O4 O 0.3429(3) 1.1645(3) 1.0356(3) 0.0347(8) Uani 1 1 d . . . O5 O 0.1911(3) 1.1174(3) 1.1422(3) 0.0364(8) Uani 1 1 d . . . O6 O -0.1397(7) 1.7595(5) 1.1228(5) 0.103(2) Uani 1 1 d . . . O7 O 0.3865(3) 0.7862(3) 1.2052(2) 0.0334(8) Uani 1 1 d . . . O8 O 0.5011(3) 0.6734(3) 1.0738(2) 0.0304(7) Uani 1 1 d . . . O9 O 0.6498(5) 0.2827(4) 1.4581(3) 0.0630(13) Uani 1 1 d . . . O10 O 0.1124(4) 0.8907(4) 1.1774(3) 0.0548(11) Uani 1 1 d . . . O11 O 0.0322(7) 0.8109(5) 1.3040(4) 0.0888(19) Uani 1 1 d . . . O12 O -0.0606(5) 0.9986(5) 1.2874(4) 0.0770(16) Uani 1 1 d . . . O14 O 0.2641(4) 0.7500(4) 1.0007(3) 0.0500(10) Uani 1 1 d . . . H14B H 0.1979 0.8182 1.0107 0.075 Uiso 1 1 d R . . H14C H 0.2711 0.7163 0.9543 0.075 Uiso 1 1 d R . . O13 O 0.3665(3) 0.9171(3) 1.0406(2) 0.0312(7) Uani 1 1 d . . . H13A H 0.3127 0.9428 1.0112 0.047 Uiso 1 1 d R . . O15 O 0.1513(4) 0.0394(4) 0.9709(3) 0.0558(11) Uani 1 1 d . . . H15A H 0.1717 0.0970 0.9631 0.084 Uiso 1 1 d R . . H15B H 0.1251 0.0380 0.9275 0.084 Uiso 1 1 d R . . O16 O 0.9030(4) 0.1071(4) 0.1123(3) 0.0624(13) Uani 1 1 d . . . H16A H 0.8769 0.1564 0.1554 0.094 Uiso 1 1 d R . . H16B H 0.9814 0.0942 0.0767 0.094 Uiso 1 1 d R . . N1 N 0.5873(4) 0.6338(3) 0.8820(3) 0.0267(8) Uani 1 1 d . . . N2 N 0.7256(4) 0.5294(4) 0.7528(3) 0.0326(9) Uani 1 1 d . . . N3 N 0.9263(4) 0.8753(4) 0.5729(3) 0.0342(10) Uani 1 1 d . . . N4 N 0.7988(4) 0.9978(4) 0.6944(3) 0.0310(9) Uani 1 1 d . . . N5 N 0.0285(5) 0.8990(5) 1.2557(4) 0.0482(12) Uani 1 1 d . . . C1 C 0.4615(4) 0.9667(4) 0.8293(3) 0.0266(10) Uani 1 1 d . . . C2 C 0.4303(4) 1.0183(4) 0.7430(3) 0.0273(10) Uani 1 1 d . . . C3 C 0.3619(6) 0.9824(6) 0.7091(4) 0.0433(13) Uani 1 1 d . . . H3 H 0.3346 0.9247 0.7398 0.052 Uiso 1 1 calc R . . C4 C 0.3343(7) 1.0319(6) 0.6302(5) 0.0538(16) Uani 1 1 d . . . H4 H 0.2859 1.0090 0.6091 0.065 Uiso 1 1 calc R . . C5 C 0.3765(5) 1.1140(5) 0.5820(4) 0.0405(13) Uani 1 1 d . . . C6 C 0.4439(6) 1.1525(5) 0.6167(4) 0.0390(12) Uani 1 1 d . . . H6 H 0.4727 1.2088 0.5846 0.047 Uiso 1 1 calc R . . C7 C 0.4676(5) 1.1084(5) 0.6969(4) 0.0351(11) Uani 1 1 d . . . H7 H 0.5081 1.1374 0.7212 0.042 Uiso 1 1 calc R . . C8 C 0.3537(7) 1.1621(7) 0.4940(5) 0.0570(17) Uani 1 1 d . . . H8 H 0.3132 1.1299 0.4725 0.068 Uiso 1 1 calc R . . C9 C 0.2281(5) 1.1887(4) 1.0917(3) 0.0290(10) Uani 1 1 d . . . C10 C 0.1266(5) 1.3161(4) 1.1001(3) 0.0275(10) Uani 1 1 d . . . C11 C 0.1627(5) 1.4058(5) 1.0573(4) 0.0357(11) Uani 1 1 d . . . H11 H 0.2495 1.3867 1.0178 0.043 Uiso 1 1 calc R . . C12 C 0.0707(6) 1.5219(5) 1.0731(4) 0.0456(14) Uani 1 1 d . . . H12 H 0.0963 1.5819 1.0464 0.055 Uiso 1 1 calc R . . C13 C -0.0611(6) 1.5522(5) 1.1287(4) 0.0414(12) Uani 1 1 d . . . C14 C -0.0993(5) 1.4619(5) 1.1711(4) 0.0445(13) Uani 1 1 d . . . H14 H -0.1868 1.4809 1.2087 0.053 Uiso 1 1 calc R . . C15 C -0.1608(8) 1.6771(6) 1.1474(6) 0.067(2) Uani 1 1 d . . . H15 H -0.2481 1.6913 1.1817 0.081 Uiso 1 1 calc R . . C16 C 0.4616(4) 0.6908(4) 1.1603(3) 0.0238(9) Uani 1 1 d . . . C17 C 0.5165(4) 0.5837(4) 1.2161(3) 0.0257(9) Uani 1 1 d . . . C18 C 0.5939(5) 0.4706(4) 1.1763(4) 0.0333(11) Uani 1 1 d . . . H18 H 0.6162 0.4603 1.1129 0.040 Uiso 1 1 calc R . . C19 C 0.6391(6) 0.3714(5) 1.2299(4) 0.0414(13) Uani 1 1 d . . . H19 H 0.6890 0.2957 1.2024 0.050 Uiso 1 1 calc R . . C20 C 0.6100(6) 0.3856(5) 1.3226(4) 0.0388(12) Uani 1 1 d . . . C21 C 0.5338(7) 0.4980(5) 1.3636(4) 0.0544(17) Uani 1 1 d . . . H21 H 0.5154 0.5080 1.4265 0.065 Uiso 1 1 calc R . . C22 C 0.4854(7) 0.5949(5) 1.3120(4) 0.0522(16) Uani 1 1 d . . . H22 H 0.4309 0.6696 1.3411 0.063 Uiso 1 1 calc R . . C23 C 0.6618(7) 0.2808(6) 1.3780(5) 0.0549(16) Uani 1 1 d . . . H23 H 0.7078 0.2066 1.3481 0.066 Uiso 1 1 calc R . . C24 C 0.6405(5) 0.5147(4) 0.9022(4) 0.0326(11) Uani 1 1 d . . . H24 H 0.6201 0.4841 0.9615 0.039 Uiso 1 1 calc R . . C25 C 0.7247(5) 0.4502(5) 0.8256(3) 0.0323(11) Uani 1 1 d . . . H25 H 0.7738 0.3678 0.8211 0.039 Uiso 1 1 calc R . . C26 C 0.6406(5) 0.6378(5) 0.7909(4) 0.0346(11) Uani 1 1 d . . . H26 H 0.6213 0.7076 0.7573 0.041 Uiso 1 1 calc R . . C27 C 0.8064(6) 0.5011(5) 0.6555(4) 0.0372(12) Uani 1 1 d . . . H27A H 0.7531 0.5484 0.6177 0.045 Uiso 1 1 calc R . . H27B H 0.8349 0.4178 0.6434 0.045 Uiso 1 1 calc R . . C28 C 0.9272(5) 0.5240(5) 0.6272(3) 0.0346(11) Uani 1 1 d . . . C29 C 1.0460(6) 0.4369(5) 0.6370(4) 0.0435(13) Uani 1 1 d . . . H29 H 1.0501 0.3645 0.6631 0.052 Uiso 1 1 calc R . . C30 C 1.1548(6) 0.4569(5) 0.6089(5) 0.0529(16) Uani 1 1 d . . . H30 H 1.2345 0.3970 0.6127 0.063 Uiso 1 1 calc R . . C31 C 1.1471(6) 0.5652(6) 0.5749(4) 0.0466(14) Uani 1 1 d . . . H31 H 1.2210 0.5795 0.5598 0.056 Uiso 1 1 calc R . . C32 C 1.0342(6) 0.6542(5) 0.5623(3) 0.0422(13) Uani 1 1 d . . . C33 C 0.9233(5) 0.6322(5) 0.5896(3) 0.0358(12) Uani 1 1 d . . . H33 H 0.8452 0.6911 0.5826 0.043 Uiso 1 1 calc R . . C34 C 1.0317(6) 0.7699(5) 0.5169(4) 0.0475(14) Uani 1 1 d . . . H34A H 1.1164 0.7697 0.5049 0.057 Uiso 1 1 calc R . . H34B H 1.0207 0.7742 0.4575 0.057 Uiso 1 1 calc R . . C35 C 0.8869(5) 0.8872(5) 0.6653(3) 0.0353(11) Uani 1 1 d . . . H35 H 0.9173 0.8256 0.7043 0.042 Uiso 1 1 calc R . . C36 C 0.8627(5) 0.9855(5) 0.5398(4) 0.0368(12) Uani 1 1 d . . . H36 H 0.8712 1.0054 0.4781 0.044 Uiso 1 1 calc R . . C37 C 0.7860(5) 1.0584(5) 0.6148(3) 0.0336(11) Uani 1 1 d . . . H37 H 0.7314 1.1391 0.6131 0.040 Uiso 1 1 calc R . . C38 C -0.0055(5) 1.3450(5) 1.1563(4) 0.0390(12) Uani 1 1 d . . . H38 H -0.0301 1.2847 1.1838 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0242(4) 0.0178(4) 0.0161(4) -0.0002(3) -0.0042(3) -0.0072(3) Cu2 0.0335(4) 0.0178(4) 0.0177(4) -0.0012(2) -0.0073(3) -0.0064(3) Cu3 0.0311(4) 0.0201(4) 0.0180(4) -0.0009(2) -0.0039(3) -0.0042(3) O1 0.051(2) 0.0256(18) 0.0254(18) 0.0044(14) -0.0174(16) -0.0155(16) O2 0.043(2) 0.039(2) 0.032(2) 0.0129(16) -0.0179(17) -0.0229(17) O3 0.076(3) 0.070(3) 0.044(3) 0.027(3) -0.030(2) -0.024(3) O4 0.0296(18) 0.0278(19) 0.038(2) 0.0036(16) -0.0052(16) -0.0110(15) O5 0.0405(19) 0.0166(17) 0.034(2) -0.0004(15) -0.0075(16) -0.0024(14) O6 0.117(5) 0.031(3) 0.112(5) 0.000(3) -0.017(4) -0.011(3) O7 0.0419(19) 0.0232(18) 0.0234(17) 0.0022(14) -0.0123(15) -0.0047(15) O8 0.0369(18) 0.0217(17) 0.0207(17) -0.0005(13) -0.0053(14) -0.0066(14) O9 0.090(3) 0.058(3) 0.044(3) 0.022(2) -0.036(3) -0.032(3) O10 0.055(3) 0.064(3) 0.040(2) -0.008(2) -0.007(2) -0.027(2) O11 0.128(5) 0.071(4) 0.060(3) 0.029(3) -0.030(3) -0.047(4) O12 0.044(3) 0.066(3) 0.092(4) -0.023(3) 0.000(3) -0.011(2) O14 0.046(2) 0.041(2) 0.048(2) -0.0013(19) -0.0151(19) -0.0071(18) O13 0.0361(18) 0.0237(17) 0.0208(16) -0.0034(13) -0.0090(14) -0.0021(14) O15 0.056(3) 0.054(3) 0.049(3) 0.004(2) -0.019(2) -0.018(2) O16 0.053(3) 0.051(3) 0.065(3) -0.006(2) -0.014(2) -0.011(2) N1 0.036(2) 0.0202(19) 0.023(2) 0.0002(16) -0.0117(17) -0.0099(16) N2 0.040(2) 0.026(2) 0.022(2) -0.0051(17) -0.0020(18) -0.0116(18) N3 0.045(2) 0.030(2) 0.020(2) 0.0001(17) -0.0053(18) -0.0149(19) N4 0.037(2) 0.025(2) 0.023(2) -0.0008(17) -0.0073(17) -0.0094(17) N5 0.051(3) 0.047(3) 0.044(3) 0.000(2) -0.015(2) -0.020(2) C1 0.027(2) 0.024(2) 0.019(2) 0.0024(18) -0.0063(18) -0.0056(18) C2 0.028(2) 0.021(2) 0.024(2) 0.0012(18) -0.0065(19) -0.0055(18) C3 0.053(3) 0.056(4) 0.034(3) 0.016(3) -0.016(3) -0.038(3) C4 0.068(4) 0.060(4) 0.060(4) 0.015(3) -0.044(4) -0.037(3) C5 0.033(3) 0.054(3) 0.024(3) 0.010(2) -0.009(2) -0.014(2) C6 0.049(3) 0.030(3) 0.043(3) 0.014(2) -0.022(3) -0.022(2) C7 0.039(3) 0.034(3) 0.035(3) 0.008(2) -0.014(2) -0.020(2) C8 0.066(4) 0.062(4) 0.045(4) 0.014(3) -0.034(3) -0.022(3) C9 0.032(2) 0.023(2) 0.028(2) 0.002(2) -0.010(2) -0.010(2) C10 0.033(2) 0.029(3) 0.022(2) 0.0034(19) -0.0124(19) -0.012(2) C11 0.042(3) 0.031(3) 0.037(3) 0.007(2) -0.019(2) -0.016(2) C12 0.055(3) 0.035(3) 0.055(4) 0.010(3) -0.028(3) -0.023(3) C13 0.046(3) 0.026(3) 0.041(3) -0.003(2) -0.015(3) -0.006(2) C14 0.035(3) 0.029(3) 0.052(3) 0.001(2) -0.010(3) -0.004(2) C15 0.066(4) 0.028(4) 0.087(6) 0.001(3) -0.025(4) -0.005(3) C16 0.024(2) 0.027(2) 0.017(2) 0.0012(18) -0.0052(17) -0.0100(19) C17 0.028(2) 0.024(2) 0.021(2) 0.0011(18) -0.0094(18) -0.0081(19) C18 0.049(3) 0.022(2) 0.029(3) 0.003(2) -0.020(2) -0.011(2) C19 0.054(3) 0.021(3) 0.045(3) 0.002(2) -0.025(3) -0.008(2) C20 0.058(3) 0.025(3) 0.039(3) 0.007(2) -0.025(3) -0.017(2) C21 0.076(4) 0.040(3) 0.023(3) 0.006(2) -0.016(3) -0.009(3) C22 0.079(4) 0.019(3) 0.040(3) -0.001(2) -0.034(3) 0.004(3) C23 0.083(5) 0.033(3) 0.057(4) 0.009(3) -0.044(4) -0.019(3) C24 0.042(3) 0.020(2) 0.035(3) 0.004(2) -0.014(2) -0.014(2) C25 0.037(3) 0.027(3) 0.028(3) 0.001(2) -0.014(2) -0.008(2) C26 0.046(3) 0.023(3) 0.026(3) -0.003(2) -0.007(2) -0.012(2) C27 0.047(3) 0.034(3) 0.021(3) -0.010(2) 0.002(2) -0.018(2) C28 0.044(3) 0.028(3) 0.020(2) -0.005(2) -0.005(2) -0.010(2) C29 0.051(3) 0.028(3) 0.035(3) -0.001(2) -0.010(2) -0.008(2) C30 0.048(3) 0.038(3) 0.060(4) -0.006(3) -0.025(3) -0.001(3) C31 0.035(3) 0.048(3) 0.041(3) -0.016(3) 0.003(2) -0.013(3) C32 0.055(3) 0.036(3) 0.014(2) -0.009(2) 0.008(2) -0.016(3) C33 0.037(3) 0.034(3) 0.021(2) -0.001(2) -0.006(2) -0.006(2) C34 0.059(3) 0.036(3) 0.025(3) -0.006(2) 0.002(2) -0.013(3) C35 0.045(3) 0.030(3) 0.019(2) -0.003(2) -0.003(2) -0.012(2) C36 0.034(3) 0.041(3) 0.026(3) 0.006(2) -0.003(2) -0.015(2) C37 0.032(2) 0.031(3) 0.023(2) 0.007(2) -0.004(2) -0.009(2) C38 0.032(3) 0.031(3) 0.045(3) 0.000(2) -0.011(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 2.043(3) . ? Cu1 O4 2.043(3) 2_677 ? Cu1 O2 2.047(4) . ? Cu1 O2 2.047(4) 2_677 ? Cu1 O13 2.167(4) . ? Cu1 O13 2.167(4) 2_677 ? Cu2 O13 1.908(3) . ? Cu2 O8 1.968(3) . ? Cu2 N1 1.971(4) . ? Cu2 O1 1.992(3) . ? Cu2 O14 2.477(4) . ? Cu2 H13A 2.0930 . ? Cu3 O13 1.925(3) . ? Cu3 O7 1.960(3) . ? Cu3 O5 1.972(3) . ? Cu3 N4 1.985(4) 2_677 ? Cu3 O10 2.520(5) . ? O1 C1 1.269(6) . ? O2 C1 1.243(6) . ? O3 C8 1.175(8) . ? O4 C9 1.250(6) . ? O5 C9 1.232(6) . ? O6 C15 1.160(9) . ? O7 C16 1.242(6) . ? O8 C16 1.261(6) . ? O9 C23 1.198(8) . ? O10 N5 1.238(7) . ? O11 N5 1.236(7) . ? O12 N5 1.239(7) . ? O14 H14B 0.8500 . ? O14 H14C 0.8500 . ? O13 H13A 0.8499 . ? O15 H15A 0.8500 . ? O15 H15B 0.8501 . ? O16 H16A 0.8501 . ? O16 H16B 0.8500 . ? N1 C26 1.319(7) . ? N1 C24 1.376(6) . ? N2 C26 1.335(7) . ? N2 C25 1.389(6) . ? N2 C27 1.447(6) . ? N3 C35 1.338(7) . ? N3 C36 1.375(7) . ? N3 C34 1.455(7) . ? N4 C35 1.327(7) . ? N4 C37 1.370(6) . ? N4 Cu3 1.985(4) 2_677 ? C1 C2 1.498(6) . ? C2 C3 1.384(8) . ? C2 C7 1.411(7) . ? C3 C4 1.371(8) . ? C3 H3 0.9300 . ? C4 C5 1.364(9) . ? C4 H4 0.9300 . ? C5 C6 1.403(8) . ? C5 C8 1.478(8) . ? C6 C7 1.359(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.498(6) . ? C10 C11 1.388(7) . ? C10 C38 1.402(7) . ? C11 C12 1.364(8) . ? C11 H11 0.9300 . ? C12 C13 1.395(8) . ? C12 H12 0.9300 . ? C13 C14 1.405(8) . ? C13 C15 1.470(8) . ? C14 C38 1.375(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.506(6) . ? C17 C18 1.382(7) . ? C17 C22 1.404(7) . ? C18 C19 1.397(7) . ? C18 H18 0.9300 . ? C19 C20 1.365(8) . ? C19 H19 0.9300 . ? C20 C21 1.382(8) . ? C20 C23 1.476(8) . ? C21 C22 1.369(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.319(7) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.510(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C33 1.389(8) . ? C28 C29 1.401(8) . ? C29 C30 1.353(9) . ? C29 H29 0.9300 . ? C30 C31 1.364(9) . ? C30 H30 0.9300 . ? C31 C32 1.375(9) . ? C31 H31 0.9300 . ? C32 C33 1.393(8) . ? C32 C34 1.514(8) . ? C33 H33 0.9300 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35 0.9300 . ? C36 C37 1.341(8) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 H38 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 O4 Cu1 O4 180.000(1) . 2_677 ? O4 Cu1 O2 90.03(16) . . ? O4 Cu1 O2 89.97(16) 2_677 . ? O4 Cu1 O2 89.97(16) . 2_677 ? O4 Cu1 O2 90.03(16) 2_677 2_677 ? O2 Cu1 O2 180.000(2) . 2_677 ? O4 Cu1 O13 90.80(13) . . ? O4 Cu1 O13 89.20(13) 2_677 . ? O2 Cu1 O13 90.77(13) . . ? O2 Cu1 O13 89.23(13) 2_677 . ? O4 Cu1 O13 89.20(13) . 2_677 ? O4 Cu1 O13 90.80(13) 2_677 2_677 ? O2 Cu1 O13 89.23(13) . 2_677 ? O2 Cu1 O13 90.77(13) 2_677 2_677 ? O13 Cu1 O13 180.000(1) . 2_677 ? O13 Cu2 O8 93.24(14) . . ? O13 Cu2 N1 173.13(15) . . ? O8 Cu2 N1 90.54(15) . . ? O13 Cu2 O1 87.78(14) . . ? O8 Cu2 O1 176.65(14) . . ? N1 Cu2 O1 88.13(15) . . ? O13 Cu2 O14 90.03(15) . . ? O8 Cu2 O14 90.01(15) . . ? N1 Cu2 O14 95.71(16) . . ? O1 Cu2 O14 93.18(15) . . ? O13 Cu2 H13A 24.0 . . ? O8 Cu2 H13A 111.3 . . ? N1 Cu2 H13A 155.9 . . ? O1 Cu2 H13A 70.5 . . ? O14 Cu2 H13A 75.0 . . ? O13 Cu3 O7 94.21(14) . . ? O13 Cu3 O5 86.81(14) . . ? O7 Cu3 O5 177.31(16) . . ? O13 Cu3 N4 173.87(15) . 2_677 ? O7 Cu3 N4 91.32(16) . 2_677 ? O5 Cu3 N4 87.56(16) . 2_677 ? O13 Cu3 O10 89.03(14) . . ? O7 Cu3 O10 87.77(16) . . ? O5 Cu3 O10 94.74(16) . . ? N4 Cu3 O10 93.84(16) 2_677 . ? C1 O1 Cu2 131.0(3) . . ? C1 O2 Cu1 127.9(3) . . ? C9 O4 Cu1 127.6(3) . . ? C9 O5 Cu3 133.0(3) . . ? C16 O7 Cu3 134.3(3) . . ? C16 O8 Cu2 135.4(3) . . ? N5 O10 Cu3 114.1(4) . . ? Cu2 O14 H14B 109.3 . . ? Cu2 O14 H14C 109.4 . . ? H14B O14 H14C 109.5 . . ? Cu2 O13 Cu3 133.35(18) . . ? Cu2 O13 Cu1 103.20(15) . . ? Cu3 O13 Cu1 101.13(15) . . ? Cu2 O13 H13A 90.3 . . ? Cu3 O13 H13A 115.4 . . ? Cu1 O13 H13A 113.2 . . ? H15A O15 H15B 109.5 . . ? H16A O16 H16B 109.5 . . ? C26 N1 C24 105.1(4) . . ? C26 N1 Cu2 125.4(3) . . ? C24 N1 Cu2 129.4(3) . . ? C26 N2 C25 106.3(4) . . ? C26 N2 C27 126.6(4) . . ? C25 N2 C27 127.0(4) . . ? C35 N3 C36 107.3(4) . . ? C35 N3 C34 126.0(5) . . ? C36 N3 C34 126.1(4) . . ? C35 N4 C37 104.7(4) . . ? C35 N4 Cu3 123.5(3) . 2_677 ? C37 N4 Cu3 131.8(3) . 2_677 ? O11 N5 O10 121.9(6) . . ? O11 N5 O12 118.9(6) . . ? O10 N5 O12 119.2(6) . . ? O2 C1 O1 126.7(4) . . ? O2 C1 C2 118.4(4) . . ? O1 C1 C2 115.0(4) . . ? C3 C2 C7 119.1(5) . . ? C3 C2 C1 121.5(4) . . ? C7 C2 C1 119.4(4) . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 121.4(5) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.9(5) . . ? C4 C5 C8 121.4(6) . . ? C6 C5 C8 119.7(5) . . ? C7 C6 C5 120.7(5) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 119.6(5) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O3 C8 C5 128.5(7) . . ? O3 C8 H8 115.7 . . ? C5 C8 H8 115.7 . . ? O5 C9 O4 125.8(4) . . ? O5 C9 C10 116.7(4) . . ? O4 C9 C10 117.5(4) . . ? C11 C10 C38 119.8(5) . . ? C11 C10 C9 121.0(4) . . ? C38 C10 C9 119.1(4) . . ? C12 C11 C10 119.9(5) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 121.0(5) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 119.6(5) . . ? C12 C13 C15 121.5(6) . . ? C14 C13 C15 118.9(6) . . ? C38 C14 C13 119.2(5) . . ? C38 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? O6 C15 C13 125.5(8) . . ? O6 C15 H15 117.3 . . ? C13 C15 H15 117.3 . . ? O7 C16 O8 128.0(4) . . ? O7 C16 C17 115.6(4) . . ? O8 C16 C17 116.3(4) . . ? C18 C17 C22 117.5(4) . . ? C18 C17 C16 121.7(4) . . ? C22 C17 C16 120.8(4) . . ? C17 C18 C19 121.0(5) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 120.1(5) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.8(5) . . ? C19 C20 C23 119.7(5) . . ? C21 C20 C23 120.5(6) . . ? C22 C21 C20 120.2(6) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 121.3(5) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? O9 C23 C20 125.8(6) . . ? O9 C23 H23 117.1 . . ? C20 C23 H23 117.1 . . ? C25 C24 N1 110.5(5) . . ? C25 C24 H24 124.8 . . ? N1 C24 H24 124.8 . . ? C24 C25 N2 106.5(4) . . ? C24 C25 H25 126.7 . . ? N2 C25 H25 126.7 . . ? N1 C26 N2 111.7(4) . . ? N1 C26 H26 124.2 . . ? N2 C26 H26 124.2 . . ? N2 C27 C28 112.8(4) . . ? N2 C27 H27A 109.0 . . ? C28 C27 H27A 109.0 . . ? N2 C27 H27B 109.0 . . ? C28 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C33 C28 C29 118.2(5) . . ? C33 C28 C27 120.6(5) . . ? C29 C28 C27 121.2(5) . . ? C30 C29 C28 120.8(5) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 119.7(6) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C30 C31 C32 122.5(6) . . ? C30 C31 H31 118.7 . . ? C32 C31 H31 118.7 . . ? C31 C32 C33 117.4(5) . . ? C31 C32 C34 121.5(6) . . ? C33 C32 C34 121.0(6) . . ? C28 C33 C32 121.2(5) . . ? C28 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? N3 C34 C32 113.5(5) . . ? N3 C34 H34A 108.9 . . ? C32 C34 H34A 108.9 . . ? N3 C34 H34B 108.9 . . ? C32 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? N4 C35 N3 111.4(5) . . ? N4 C35 H35 124.3 . . ? N3 C35 H35 124.3 . . ? C37 C36 N3 105.7(4) . . ? C37 C36 H36 127.2 . . ? N3 C36 H36 127.2 . . ? C36 C37 N4 110.9(5) . . ? C36 C37 H37 124.6 . . ? N4 C37 H37 124.6 . . ? C14 C38 C10 120.5(5) . . ? C14 C38 H38 119.7 . . ? C10 C38 H38 119.7 . . ? 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 O13 Cu2 O1 C1 47.5(4) . . . . ? O8 Cu2 O1 C1 -60(2) . . . . ? N1 Cu2 O1 C1 -127.0(4) . . . . ? O14 Cu2 O1 C1 137.4(4) . . . . ? O4 Cu1 O2 C1 -107.8(4) . . . . ? O4 Cu1 O2 C1 72.2(4) 2_677 . . . ? O2 Cu1 O2 C1 0(100) 2_677 . . . ? O13 Cu1 O2 C1 -17.1(4) . . . . ? O13 Cu1 O2 C1 162.9(4) 2_677 . . . ? O4 Cu1 O4 C9 -134(100) 2_677 . . . ? O2 Cu1 O4 C9 114.2(4) . . . . ? O2 Cu1 O4 C9 -65.8(4) 2_677 . . . ? O13 Cu1 O4 C9 23.5(4) . . . . ? O13 Cu1 O4 C9 -156.5(4) 2_677 . . . ? O13 Cu3 O5 C9 -53.9(5) . . . . ? O7 Cu3 O5 C9 58(3) . . . . ? N4 Cu3 O5 C9 123.6(5) 2_677 . . . ? O10 Cu3 O5 C9 -142.7(5) . . . . ? O13 Cu3 O7 C16 -7.9(5) . . . . ? O5 Cu3 O7 C16 -120(3) . . . . ? N4 Cu3 O7 C16 174.7(5) 2_677 . . . ? O10 Cu3 O7 C16 80.9(5) . . . . ? O13 Cu2 O8 C16 6.4(5) . . . . ? N1 Cu2 O8 C16 -179.3(4) . . . . ? O1 Cu2 O8 C16 114(2) . . . . ? O14 Cu2 O8 C16 -83.6(4) . . . . ? O13 Cu3 O10 N5 -179.3(4) . . . . ? O7 Cu3 O10 N5 86.5(4) . . . . ? O5 Cu3 O10 N5 -92.6(4) . . . . ? N4 Cu3 O10 N5 -4.7(4) 2_677 . . . ? O8 Cu2 O13 Cu3 -13.9(3) . . . . ? N1 Cu2 O13 Cu3 -137.2(12) . . . . ? O1 Cu2 O13 Cu3 169.3(3) . . . . ? O14 Cu2 O13 Cu3 76.1(3) . . . . ? O8 Cu2 O13 Cu1 105.66(15) . . . . ? N1 Cu2 O13 Cu1 -17.6(13) . . . . ? O1 Cu2 O13 Cu1 -71.14(15) . . . . ? O14 Cu2 O13 Cu1 -164.32(15) . . . . ? O7 Cu3 O13 Cu2 14.5(3) . . . . ? O5 Cu3 O13 Cu2 -168.0(3) . . . . ? N4 Cu3 O13 Cu2 168.8(13) 2_677 . . . ? O10 Cu3 O13 Cu2 -73.2(3) . . . . ? O7 Cu3 O13 Cu1 -105.84(15) . . . . ? O5 Cu3 O13 Cu1 71.66(15) . . . . ? N4 Cu3 O13 Cu1 48.4(15) 2_677 . . . ? O10 Cu3 O13 Cu1 166.46(16) . . . . ? O4 Cu1 O13 Cu2 154.39(17) . . . . ? O4 Cu1 O13 Cu2 -25.61(17) 2_677 . . . ? O2 Cu1 O13 Cu2 64.35(16) . . . . ? O2 Cu1 O13 Cu2 -115.65(16) 2_677 . . . ? O13 Cu1 O13 Cu2 -91(100) 2_677 . . . ? O4 Cu1 O13 Cu3 -65.73(16) . . . . ? O4 Cu1 O13 Cu3 114.27(16) 2_677 . . . ? O2 Cu1 O13 Cu3 -155.77(16) . . . . ? O2 Cu1 O13 Cu3 24.23(16) 2_677 . . . ? O13 Cu1 O13 Cu3 49(100) 2_677 . . . ? O13 Cu2 N1 C26 -39.1(15) . . . . ? O8 Cu2 N1 C26 -162.5(4) . . . . ? O1 Cu2 N1 C26 14.4(4) . . . . ? O14 Cu2 N1 C26 107.4(4) . . . . ? O13 Cu2 N1 C24 135.6(12) . . . . ? O8 Cu2 N1 C24 12.2(4) . . . . ? O1 Cu2 N1 C24 -170.9(4) . . . . ? O14 Cu2 N1 C24 -77.8(4) . . . . ? Cu3 O10 N5 O11 -101.9(6) . . . . ? Cu3 O10 N5 O12 76.8(6) . . . . ? Cu1 O2 C1 O1 -17.1(7) . . . . ? Cu1 O2 C1 C2 162.3(3) . . . . ? Cu2 O1 C1 O2 1.5(7) . . . . ? Cu2 O1 C1 C2 -177.9(3) . . . . ? O2 C1 C2 C3 -165.3(5) . . . . ? O1 C1 C2 C3 14.2(7) . . . . ? O2 C1 C2 C7 12.6(7) . . . . ? O1 C1 C2 C7 -168.0(4) . . . . ? C7 C2 C3 C4 1.8(9) . . . . ? C1 C2 C3 C4 179.6(6) . . . . ? C2 C3 C4 C5 2.0(11) . . . . ? C3 C4 C5 C6 -3.1(10) . . . . ? C3 C4 C5 C8 176.3(6) . . . . ? C4 C5 C6 C7 0.3(9) . . . . ? C8 C5 C6 C7 -179.1(6) . . . . ? C5 C6 C7 C2 3.4(8) . . . . ? C3 C2 C7 C6 -4.5(8) . . . . ? C1 C2 C7 C6 177.6(5) . . . . ? C4 C5 C8 O3 176.9(8) . . . . ? C6 C5 C8 O3 -3.7(11) . . . . ? Cu3 O5 C9 O4 9.6(8) . . . . ? Cu3 O5 C9 C10 -169.0(3) . . . . ? Cu1 O4 C9 O5 6.4(8) . . . . ? Cu1 O4 C9 C10 -175.0(3) . . . . ? O5 C9 C10 C11 170.1(5) . . . . ? O4 C9 C10 C11 -8.6(7) . . . . ? O5 C9 C10 C38 -6.6(7) . . . . ? O4 C9 C10 C38 174.7(5) . . . . ? C38 C10 C11 C12 2.8(8) . . . . ? C9 C10 C11 C12 -173.9(5) . . . . ? C10 C11 C12 C13 -2.8(9) . . . . ? C11 C12 C13 C14 1.7(9) . . . . ? C11 C12 C13 C15 179.1(6) . . . . ? C12 C13 C14 C38 -0.4(9) . . . . ? C15 C13 C14 C38 -178.0(6) . . . . ? C12 C13 C15 O6 -4.0(13) . . . . ? C14 C13 C15 O6 173.5(9) . . . . ? Cu3 O7 C16 O8 3.2(8) . . . . ? Cu3 O7 C16 C17 -179.5(3) . . . . ? Cu2 O8 C16 O7 -2.2(8) . . . . ? Cu2 O8 C16 C17 -179.5(3) . . . . ? O7 C16 C17 C18 175.4(4) . . . . ? O8 C16 C17 C18 -7.0(6) . . . . ? O7 C16 C17 C22 -1.6(7) . . . . ? O8 C16 C17 C22 176.0(5) . . . . ? C22 C17 C18 C19 0.0(8) . . . . ? C16 C17 C18 C19 -177.1(5) . . . . ? C17 C18 C19 C20 -1.7(8) . . . . ? C18 C19 C20 C21 1.1(9) . . . . ? C18 C19 C20 C23 -178.0(6) . . . . ? C19 C20 C21 C22 1.2(10) . . . . ? C23 C20 C21 C22 -179.6(7) . . . . ? C20 C21 C22 C17 -3.0(11) . . . . ? C18 C17 C22 C21 2.3(10) . . . . ? C16 C17 C22 C21 179.4(6) . . . . ? C19 C20 C23 O9 175.2(7) . . . . ? C21 C20 C23 O9 -3.9(11) . . . . ? C26 N1 C24 C25 1.1(6) . . . . ? Cu2 N1 C24 C25 -174.5(4) . . . . ? N1 C24 C25 N2 -0.6(6) . . . . ? C26 N2 C25 C24 -0.1(6) . . . . ? C27 N2 C25 C24 177.5(5) . . . . ? C24 N1 C26 N2 -1.2(6) . . . . ? Cu2 N1 C26 N2 174.6(3) . . . . ? C25 N2 C26 N1 0.8(6) . . . . ? C27 N2 C26 N1 -176.8(5) . . . . ? C26 N2 C27 C28 78.0(7) . . . . ? C25 N2 C27 C28 -99.2(6) . . . . ? N2 C27 C28 C33 -93.4(6) . . . . ? N2 C27 C28 C29 87.2(6) . . . . ? C33 C28 C29 C30 -1.3(9) . . . . ? C27 C28 C29 C30 178.1(6) . . . . ? C28 C29 C30 C31 3.4(10) . . . . ? C29 C30 C31 C32 -4.2(10) . . . . ? C30 C31 C32 C33 2.9(9) . . . . ? C30 C31 C32 C34 -174.7(6) . . . . ? C29 C28 C33 C32 0.0(8) . . . . ? C27 C28 C33 C32 -179.4(5) . . . . ? C31 C32 C33 C28 -0.7(8) . . . . ? C34 C32 C33 C28 176.8(5) . . . . ? C35 N3 C34 C32 39.7(9) . . . . ? C36 N3 C34 C32 -150.3(6) . . . . ? C31 C32 C34 N3 -125.8(6) . . . . ? C33 C32 C34 N3 56.7(8) . . . . ? C37 N4 C35 N3 -1.6(6) . . . . ? Cu3 N4 C35 N3 178.4(3) 2_677 . . . ? C36 N3 C35 N4 1.6(6) . . . . ? C34 N3 C35 N4 173.2(5) . . . . ? C35 N3 C36 C37 -0.9(6) . . . . ? C34 N3 C36 C37 -172.5(5) . . . . ? N3 C36 C37 N4 -0.1(6) . . . . ? C35 N4 C37 C36 1.0(6) . . . . ? Cu3 N4 C37 C36 -179.0(4) 2_677 . . . ? C13 C14 C38 C10 0.4(9) . . . . ? C11 C10 C38 C14 -1.6(8) . . . . ? C9 C10 C38 C14 175.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O14 H14B O16 0.85 2.48 2.960(6) 116.4 2_666 O14 H14B O10 0.85 2.54 2.959(6) 111.7 . O14 H14B O15 0.85 2.61 3.292(6) 138.2 1_565 O13 H13A O15 0.85 2.05 2.872(6) 163.7 1_565 O15 H15A O6 0.85 2.05 2.699(7) 132.4 2_577 O15 H15B O16 0.85 2.22 2.833(7) 128.5 2_656 O16 H16B O15 0.85 1.98 2.799(6) 162.4 1_654 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.350 _refine_diff_density_min -1.041 _refine_diff_density_rms 0.210 _database_code_depnum_ccdc_archive 'CCDC 966855' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_20110611a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 Cu N4 O6' _chemical_formula_sum 'C30 H24 Cu N4 O6' _chemical_formula_weight 600.07 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' Cu Cu 0.3201 1.2651 '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' _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' _cell_length_a 7.832(4) _cell_length_b 8.407(5) _cell_length_c 10.143(6) _cell_angle_alpha 84.772(8) _cell_angle_beta 83.075(7) _cell_angle_gamma 80.351(7) _cell_volume 651.9(6) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4985 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.21 _exptl_crystal_description Block _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 309 _exptl_absorpt_coefficient_mu 0.892 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8348 _exptl_absorpt_correction_T_max 0.8778 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5562 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2395 _reflns_number_gt 2253 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.1286P)^2^+0.0322P] 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 2395 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.0000 0.0345(2) Uani 1 2 d S . . O1 O 0.6951(3) 0.5103(2) 0.0968(2) 0.0424(5) Uani 1 1 d . . . O2 O 0.5058(3) 0.6730(3) 0.2174(3) 0.0615(6) Uani 1 1 d . . . O3 O 1.1919(5) 0.7915(4) 0.5594(3) 0.0902(11) Uani 1 1 d . . . N1 N 0.4352(3) 0.3198(3) 0.1226(2) 0.0374(5) Uani 1 1 d . . . N2 N 0.3081(3) 0.1166(3) 0.2047(2) 0.0403(5) Uani 1 1 d . . . C1 C 0.6528(4) 0.6040(3) 0.1886(3) 0.0423(7) Uani 1 1 d . . . C2 C 0.7966(4) 0.6275(3) 0.2642(3) 0.0375(6) Uani 1 1 d . . . C3 C 0.9638(4) 0.5531(4) 0.2315(3) 0.0496(7) Uani 1 1 d . . . H3 H 0.9881 0.4861 0.1613 0.060 Uiso 1 1 calc R . . C4 C 1.0948(4) 0.5766(4) 0.3009(3) 0.0511(8) Uani 1 1 d . . . H4 H 1.2080 0.5259 0.2773 0.061 Uiso 1 1 calc R . . C5 C 1.0619(4) 0.6734(4) 0.4045(3) 0.0413(6) Uani 1 1 d . . . C6 C 0.8958(5) 0.7475(5) 0.4363(4) 0.0627(9) Uani 1 1 d . . . H6 H 0.8716 0.8151 0.5061 0.075 Uiso 1 1 calc R . . C7 C 0.7648(4) 0.7241(5) 0.3675(4) 0.0587(9) Uani 1 1 d . . . H7 H 0.6518 0.7750 0.3915 0.070 Uiso 1 1 calc R . . C8 C 1.2029(5) 0.6972(5) 0.4780(4) 0.0570(9) Uani 1 1 d . . . H8 H 1.3105 0.6331 0.4593 0.068 Uiso 1 1 calc R . . C9 C 0.5070(4) 0.2537(4) 0.2348(3) 0.0450(7) Uani 1 1 d . . . H9 H 0.5964 0.2896 0.2705 0.054 Uiso 1 1 calc R . . C10 C 0.4288(4) 0.1296(4) 0.2851(3) 0.0494(7) Uani 1 1 d . . . H10 H 0.4530 0.0640 0.3617 0.059 Uiso 1 1 calc R . . C11 C 0.3148(4) 0.2335(3) 0.1088(3) 0.0402(6) Uani 1 1 d . . . H11 H 0.2432 0.2521 0.0403 0.048 Uiso 1 1 calc R . . C12 C 0.1901(4) -0.0046(4) 0.2230(3) 0.0492(7) Uani 1 1 d . . . H12A H 0.2579 -0.1113 0.2370 0.059 Uiso 1 1 calc R . . H12B H 0.1094 0.0157 0.3022 0.059 Uiso 1 1 calc R . . C13 C 0.0910(4) -0.0027(3) 0.1087(3) 0.0402(6) Uani 1 1 d . . . C14 C 0.1567(5) -0.0947(4) 0.0061(4) 0.0600(9) Uani 1 1 d . . . H14 H 0.2640 -0.1611 0.0093 0.072 Uiso 1 1 calc R . . C15 C -0.0672(5) 0.0914(5) 0.1024(4) 0.0617(9) Uani 1 1 d . . . H15 H -0.1153 0.1543 0.1725 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0283(3) 0.0380(3) 0.0413(3) -0.00668(19) -0.01059(19) -0.01020(19) O1 0.0372(10) 0.0479(11) 0.0475(12) -0.0052(9) -0.0143(8) -0.0143(8) O2 0.0323(11) 0.0733(15) 0.0814(17) -0.0176(13) -0.0158(11) -0.0020(10) O3 0.097(2) 0.105(2) 0.085(2) -0.0307(18) -0.0547(19) -0.0171(19) N1 0.0329(11) 0.0421(12) 0.0407(12) -0.0044(9) -0.0099(9) -0.0107(9) N2 0.0381(12) 0.0432(12) 0.0425(13) -0.0004(10) -0.0074(10) -0.0138(10) C1 0.0341(14) 0.0431(14) 0.0519(17) 0.0039(12) -0.0098(12) -0.0129(11) C2 0.0326(13) 0.0376(13) 0.0444(15) -0.0006(11) -0.0072(11) -0.0104(10) C3 0.0351(15) 0.0620(18) 0.0552(18) -0.0228(14) -0.0081(13) -0.0050(13) C4 0.0310(14) 0.070(2) 0.0554(18) -0.0168(15) -0.0103(12) -0.0077(13) C5 0.0447(15) 0.0487(15) 0.0360(14) 0.0006(11) -0.0132(12) -0.0183(12) C6 0.058(2) 0.078(2) 0.057(2) -0.0326(17) -0.0172(16) -0.0031(17) C7 0.0417(17) 0.072(2) 0.063(2) -0.0273(16) -0.0115(15) 0.0050(15) C8 0.057(2) 0.071(2) 0.0502(18) 0.0047(16) -0.0228(15) -0.0231(16) C9 0.0366(14) 0.0543(16) 0.0474(16) -0.0060(12) -0.0142(12) -0.0087(12) C10 0.0445(16) 0.0602(18) 0.0446(16) 0.0037(14) -0.0142(13) -0.0087(14) C11 0.0393(14) 0.0431(14) 0.0418(15) -0.0009(11) -0.0114(11) -0.0128(11) C12 0.0531(18) 0.0494(16) 0.0493(17) 0.0024(13) -0.0067(13) -0.0229(14) C13 0.0385(14) 0.0361(13) 0.0482(16) -0.0033(11) -0.0017(11) -0.0140(11) C14 0.0421(17) 0.066(2) 0.071(2) -0.0248(17) -0.0116(15) 0.0083(15) C15 0.0488(19) 0.073(2) 0.064(2) -0.0355(17) -0.0001(16) -0.0003(16) _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 1.931(2) . ? Cu1 O1 1.931(2) 2_665 ? Cu1 N1 1.965(2) . ? Cu1 N1 1.965(2) 2_665 ? O1 C1 1.253(4) . ? O2 C1 1.213(4) . ? O3 C8 1.182(5) . ? N1 C11 1.310(4) . ? N1 C9 1.362(4) . ? N2 C11 1.321(4) . ? N2 C10 1.345(4) . ? N2 C12 1.472(4) . ? C1 C2 1.485(4) . ? C2 C7 1.359(5) . ? C2 C3 1.369(4) . ? C3 C4 1.362(5) . ? C3 H3 0.9300 . ? C4 C5 1.361(5) . ? C4 H4 0.9300 . ? C5 C6 1.359(5) . ? C5 C8 1.454(4) . ? C6 C7 1.358(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.328(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.469(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.353(5) . ? C13 C15 1.359(5) . ? C14 C15 1.370(5) 2 ? C14 H14 0.9300 . ? C15 C14 1.370(5) 2 ? C15 H15 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 O1 180.0 . 2_665 ? O1 Cu1 N1 90.57(10) . . ? O1 Cu1 N1 89.43(10) 2_665 . ? O1 Cu1 N1 89.43(10) . 2_665 ? O1 Cu1 N1 90.57(10) 2_665 2_665 ? N1 Cu1 N1 180.00(9) . 2_665 ? C1 O1 Cu1 111.44(18) . . ? C11 N1 C9 105.4(2) . . ? C11 N1 Cu1 125.9(2) . . ? C9 N1 Cu1 128.6(2) . . ? C11 N2 C10 107.1(3) . . ? C11 N2 C12 127.2(3) . . ? C10 N2 C12 125.7(3) . . ? O2 C1 O1 124.2(3) . . ? O2 C1 C2 120.2(3) . . ? O1 C1 C2 115.5(2) . . ? C7 C2 C3 118.4(3) . . ? C7 C2 C1 120.5(3) . . ? C3 C2 C1 121.1(3) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 118.6(3) . . ? C6 C5 C8 121.3(3) . . ? C4 C5 C8 120.1(3) . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C2 C7 C6 120.9(3) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? O3 C8 C5 125.3(4) . . ? O3 C8 H8 117.3 . . ? C5 C8 H8 117.3 . . ? C10 C9 N1 109.1(3) . . ? C10 C9 H9 125.5 . . ? N1 C9 H9 125.5 . . ? C9 C10 N2 107.2(3) . . ? C9 C10 H10 126.4 . . ? N2 C10 H10 126.4 . . ? N1 C11 N2 111.2(3) . . ? N1 C11 H11 124.4 . . ? N2 C11 H11 124.4 . . ? C13 C12 N2 112.7(2) . . ? C13 C12 H12A 109.0 . . ? N2 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? N2 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C15 118.4(3) . . ? C14 C13 C12 120.3(3) . . ? C15 C13 C12 121.3(3) . . ? C13 C14 C15 120.9(3) . 2 ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 2 . ? C13 C15 C14 120.7(3) . 2 ? C13 C15 H15 119.6 . . ? C14 C15 H15 119.6 2 . ? 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 O1 Cu1 O1 C1 39(100) 2_665 . . . ? N1 Cu1 O1 C1 -89.7(2) . . . . ? N1 Cu1 O1 C1 90.3(2) 2_665 . . . ? O1 Cu1 N1 C11 -172.3(2) . . . . ? O1 Cu1 N1 C11 7.7(2) 2_665 . . . ? N1 Cu1 N1 C11 171(100) 2_665 . . . ? O1 Cu1 N1 C9 4.9(3) . . . . ? O1 Cu1 N1 C9 -175.1(3) 2_665 . . . ? N1 Cu1 N1 C9 -12(100) 2_665 . . . ? Cu1 O1 C1 O2 3.6(4) . . . . ? Cu1 O1 C1 C2 -176.66(17) . . . . ? O2 C1 C2 C7 1.0(4) . . . . ? O1 C1 C2 C7 -178.7(3) . . . . ? O2 C1 C2 C3 -178.7(3) . . . . ? O1 C1 C2 C3 1.5(4) . . . . ? C7 C2 C3 C4 -0.3(5) . . . . ? C1 C2 C3 C4 179.5(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C3 C4 C5 C8 179.9(3) . . . . ? C4 C5 C6 C7 0.8(6) . . . . ? C8 C5 C6 C7 -179.8(3) . . . . ? C3 C2 C7 C6 0.5(5) . . . . ? C1 C2 C7 C6 -179.3(3) . . . . ? C5 C6 C7 C2 -0.7(6) . . . . ? C6 C5 C8 O3 -8.0(6) . . . . ? C4 C5 C8 O3 171.4(4) . . . . ? C11 N1 C9 C10 0.2(4) . . . . ? Cu1 N1 C9 C10 -177.4(2) . . . . ? N1 C9 C10 N2 0.2(4) . . . . ? C11 N2 C10 C9 -0.6(3) . . . . ? C12 N2 C10 C9 -179.8(3) . . . . ? C9 N1 C11 N2 -0.6(3) . . . . ? Cu1 N1 C11 N2 177.12(18) . . . . ? C10 N2 C11 N1 0.8(3) . . . . ? C12 N2 C11 N1 179.9(3) . . . . ? C11 N2 C12 C13 9.3(5) . . . . ? C10 N2 C12 C13 -171.7(3) . . . . ? N2 C12 C13 C14 89.1(4) . . . . ? N2 C12 C13 C15 -90.5(4) . . . . ? C15 C13 C14 C15 0.9(6) . . . 2 ? C12 C13 C14 C15 -178.6(3) . . . 2 ? C14 C13 C15 C14 -0.9(6) . . . 2 ? C12 C13 C15 C14 178.6(3) . . . 2 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.470 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 966856'